Datasets:
haydn-jones
/
ORD-RXN-Insight

Dataset card Data Studio Files
xet
 Community
1
dataset_id
large_stringclasses
414 values
reaction_id
large_stringlengths
36
36
reaction_smiles
large_stringlengths
4
873
rxn_insight_reaction
large_stringlengths
19
1.07k
mapped_reaction_smiles
large_stringlengths
14
3.37k
reactant_smiles
large_stringlengths
1
581
product_smiles
large_stringlengths
1
433
reagent_smiles
large_stringclasses
634 values
catalyst_smiles
large_stringlengths
1
683
⌀
solvent_smiles
large_stringlengths
1
245
⌀
rxn_insight_class
large_stringclasses
11 values
rxn_insight_name
large_stringclasses
346 values
rxn_insight_tag
large_stringlengths
64
64
rxn_insight_tag2
large_stringlengths
64
64
rxn_insight_scaffold
large_stringlengths
5
288
⌀
rxn_insight_template
large_stringlengths
24
2.64k
⌀
yield_percent
float64
-0.8
90,205,160,000B
⌀
yield_measurements
large_stringlengths
2
864
temperature_value
float64
-230
30.1k
⌀
temperature_units
large_stringclasses
3 values
reaction_time_value
float64
0
4k
⌀
time_units
large_stringclasses
4 values
procedure_details
large_stringlengths
1
23.6k
⌀
reference
large_stringclasses
96 values
doi
large_stringclasses
19 values
functional_groups_reactants
large_stringlengths
3
716
⌀
functional_groups_products
large_stringlengths
3
539
⌀
participating_rings_reactants
large_stringlengths
5
293
⌀
participating_rings_products
large_stringlengths
5
271
⌀
all_rings_products
large_stringlengths
5
271
⌀
byproduct_smiles
large_stringclasses
176 values
agent_smiles
large_stringlengths
1
712
⌀
temperature_c
float64
-230
30.1k
⌀
reaction_time_hours
float64
0
2.16k
⌀
reaction_smiles_with_agents
large_stringlengths
4
882
ord_dataset-0316886541d9435489859c2ad7edc863
ord-2c3a22b0503044e4acce0cc88c40423f
C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]...
C=Cc1ccccc1.Ic1ccccc1
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1
CN(C)C=O
Aromatic Heterocycle Formation
Heck terminal vinyl
87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2
b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Aromatic halide.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
I-
CCN(CC)CC.c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1.CN(C)C=O
85
16
C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-27f7ca92b8f74e7db212a9a40682f54c
C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]...
C=Cc1ccccc1.Ic1ccccc1
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C
CN(C)C=O
Aromatic Heterocycle Formation
Heck terminal vinyl
87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2
b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Aromatic halide.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
I-
CCN(CC)CC.CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.CN(C)C=O
85
16
C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-fced571b80504a8ab131671fd45b015a
C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]...
C=Cc1ccccc1.Ic1ccccc1
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
[B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C
CN(C)C=O
Aromatic Heterocycle Formation
Heck terminal vinyl
87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2
b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Aromatic halide.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
I-
CCN(CC)CC.[B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C.CN(C)C=O
85
16
C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.[B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-5d8bd33fe0e147f5951b8a6d1257bbfa
C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]...
C=Cc1ccccc1.Ic1ccccc1
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
c1ccccc1P(c2ccccc2)c3ccccc3
CN(C)C=O
Aromatic Heterocycle Formation
Heck terminal vinyl
87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2
b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Aromatic halide.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
I-
CCN(CC)CC.c1ccccc1P(c2ccccc2)c3ccccc3.CN(C)C=O
85
16
C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.c1ccccc1P(c2ccccc2)c3ccccc3.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-06f7d0ee90f0414f95c64695a85cadd0
C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]...
C=Cc1ccccc1.Ic1ccccc1
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-]
CN(C)C=O
Aromatic Heterocycle Formation
Heck terminal vinyl
87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2
b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Aromatic halide.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
I-
CCN(CC)CC.CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-].CN(C)C=O
85
16
C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-].CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-1a22825cffea4334acbee02760d8595b
C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]...
C=Cc1ccccc1.Ic1ccccc1
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4
CN(C)C=O
Aromatic Heterocycle Formation
Heck terminal vinyl
87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2
b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Aromatic halide.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
I-
CCN(CC)CC.CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4.CN(C)C=O
85
16
C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-ca9dd53ebd5d40ca8463d93e411c4c2c
C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]...
C=Cc1ccccc1.Ic1ccccc1
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
c1cc2ccc3cccnc3c2nc1
CN(C)C=O
Aromatic Heterocycle Formation
Heck terminal vinyl
87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2
b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Aromatic halide.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
I-
CCN(CC)CC.c1cc2ccc3cccnc3c2nc1.CN(C)C=O
85
16
C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.c1cc2ccc3cccnc3c2nc1.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-a430f80373924da0957c25c0b0cac956
C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]...
C=Cc1ccccc1.Ic1ccccc1
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C
CN(C)C=O
Aromatic Heterocycle Formation
Heck terminal vinyl
87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2
b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Aromatic halide.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
I-
CCN(CC)CC.O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C.CN(C)C=O
85
16
C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-14c4c5b5713541fbacb1c220a66e7b9a
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]...
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1
CN(C)C=O
Aromatic Heterocycle Formation
OtherReaction
2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6
852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Triflate.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
null
CCN(CC)CC.FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1.CN(C)C=O
85
16
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-7aff19915647405998c64b0c3a4cce95
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]...
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2
CN(C)C=O
Aromatic Heterocycle Formation
OtherReaction
2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6
852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Triflate.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
null
CCN(CC)CC.FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2.CN(C)C=O
85
16
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-eecb993fad7f42d3809d0c093298a57d
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]...
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1
CN(C)C=O
Aromatic Heterocycle Formation
OtherReaction
2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6
852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Triflate.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
null
CCN(CC)CC.CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1.CN(C)C=O
85
16
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-0bd1f8bc6ec543b99d6c628aab7fcf6f
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]...
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4
CN(C)C=O
Aromatic Heterocycle Formation
OtherReaction
2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6
852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Triflate.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
null
CCN(CC)CC.C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.CN(C)C=O
85
16
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-7d52d0ac2d1a4af3b20abe6bb2430348
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]...
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1
CN(C)C=O
Aromatic Heterocycle Formation
OtherReaction
2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6
852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Triflate.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
null
CCN(CC)CC.c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1.CN(C)C=O
85
16
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-85fb7a759f8d4113ad204dd15049bf40
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]...
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C
CN(C)C=O
Aromatic Heterocycle Formation
OtherReaction
2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6
852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Triflate.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
null
CCN(CC)CC.CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.CN(C)C=O
85
16
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-01215af690f9499f955accd03d554c4b
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]...
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
[B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C
CN(C)C=O
Aromatic Heterocycle Formation
OtherReaction
2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6
852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Triflate.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
null
CCN(CC)CC.[B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C.CN(C)C=O
85
16
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.[B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-b6c1472cfcfd4c4db8872ab5e354553d
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]...
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
c1ccccc1P(c2ccccc2)c3ccccc3
CN(C)C=O
Aromatic Heterocycle Formation
OtherReaction
2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6
852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Triflate.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
null
CCN(CC)CC.c1ccccc1P(c2ccccc2)c3ccccc3.CN(C)C=O
85
16
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.c1ccccc1P(c2ccccc2)c3ccccc3.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-e4e693bc0f5f4bfc8826081a4308a820
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]...
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-]
CN(C)C=O
Aromatic Heterocycle Formation
OtherReaction
2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6
852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Triflate.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
null
CCN(CC)CC.CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-].CN(C)C=O
85
16
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-].CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-e87cad79ea714b35aa51bde91a2df44e
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]...
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4
CN(C)C=O
Aromatic Heterocycle Formation
OtherReaction
2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6
852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Triflate.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
null
CCN(CC)CC.CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4.CN(C)C=O
85
16
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-0e335301320e46229389c4eba0405b9f
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]...
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
c1cc2ccc3cccnc3c2nc1
CN(C)C=O
Aromatic Heterocycle Formation
OtherReaction
2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6
852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Triflate.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
null
CCN(CC)CC.c1cc2ccc3cccnc3c2nc1.CN(C)C=O
85
16
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.c1cc2ccc3cccnc3c2nc1.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-42cc0d35278c4a3eb39846d429e18282
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]...
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C
CN(C)C=O
Aromatic Heterocycle Formation
OtherReaction
2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6
852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Triflate.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
null
CCN(CC)CC.O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C.CN(C)C=O
85
16
C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-860887e0bf9c42d484f6ad6256eff82b
C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]...
C=Cc1ccccc1.Ic1ccccc1
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1
CN(C)C=O
Aromatic Heterocycle Formation
Heck terminal vinyl
87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2
b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Aromatic halide.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
I-
CCN(CC)CC.FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1.CN(C)C=O
85
16
C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-4ff33f54b13b4a5aacf575dc7a939eb8
C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]...
C=Cc1ccccc1.Ic1ccccc1
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2
CN(C)C=O
Aromatic Heterocycle Formation
Heck terminal vinyl
87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2
b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Aromatic halide.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
I-
CCN(CC)CC.FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2.CN(C)C=O
85
16
C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-fbddc104fed14a80aad4ff7609ddae2c
C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]...
C=Cc1ccccc1.Ic1ccccc1
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1
CN(C)C=O
Aromatic Heterocycle Formation
Heck terminal vinyl
87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2
b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Aromatic halide.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
I-
CCN(CC)CC.CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1.CN(C)C=O
85
16
C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-21d15dcb1bde46f2812e02686e79278a
C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]...
C=Cc1ccccc1.Ic1ccccc1
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4
CN(C)C=O
Aromatic Heterocycle Formation
Heck terminal vinyl
87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2
b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Aromatic halide.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
I-
CCN(CC)CC.C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.CN(C)C=O
85
16
C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-edee93962c894fd5ab7a9a40961daf4e
C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]...
C=Cc1ccccc1.Ic1ccccc1
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1
CN(C)C=O
Aromatic Heterocycle Formation
Heck terminal vinyl
87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2
b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Aromatic halide.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
I-
CCN(CC)CC.c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1.CN(C)C=O
85
16
C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-4f9475005ea447a0aefc36c204c2e0b0
C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]...
C=Cc1ccccc1.Ic1ccccc1
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C
CN(C)C=O
Aromatic Heterocycle Formation
Heck terminal vinyl
87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2
b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Aromatic halide.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
I-
CCN(CC)CC.CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.CN(C)C=O
85
16
C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-258eb46a1af5427b8bd3b37d8154c2f2
C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]...
C=Cc1ccccc1.Ic1ccccc1
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
[B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C
CN(C)C=O
Aromatic Heterocycle Formation
Heck terminal vinyl
87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2
b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Aromatic halide.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
I-
CCN(CC)CC.[B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C.CN(C)C=O
85
16
C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.[B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-6baee24ccd5f446e9f4dc2d69b422a15
C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]...
C=Cc1ccccc1.Ic1ccccc1
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
c1ccccc1P(c2ccccc2)c3ccccc3
CN(C)C=O
Aromatic Heterocycle Formation
Heck terminal vinyl
87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2
b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Aromatic halide.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
I-
CCN(CC)CC.c1ccccc1P(c2ccccc2)c3ccccc3.CN(C)C=O
85
16
C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.c1ccccc1P(c2ccccc2)c3ccccc3.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-17495cd43c444c9eac9f7f4a6ebc9b85
C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]...
C=Cc1ccccc1.Ic1ccccc1
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-]
CN(C)C=O
Aromatic Heterocycle Formation
Heck terminal vinyl
87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2
b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Aromatic halide.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
I-
CCN(CC)CC.CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-].CN(C)C=O
85
16
C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-].CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-d7823a08c2664306b03d5f8e9ca5c7c9
C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]...
C=Cc1ccccc1.Ic1ccccc1
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4
CN(C)C=O
Aromatic Heterocycle Formation
Heck terminal vinyl
87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2
b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Aromatic halide.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
I-
CCN(CC)CC.CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4.CN(C)C=O
85
16
C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-a115354853db41c1aff7c64396a06e2d
C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]...
C=Cc1ccccc1.Ic1ccccc1
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
c1cc2ccc3cccnc3c2nc1
CN(C)C=O
Aromatic Heterocycle Formation
Heck terminal vinyl
87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2
b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Aromatic halide.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
I-
CCN(CC)CC.c1cc2ccc3cccnc3c2nc1.CN(C)C=O
85
16
C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.c1cc2ccc3cccnc3c2nc1.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0316886541d9435489859c2ad7edc863
ord-50d901d10c4c44ac975534ef406fd151
C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1
[CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]...
C=Cc1ccccc1.Ic1ccccc1
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
CCN(CC)CC
O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C
CN(C)C=O
Aromatic Heterocycle Formation
Heck terminal vinyl
87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2
b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744
C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1
I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[...
null
[]
85
CELSIUS
16
HOUR
Environment: GLOVE_BOX Environment details: nitrogen atmosphere
null
null
Aromatic halide.Vinyl
Ether.Ether.Ether.Vinyl
c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
I-
CCN(CC)CC.O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C.CN(C)C=O
85
16
C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-ec80d4da92b544d0b0bc8fcb87523153
COc1cccc(C2(O)CCCCC2CN(C)C)c1.O>>COc1cccc(C2(O)CCCCC2CN(C)C)c1.COc1cccc(C2(O)CCCCC2C[N+](C)(C)[O-])c1
O.CN(C)CC1CCCCC1(C2=CC=CC(=C2)OC)O.Cl>>C[N+](C)(CC1CCCCC1(C2=CC(=CC=C2)OC)O)[O-].CN(C)CC1CCCCC1(C2=CC=CC(=C2)OC)O
[CH3:1][N:16]([CH3:19])[CH2:34][CH:33]1[C:27]([c:26]2[cH:25][cH:24][cH:23][c:22]([O:21][CH3:20])[cH:39]2)([OH:28])[CH2:29][CH2:30][CH2:31][CH2:32]1.[OH2:2]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8]2([OH:9])[CH2:10][CH2:11][CH2:12][CH2:13][CH:14]2[CH2:15][N:16]([CH3:17])[CH3:18])[cH:19]1.[CH3:20][O:21][c:22]1[cH:...
COc1cccc(C2(O)CCCCC2CN(C)C)c1.O
COc1cccc(C2(O)CCCCC2CN(C)C)c1.COc1cccc(C2(O)CCCCC2C[N+](C)(C)[O-])c1
null
null
null
Aromatic Heterocycle Formation
OtherReaction
55a822aad557c6248fe3a9094ee2664e11170115da4a42128399e6bbf97f7c01
3740eac2467e541a1875291f73ec0bdbfc11867866acb3d971e1a4e8b1357211
c1ccc(C2CCCCC2)cc1.c1ccc(C2CCCCC2)cc1
[C:1]-[C:2](-[CH2;D2;+0:3]-[N;H0;D3;+0:4](-[CH3;D1;+0:5])-[CH3;D1;+0:6])-[C:7].[OH2;D0;+0:8]>>[C;D1;H3:9]-[N;H0;D3;+0:4](-[C;D1;H3:10])-[C:11]-[C:12]-[C:13]-[c:14](:[c:15]):[cH;D2;+0:5]:[c:16](-[O;H0;D2;+0:8]-[CH3;D1;+0:6]):[c:17].[C:1]-[C:2](-[CH2;D2;+0:3]-[#7;+:18](-[C;D1;H3:19])(-[C;D1;H3:20])-[O;-;D1;H0:21])-[C:7]
null
[]
null
null
null
null
First, tramadol N-oxide was prepared as set forth hereinafter. Tramadol hydrochloride (0.5 mol) was converted to its free base in basified water (pH>9) and then extracted with ether. The ether was evaporated to yield the crystalline hydrate of tramadol. The solid was then heated with steam under a high vacuum to remove...
10.6084/m9.figshare.5104873.v1
null
Tertiary amine
Ether.Tertiary alcohol.Tertiary amine
null
c1ccccc1.C1CCCCC1
c1ccccc1.C1CCCCC1.c1ccccc1.C1CCCCC1
Other
null
null
null
COc1cccc(C2(O)CCCCC2CN(C)C)c1.O>>COc1cccc(C2(O)CCCCC2CN(C)C)c1.COc1cccc(C2(O)CCCCC2C[N+](C)(C)[O-])c1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-3d2de9dc77a241a391535aaa38779401
COc1cccc([C@]2(O)CCCC[C@H]2CN(C)C)c1>>CN(C)C[C@H]1CCCC[C@]1(O)c1cccc(O)c1
CN(C)C[C@@H]1CCCC[C@]1(C2=CC(=CC=C2)OC)O.[H-].[K+].C1(=CC=CC=C1)S>>CN(C)C[C@H]1CCCC[C@@]1(C=2C=CC=C(C2)O)O
C[O:17][c:16]1[cH:15][cH:14][cH:13][c:12]([C@@:10]2([OH:11])[C@H:5]([CH2:4][N:2]([CH3:1])[CH3:3])[CH2:6][CH2:7][CH2:8][CH2:9]2)[cH:18]1>>[CH3:1][N:2]([CH3:3])[CH2:4][C@H:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C@:10]1([OH:11])[c:12]1[cH:13][cH:14][cH:15][c:16]([OH:17])[cH:18]1
COc1cccc([C@]2(O)CCCC[C@H]2CN(C)C)c1
CN(C)C[C@H]1CCCC[C@]1(O)c1cccc(O)c1
null
null
C(COCCO)O
Deprotection
Cleavage of methoxy ethers to alcohols
c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5
26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4
c1ccc(C2CCCCC2)cc1
C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4]
null
[]
null
null
null
null
First, O-desmethyl tramadol was prepared as set forth hereinafter. Diethylene glycol (125 mL) was added with cooling to potassium hydride (9.5 g) with the temperature being maintained at <50° C. To the solution was added thiophenol (10 mL) dissolved in diethylene glycol (25 mL), and then (−)-tramadol as the free base (...
10.6084/m9.figshare.5104873.v1
null
Ether
Aromatic alcohol
null
null
C1CCCCC1.c1ccccc1
Other
C(COCCO)O
null
null
COc1cccc([C@]2(O)CCCC[C@H]2CN(C)C)c1>C(COCCO)O>CN(C)C[C@H]1CCCC[C@]1(O)c1cccc(O)c1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-74561ba7ee694134bb00b8692de7b1b8
COc1cccc([C@@]2(O)CCCC[C@@H]2CN(C)C)c1>>CN(C)C[C@H]1CCCC[C@]1(O)c1cccc(O)c1
CN(C)C[C@H]1CCCC[C@@]1(C2=CC(=CC=C2)OC)O.CN(C)C[C@@H]1CCCC[C@]1(C2=CC(=CC=C2)OC)O>>CN(C)C[C@H]1CCCC[C@@]1(C=2C=CC=C(C2)O)O
C[O:17][c:16]1[cH:15][cH:14][cH:13][c:12]([C@:10]2([OH:11])[C@@H:5]([CH2:4][N:2]([CH3:1])[CH3:3])[CH2:6][CH2:7][CH2:8][CH2:9]2)[cH:18]1>>[CH3:1][N:2]([CH3:3])[CH2:4][C@H:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C@:10]1([OH:11])[c:12]1[cH:13][cH:14][cH:15][c:16]([OH:17])[cH:18]1
COc1cccc([C@@]2(O)CCCC[C@@H]2CN(C)C)c1
CN(C)C[C@H]1CCCC[C@]1(O)c1cccc(O)c1
null
null
CCO
Deprotection
Cleavage of methoxy ethers to alcohols
c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5
26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4
c1ccc(C2CCCCC2)cc1
C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4]
null
[]
null
null
null
null
To prepare the (+) enantiomer of the title compound, the reaction was run under the same conditions except that (+)-tramadol as the free base was used instead of the (−)-tramadol to yield 2.8 g of the (+) enantiomer of O-desmethyl tramadol (mp. 242°-3° C.) [α]D25=+32.2 (C=1, EtOH). Conditions: See reaction.notes.proced...
10.6084/m9.figshare.5104873.v1
null
Ether
Aromatic alcohol
null
null
C1CCCCC1.c1ccccc1
Other
CCO
null
null
COc1cccc([C@@]2(O)CCCC[C@@H]2CN(C)C)c1>CCO>CN(C)C[C@H]1CCCC[C@]1(O)c1cccc(O)c1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-4dd019e84355481ab7d6cab2142e4e33
CC(=O)O.CC(=O)OC(C)=O>>CC(=O)CC(=O)CC(=O)O
IC1=C(C(=C(C(=C1C)I)C)I)C.[Mn](=O)(=O)(=O)[O-].[K+].C(C)(=O)OC(C)=O.C(C)(=O)O.S(O)(O)(=O)=O>>CC(=O)CC(=O)CC(=O)O
[CH3:7][C:8](=[O:9])[OH:10].O([C:2]([CH3:1])=[O:3])[C:5]([CH3:4])=[O:6]>>[CH3:1][C:2](=[O:3])[CH2:4][C:5](=[O:6])[CH2:7][C:8](=[O:9])[OH:10]
CC(=O)O.CC(=O)OC(C)=O
CC(=O)CC(=O)CC(=O)O
null
null
null
C-C Coupling
OtherReaction
cf430baac3f766747c207639460decd809b6eb94c446cbfb7c2a264f85a8826d
cc4176ffd341335b205c3971b5efed61e7c5e9c91d0e5c98056978e074809377
null
[C;D1;H3:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-O-[C;H0;D3;+0:4](-[CH3;D1;+0:5])=[O;D1;H0:6].[CH3;D1;+0:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]>>[C;D1;H3:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[CH2;D2;+0:5]-[C;H0;D3;+0:4](=[O;D1;H0:6])-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]
35
[{"value": 35.0, "product": "CC(=O)CC(=O)CC(=O)O", "details": "PERCENTYIELD", "is_desired": false}]
null
null
null
null
Triiodomesitylene is converted under acetylating conditions in an oxidation reaction with potassium permanganate/acetic anhydride/acetic acid/sulfuric acid into triacetate (yield: 35%). The triacetate is isolated and saponified with potassium carbonate in methanol to tris alcohol (yield: 94%). The tris alcohol is then ...
10.6084/m9.figshare.5104873.v1
null
Anhydride
Ketone.Ketone
null
null
null
HO-
null
null
null
CC(=O)O.CC(=O)OC(C)=O>>CC(=O)CC(=O)CC(=O)O
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-6d6b4bc9fa3d40c9a1bb0732d741e517
CCI.CCI.Clc1ccc(C2(CN3CCCC3)CC2)cc1>>CC[N+]1(CC2(c3ccc(Cl)cc3)CC2)CCCC1.[I-]
ClC1=CC=C(C=C1)C1(CC1)CN1CCCC1.C(C)I.C(C)I.C(C)I>>[I-].ClC1=CC=C(C=C1)C1(CC1)C[N+]1(CCCC1)CC
CC[I:19].I[CH2:2][CH3:1].[N:3]1([CH2:4][C:5]2([c:6]3[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]3)[CH2:13][CH2:14]2)[CH2:15][CH2:16][CH2:17][CH2:18]1>>[CH3:1][CH2:2][N+:3]1([CH2:4][C:5]2([c:6]3[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]3)[CH2:13][CH2:14]2)[CH2:15][CH2:16][CH2:17][CH2:18]1.[I-:19]
CCI.CCI.Clc1ccc(C2(CN3CCCC3)CC2)cc1
CC[N+]1(CC2(c3ccc(Cl)cc3)CC2)CCCC1.[I-]
null
null
CO
Heteroatom Alkylation and Arylation
OtherReaction
2de856e2b4c10600b4dc7dd3b4f6221d198bde47cfb63ff7b7b7838efe60f985
55b5813305c1bcf759cbb20a320edf0cdab0cb7397777aced662172da8c4c46e
c1ccc(C2(C[NH+]3CCCC3)CC2)cc1
C-C-[I;H0;D1;+0:1].I-[CH2;D2;+0:2]-[C;D1;H3:3].[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C:7]-[C:8]-[C:9]-[C:10]-1>>[C:4]-[C:5]-[N+;H0;D4:6]1(-[CH2;D2;+0:2]-[C;D1;H3:3])-[C:7]-[C:8]-[C:9]-[C:10]-1.[I-;H0;D0:1]
93
[{"value": 93.0, "product": "[I-].ClC1=CC=C(C=C1)C1(CC1)C[N+]1(CCCC1)CC", "details": "PERCENTYIELD", "is_desired": false}]
null
null
72
HOUR
1-[1-(4-chloro-phenyl)-cyclopropylmethyl]-1-ethyl-pyrrolidinium iodide is prepared from the reaction of the parent amine 1-[1-(4-chloro-phenyl)-cyclopropylmethyl]-pyrrolidine with ethyl iodide. A 100 gm (0.42 mole) of the amine, 1-[1-(4-chloro-phenyl)-cyclopropylmethyl]-pyrrolidine, is dissolved in 1000 ml anhydrous me...
10.6084/m9.figshare.5104873.v1
null
Primary halide.Primary halide.Tertiary amine
null
C1CC[NH]C1
C1CC[NH+]C1
c1ccccc1.C1CC1.C1CC[NH+]C1
HI
CO
null
72
CCI.CCI.Clc1ccc(C2(CN3CCCC3)CC2)cc1>CO>CC[N+]1(CC2(c3ccc(Cl)cc3)CC2)CCCC1.[I-]
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-3bcb5549129f4f7781a17099a365cfae
O>>[OH-]
[I-].ClC1=CC=C(C=C1)C1(CC1)C[N+]1(CCCC1)CC.O>>[OH-].ClC1=CC=C(C=C1)C1(CC1)C[N+]1(CCCC1)CC
[OH2:19]>>[OH-:19]
O
[OH-]
null
null
null
Oxidation
OtherReaction
8411f9fce1f185c5c08a89a741e7494817f2d5e55ac6ad2b663e4ffb9ef8fbab
82a3692de44364afcfd8cc4460435180e0752c31812bf6008d75e02664a32947
null
[OH2;D0;+0:1]>>[OH-;D0:1]
96
[{"value": 96.0, "product": "[OH-].ClC1=CC=C(C=C1)C1(CC1)C[N+]1(CCCC1)CC", "details": "PERCENTYIELD", "is_desired": false}]
null
null
8
HOUR
The hydroxide form of 1-[1-(4-chloro-phenyl)-cyclopropyhnethyl]-1-ethyl-pyrrolidinium cation is obtained by an ion exchange treatment of the iodide salt with Ion-Exchange Resin-OH (BIO RAD® AH1-X8). In a 1-liter volume plastic bottle, 100 gm (255 mmol) of 1-[1-(4-chloro-phenyl)-cyclopropylmethyl]-1-ethyl-pyrrolidinium ...
10.6084/m9.figshare.5104873.v1
null
null
null
null
null
null
null
null
null
8
O>>[OH-]
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-dbd5b85fe1244ba694c10d25e70831d6
O=C(O)CC(O)(CC(=O)O)C(=O)O>>O.O=C(O)CC(O)(CC(=O)O)C(=O)O
C(CC(O)(C(=O)O)CC(=O)O)(=O)O>>O.C(CC(O)(C(=O)O)CC(=O)O)(=O)O
[O:1]=[C:9]([CH2:8][C:6]([CH2:5][C:3](=[O:2])[OH:4])([OH:7])[C:12](=[O:13])[OH:14])[OH:11]>>[OH2:1].[O:2]=[C:3]([OH:4])[CH2:5][C:6]([OH:7])([CH2:8][C:9](=[O:10])[OH:11])[C:12](=[O:13])[OH:14]
O=C(O)CC(O)(CC(=O)O)C(=O)O
O.O=C(O)CC(O)(CC(=O)O)C(=O)O
null
null
O
Functional Group Addition
OtherReaction
a26402a48eb822fc9193bf4ff99f1654c7ad83d26f9e5a9ea81c3a74cbd7d178
5b38f984b30dc8ba79a347cf52032250fd6e2fc536334a7105c3453f18979742
null
[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[C:4]-[C:5]-[C;H0;D3;+0:6](-[O;D1;H1:7])=[O;H0;D1;+0:8]>>[O;D1;H0:9]=[C;H0;D3;+0:6](-[O;D1;H1:7])-[C:5]-[C:4]-[C:2](=[O;D1;H0:1])-[O;D1;H1:3].[OH2;D0;+0:8]
null
[]
80
CELSIUS
null
null
Further, citric acid (approximately 30 g), which enables certain catalytic reactions, is stirred with silicon (approximately 30 g) simultaneously into water, and then heated at 80° C. for approximately one hour to produce citric acid water. Conditions: See reaction.notes.procedure_details.
10.6084/m9.figshare.5104873.v1
null
Carboxylic acid
Carboxylic acid
null
null
null
Other
O
80
null
O=C(O)CC(O)(CC(=O)O)C(=O)O>O>O.O=C(O)CC(O)(CC(=O)O)C(=O)O
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-b089b4cdb71a4c93ac0c6b2f9f6f79ef
FC(F)=C(F)Cl.O=C(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)F>>O=C(F)C(F)(F)C(F)(F)F
C(F)(F)(F)C(F)(F)C(=O)OC(F)(F)C(F)(F)C(F)(F)F.ClC(=C(F)F)F>>C(F)(F)(F)C(F)(F)C(=O)F
FC(F)=C(Cl)[F:3].FC(F)(F)C(F)(F)C(F)(F)O[C:2](=[O:1])[C:4]([F:5])([F:6])[C:7]([F:8])([F:9])[F:10]>>[O:1]=[C:2]([F:3])[C:4]([F:5])([F:6])[C:7]([F:8])([F:9])[F:10]
FC(F)=C(F)Cl.O=C(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)F
O=C(F)C(F)(F)C(F)(F)F
null
[Ni]
O
Functional Group Interconversion
OtherReaction
e7d1dbbbb4d574414c2480057181d1d42b3cbecb2083e12a954b5370242ede21
0dc4081f189cecb5476cac09bbbb6bfb9a07a80ade96d888e6adcc5fba79c54e
null
Cl-C(-[F;H0;D1;+0:1])=C(-F)-F.F-C(-F)(-F)-C(-F)(-F)-C(-F)(-F)-O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[F;D1;H0:10]>>[F;D1;H0:8]-[C:7](-[F;D1;H0:9])(-[F;D1;H0:10])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[C;H0;D3;+0:2](-[F;H0;D1;+0:1])=[O;D1;H0:3]
90
[{"value": 90.0, "product": "C(F)(F)(F)C(F)(F)C(=O)F", "details": "PERCENTYIELD", "is_desired": false}]
200
CELSIUS
null
null
CF3CF2COOCF2CF2CF3 (20 g) obtained in Example 5 and chlorotrifluoroethylene oligomer (120 g) were charged into a 200 ml autoclave made of nickel and equipped with a reflux condenser and heated to 200° C. The reflux condenser was cooled by circulating cooling water, and when the pressure became at least 0.1 MPa, the gas...
10.6084/m9.figshare.5104873.v1
null
Trifluoro group.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Alkenyl halide.Alkenyl halide.Alkenyl halide.Alkenyl halide.Ester
Acyl halide
null
null
null
Other
[Ni].O
200
null
FC(F)=C(F)Cl.O=C(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)F>[Ni].O>O=C(F)C(F)(F)C(F)(F)F
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-dbaa5083ab4f45b68a157d163cac29d9
CCCCCCCCCCO>>CCCCCCCCCC[O-]
C(CCCCCCCCC)O.C[O-].[Na+]>>CCCCCCCCCC[O-].[Na+]
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O-:11]
CCCCCCCCCCO
CCCCCCCCCC[O-]
null
null
CO
Oxidation
OtherReaction
d20f19b0fec5d4c5c8a0f8d7581d729ff925d8dfa06d8f94c1c8e3f60d67d89b
2fe32d9d921345d69363047716a847fef3b1772fc7f02a5de9c3282e3e55d364
null
[C:1]-[C:2]-[OH;D1;+0:3]>>[C:1]-[C:2]-[O-;H0;D1:3]
null
[]
null
null
null
null
Into a 500 ml eggplant type flask, 1-decanol (180 g) and a methanol solution of sodium methylate (28%) were charged, stirred and heated under reduced pressure to distill off methanol. By GC, it was confirmed that no methanol remained in the reaction solution. Into a 1 l four-necked flask, N,N-dimethylformamide (150 ml)...
10.6084/m9.figshare.5104873.v1
null
Primary alcohol
null
null
null
null
null
CO
null
null
CCCCCCCCCCO>CO>CCCCCCCCCC[O-]
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-c7929215a1044905b53af2ac9d1a111e
O=C(OC(F)(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F.[F-]>>O=C(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F
C(F)(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC(F)(C(F)(F)F)C(F)(F)OC(=O)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C(F)(F)F.[F-].[Na+]>>C(F)(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC(F)(C(F)(F)F)C(=O)F
FC(F)(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)[C:16]([F:17])([F:18])[C:19]([F:20])([F:21])[C:22]([F:23])([F:24])[C:25]([F:26])([F:27])[C:28]([F:29])([F:30])[C:31]([F:32])([F:33])[C:34]([F:35])([F:36])[F:37])C(F)(F)O[C:2](=[O:1])[C:4]([F:5])([O:6][C:7]([F:8])([F:9])[C:10]([F:11])([F:12])[C:13](F)([F:14])[F:15])[C:38]([F:39])([F:40...
O=C(OC(F)(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F.[F-]
O=C(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F
null
null
null
Functional Group Interconversion
OtherReaction
175f10fd8f6b717d4a7692899b5a20ac7cb402774ca27f65733525abd66f906d
9ed502372e4f910107dee191d1ea1223d6ecc03989a8579a285d97126bab7a62
null
F-C(-F)(-F)-C(-F)(-O-C(-F)(-F)-C(-F)(-F)-C(-F)(-F)-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[F;D1;H0:3])-[C:4](-[C:5])(-[F;D1;H0:6])-[F;D1;H0:7])-C(-F)(-F)-O-[C;H0;D3;+0:8](=[O;D1;H0:9])-[C:10](-[F;D1;H0:11])(-[#8:12]-[C:13]-[C:14](-[F;D1;H0:15])(-[F;D1;H0:16])-[C;H0;D4;+0:17](-F)(-[F;D1;H0:18])-[F;D1;H0:19])-[C:20](-[F;D1;H0:21]...
63.8
[{"value": 63.8, "product": "C(F)(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC(F)(C(F)(F)F)C(=O)F", "details": "PERCENTYIELD", "is_desired": false}]
150
CELSIUS
null
null
CF3(CF2)9OCF(CF3)CF2OCOCF(CF3)OCF2CF2CF3 (2.0 g) obtained in Example 23 was charged into a flask together with a NaF powder (0.05 g) and heated at 150° C. for 24 hours in an oil bath with vigorous stirring. At an upper part of the flask, a reflux condenser adjusted to a temperature of 20° C., was installed. After cooli...
10.6084/m9.figshare.5104873.v1
null
Trifluoro group.Trifluoro group.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Ester.Ether
Acyl halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide
null
null
null
Other
null
150
null
O=C(OC(F)(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F.[F-]>>O=C(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-da416716b18045318a79e460f3c3b0be
C=CCCO.CC(Cl)C(=O)O>>C=CCCOC(=O)C(C)Cl
C([O-])([O-])=O.[Na+].[Na+].CC(Cl)C(=O)O.C=CCCO.S(O)(O)(=O)=O>>CC(Cl)C(=O)OCCC=C
[CH2:1]=[CH:2][CH2:3][CH2:4][OH:5].O[C:6](=[O:7])[CH:8]([CH3:9])[Cl:10]>>[CH2:1]=[CH:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[CH:8]([CH3:9])[Cl:10]
C=CCCO.CC(Cl)C(=O)O
C=CCCOC(=O)C(C)Cl
null
null
C(C)(C)(C)OC.O
Protection
Esterification of Carboxylic Acids
070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e
0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690
null
O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[Cl;D1;H0:5].[C;D1;H2:6]=[C:7]-[C:8]-[C:9]-[OH;D1;+0:10]>>[C;D1;H2:6]=[C:7]-[C:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[Cl;D1;H0:5]
null
[]
null
null
10
MINUTE
CH3CHClCOOH (50 g) and CH2═CHCH2CH2OH (75 ml) were put into a flask, and 10 ml of concentrated sulfuric acid was added dropwise, followed by stirring at room temperature for 10 minutes. The reaction solution was poured into 250 ml of a saturated sodium carbonate aqueous solution. 150 ml of water and 150 ml of t-butylme...
10.6084/m9.figshare.5104873.v1
null
Carboxylic acid.Primary alcohol
Ester
null
null
null
HO-
C(C)(C)(C)OC.O
null
0.166667
C=CCCO.CC(Cl)C(=O)O>C(C)(C)(C)OC.O>C=CCCOC(=O)C(C)Cl
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-6ba226ea566049a98b1b22bf00db0771
O=C(OC(F)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F.[F-]>>O=C(F)C(F)(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)F
C(F)(F)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)OC(=O)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C(F)(F)F.[F-].[Na+]>>C(F)(F)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)(F)C(=O)F
FC(F)(F)C(F)(F)C(F)(F)O[C:4]([C:2](OC(F)(F)C(F)(C(F)(F)[O:10][C:11]([F:12])([F:13])[C:14]([F:15])([F:16])[C:17]([F:18])([F:19])[F:20])[F:6])=[O:1])([F:5])[C:7](F)([F:8])[F:9].[F-:3]>>[O:1]=[C:2]([F:3])[C:4]([F:5])([F:6])[C:7]([F:8])([F:9])[O:10][C:11]([F:12])([F:13])[C:14]([F:15])([F:16])[C:17]([F:18])([F:19])[F:20]
O=C(OC(F)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F.[F-]
O=C(F)C(F)(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)F
null
null
null
Functional Group Interconversion
OtherReaction
7d2bcdda8c5e449bcc2582b9f05aa74ecb8468648948d439fd89b09ff6c701f3
50f0c3225cc15853e34d417f6bda24c562484b0a1f68ac283d9c5d60f3f8f705
null
F-C(-F)(-F)-C(-F)(-F)-C(-F)(-F)-O-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[C;H0;D3;+0:3](=[O;D1;H0:4])-O-C(-F)(-F)-C(-F)(-[F;H0;D1;+0:5])-C(-F)(-F)-[O;H0;D2;+0:6]-[C:7](-[C:8])(-[F;D1;H0:9])-[F;D1;H0:10])-[C;H0;D4;+0:11](-F)(-[F;D1;H0:12])-[F;D1;H0:13].[F-;H0;D0:14]>>[C:8]-[C:7](-[F;D1;H0:9])(-[F;D1;H0:10])-[O;H0;D2;+0:6]-[C;H0;...
57
[{"value": 57.0, "product": "C(F)(F)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)(F)C(=O)F", "details": "PERCENTYIELD", "is_desired": false}]
120
CELSIUS
null
null
CF3CF2CF2OCF2CF2CF2OCOCF(CF3)OCF2CF2CF3 (0.8 g) obtained in Example 42 was charged into a flask together with a NaF powder (0.01 g) and heated at 120° C. for 10 hours in an oil bath with vigorous stirring. At an upper portion of the flask, a reflux condenser adjusted to a temperature of 20° C. was installed. After cool...
10.6084/m9.figshare.5104873.v1
null
Trifluoro group.Trifluoro group.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Ester.Ether.Ether
Acyl halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Ether
null
null
null
Other
null
120
null
O=C(OC(F)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F.[F-]>>O=C(F)C(F)(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)F
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-77814c110edc4862859dc162723022c7
Ic1ccccc1.c1ccc(Nc2ccc(Nc3ccccc3)cc2)cc1>>c1ccc(N(c2ccccc2)c2ccc(N(c3ccccc3)c3ccccc3)cc2)cc1
C=1C=CC(=CC1)NC=2C=CC(=CC2)NC=3C=CC=CC3.IC1=CC=CC=C1.C(=O)([O-])[O-].[K+].[K+].II>>C1(=CC=CC=C1)N(C1=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1
I[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[cH:1]1[cH:2][cH:3][c:23]([NH:16][c:15]2[cH:14][cH:13][c:12]([NH:5][c:6]3[cH:7][cH:8][cH:9][cH:10][cH:11]3)[cH:30][cH:29]2)[cH:31][cH:32]1>>[cH:1]1[cH:2][cH:3][c:4]([N:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]2[cH:13][cH:14][c:15]([N:16]([c:17]3[cH:18][cH:19][cH:20][...
Ic1ccccc1.c1ccc(Nc2ccc(Nc3ccccc3)cc2)cc1
c1ccc(N(c2ccccc2)c2ccc(N(c3ccccc3)c3ccccc3)cc2)cc1
null
[Cu]
[N+](=O)([O-])C1=CC=CC=C1
Aromatic Heterocycle Formation
OtherReaction
bfe0f0bca10882fba93b8648a6cc0fbee4a79013a43a8d5cad4326609b6d2b06
119e8273291698aaeabc2f90d6b62f36f5919a412042c0960daa9a481ba209b1
c1ccc(N(c2ccccc2)c2ccc(N(c3ccccc3)c3ccccc3)cc2)cc1
I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[c:6]:[c:7](-[NH;D2;+0:8]-[c:9]1:[c:10]:[c:11]:[c:12](-[NH;D2;+0:13]-[c;H0;D3;+0:14]2:[cH;D2;+0:15]:[c:16]:[c:17]:[c:18]:[cH;D2;+0:19]:2):[c:20]:[c:21]:1):[c:22]>>[c:6]:[c:7](-[N;H0;D3;+0:8](-[c:9]1:[c:10]:[c:11]:[c:12](-[N;H0;D3;+0:13](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5...
111.3
[{"value": 111.3, "product": "C1(=CC=CC=C1)N(C1=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}]
null
null
null
null
41.4 g of N,N′-diphenyl-p-phenylenediamine, 66 g of iodobenzene, 100 ml of nitrobenzene, 45 g of K2CO3, 10.8 g of copper powder, and I2 (trace) were put in a four-neck flask of 300-milliliter volume, and were refluxed gently over 24 hours by stirring the same while removing generated water by reflux. Subsequently, stea...
10.6084/m9.figshare.5104873.v1
null
Aromatic halide.Secondary amine.Secondary amine
Tertiary amine.Tertiary amine
c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
I-
[Cu].[N+](=O)([O-])C1=CC=CC=C1
null
null
Ic1ccccc1.c1ccc(Nc2ccc(Nc3ccccc3)cc2)cc1>[Cu].[N+](=O)([O-])C1=CC=CC=C1>c1ccc(N(c2ccccc2)c2ccc(N(c3ccccc3)c3ccccc3)cc2)cc1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-747a39fbf3734e7585c10393e8a4c1b7
C1=Cc2cccc3cccc(c23)C1.c1ccncc1>>c1cc2ccc3c4ccc5cccc6ccc(c7ccc(c1)c2c37)c4c56
C1C=CC2=CC=CC3=C2C1=CC=C3.N1=CC=CC=C1>>C1=CC2=C3C(=C1)C=CC4=C3C(=C5C=CC6=C7C5=C4C=CC7=CC=C6)C=C2
[cH:11]1[cH:12][cH:13][c:14]2[cH:15][cH:16][cH:17][c:18]3[c:24]2[c:23]1[CH:21]=[CH:20][CH2:19]3.n1[cH:1][cH:26][cH:10][cH:9][cH:8]1>>[cH:1]1[cH:2][c:3]2[cH:4][cH:5][c:6]3[c:7]4[cH:8][cH:9][c:10]5[cH:11][cH:12][cH:13][c:14]6[cH:15][cH:16][c:17]([c:18]7[cH:19][cH:20][c:21]([cH:22]1)[c:23]2[c:24]37)[c:25]4[c:26]56
C1=Cc2cccc3cccc(c23)C1.c1ccncc1
c1cc2ccc3c4ccc5cccc6ccc(c7ccc(c1)c2c37)c4c56
null
[Zn]
C(C)(=O)O
Miscellaneous
OtherReaction
b0a674788f6bc4d2dca980a154c4ed0d133503be20e3b677a36b32a852a9a772
56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd
c1cc2ccc3c4ccc5cccc6ccc(c7ccc(c1)c2c37)c4c56
[CH2;D2;+0:1]1-[CH;D2;+0:2]=[CH;D2;+0:3]-[c;H0;D3;+0:4]2:[cH;D2;+0:5]:[c:6]:[c:7]:[c;H0;D3;+0:8]3:[c:9]:[c:10]:[cH;D2;+0:11]:[c:12]-1:[c;H0;D3;+0:13]:3:2.[c:14]1:[cH;D2;+0:15]:[cH;D2;+0:16]:[cH;D2;+0:17]:n:[cH;D2;+0:18]:1>>[c:6]1:[c:7]:[c;H0;D3;+0:8]2:[c:9]:[c:10]:[c;H0;D3;+0:11]3:[c:12]4:[cH;D2;+0:1]:[cH;D2;+0:2]:[c;H...
null
[]
null
null
null
null
With reference to the following scheme, perinaphthene and zinc powder were added to pyridine (I in the following synthesis scheme), 50 ml of 80% acetic acid was added dropwise thereto with stirring under reflux in nitrogen flow over five hours, the resulting precipitate (II in the following synthesis scheme I) was filt...
10.6084/m9.figshare.5104873.v1
null
null
null
C1=Cc2cccc3cccc(c23)C1.c1ccncc1
c1cc2ccc3c4ccc5cccc6ccc(c7ccc(c1)c2c37)c4c56
c1cc2ccc3c4ccc5cccc6ccc(c7ccc(c1)c2c37)c4c56
null
[Zn].C(C)(=O)O
null
null
C1=Cc2cccc3cccc(c23)C1.c1ccncc1>[Zn].C(C)(=O)O>c1cc2ccc3c4ccc5cccc6ccc(c7ccc(c1)c2c37)c4c56
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-625c6e1d30dd4d0a9f0e4279bcd0f5ff
CCI.c1ccc2c(c1)Nc1ccccc1S2>>CCN1c2ccccc2Sc2ccccc21
C1=CC=CC=2SC3=CC=CC=C3NC12.ICC.[OH-].[K+]>>C(C)N1C2=CC=CC=C2SC=2C=CC=CC12
I[CH2:2][CH3:1].[NH:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[S:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21>>[CH3:1][CH2:2][N:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[S:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21
CCI.c1ccc2c(c1)Nc1ccccc1S2
CCN1c2ccccc2Sc2ccccc21
null
S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC
C1(=CC=CC=C1)C
Heteroatom Alkylation and Arylation
N-alkylation of secondary amines with alkyl halides
336cc78323abd7b2f923e51f272cac68a761bcd91fabccedc45cab957f74be2a
523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0
c1ccc2c(c1)Nc1ccccc1S2
I-[CH2;D2;+0:1]-[C;D1;H3:2].[c:3]:[c:4]1:[c:5]-[#16:6]-[c:7]:[c:8](:[c:9])-[NH;D2;+0:10]-1>>[C;D1;H3:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[c:4](:[c:3]):[c:5]-[#16:6]-[c:7]:[c:8]-1:[c:9]
null
[]
null
null
null
null
A mixture of 10 g (0.05 mol) of phenothiazine, 11.7 g (0.075 mol) of iodoethane, 4.2 g (0.075 mol) of potassium hydroxide and 0.25 g of tetra-n-butylammonium hydrogen sulfate in 200 ml of dry toluene was refluxed for 24 hours. After cooling, the reaction mixture was filtered, and the solvent was evaporated. The product...
10.6084/m9.figshare.5104873.v1
null
Primary halide.Secondary amine
Tertiary amine
c1ccc2c(c1)Nc1ccccc1S2
c1ccc2c(c1)[NH]c1ccccc1S2
c1ccc2c(c1)[NH]c1ccccc1S2
HI
S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)C
null
null
CCI.c1ccc2c(c1)Nc1ccccc1S2>S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)C>CCN1c2ccccc2Sc2ccccc21
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-aab5b1b567764967a3b9eb9b16000b36
CCN1c2ccccc2Sc2ccccc21.CN(C)C=O>>CCN1c2ccccc2Sc2cc(C=O)ccc21
[OH-].[K+].P(=O)(Cl)(Cl)Cl.CN(C=O)C.C(C)N1C2=CC=CC=C2SC=2C=CC=CC12.CN(C=O)C>>C(C)N1C2=CC=CC=C2SC=2C=C(C=CC12)C=O
[CH3:1][CH2:2][N:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[S:10][c:11]2[cH:12][cH:13][cH:16][cH:17][c:18]21.CN(C)[CH:14]=[O:15]>>[CH3:1][CH2:2][N:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[S:10][c:11]2[cH:12][c:13]([CH:14]=[O:15])[cH:16][cH:17][c:18]21
CCN1c2ccccc2Sc2ccccc21.CN(C)C=O
CCN1c2ccccc2Sc2cc(C=O)ccc21
null
null
null
C-C Coupling
OtherReaction
cb71a0376b4208dbd8e7332a85c98656a16f85fb885d0265492cd365290cd221
f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7
c1ccc2c(c1)Nc1ccccc1S2
C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[#16:3]-[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[#16:3]-[c:4]:[c:5]:[c;H0;D3;+0:6](-[CH;D2;+0:1]=[O;D1;H0:2]):[c:7]:[c:8]
null
[]
null
null
null
null
Phosphorus oxychloride (POCl3,3.7 ml, 0.04 mol) was added dropwise to 4.4 ml (0.06 mol) of dry dimethylformamide (DMF) at 0° C. under a nitrogen atmosphere. This solution was warmed up slowly to room temperature. Then, a solution of 5 g (0.02 mol) of 10-ethylphenothiazine in dry DMF was added dropwise. The reaction mix...
10.6084/m9.figshare.5104873.v1
null
Tertiary amide
Aldehyde
c1ccc2c(c1)[NH]c1ccccc1S2
c1ccc2c(c1)[NH]c1ccccc1S2
c1ccc2c(c1)[NH]c1ccccc1S2
Other
null
null
null
CCN1c2ccccc2Sc2ccccc21.CN(C)C=O>>CCN1c2ccccc2Sc2cc(C=O)ccc21
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-fb80e6a8fc8140659b99210a7b1dab94
CCN1c2ccccc2Sc2cc(C=O)ccc21.NNc1ccccc1>>CCN1c2ccccc2Sc2cc(C=NNc3ccccc3)ccc21
C(C)N1C2=CC=CC=C2SC=2C=C(C=CC12)C=O.C1(=CC=CC=C1)NN>>C1(=CC=CC=C1)NN=CC=1C=CC=2N(C3=CC=CC=C3SC2C1)CC
O=[CH:14][c:13]1[cH:12][c:11]2[c:25]([cH:24][cH:23]1)[N:3]([CH2:2][CH3:1])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[S:10]2.[NH2:15][NH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][CH2:2][N:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[S:10][c:11]2[cH:12][c:13]([CH:14]=[N:15][NH:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH...
CCN1c2ccccc2Sc2cc(C=O)ccc21.NNc1ccccc1
CCN1c2ccccc2Sc2cc(C=NNc3ccccc3)ccc21
null
null
CO
Heteroatom Alkylation and Arylation
OtherReaction
c78be09cf200f3a07b02946ce0bbc22b647e9aaae7494d0480373904a4f330a9
c3cbc07b90655a7aa9777b584274a03a2ec0cff34c5b5edc214a16916fe29f1c
C(=NNc1ccccc1)c1ccc2c(c1)Sc1ccccc1N2
O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[#7:6]-[c:7]>>[c:3]:[c:2](-[CH;D2;+0:1]=[N;H0;D2;+0:5]-[#7:6]-[c:7]):[c:4]
null
[]
null
null
null
null
10-Ethylphenothiazine-3-carbaldehyde (3 g, 0.012 mol) was dissolved in 30 ml of methanol under mild heating. A solution of 1.9 g (0.018 mol) of N-phenylhydrazine in methanol was added to the cooled reaction mixture. Then, the reaction mixture was refluxed for 0.5 hour. The precipitated product was filtered, washed with...
10.6084/m9.figshare.5104873.v1
null
Hydrazine.Aldehyde
Hydrazone
null
null
c1ccc2c(c1)[NH]c1ccccc1S2.c1ccccc1
HO-
CO
null
null
CCN1c2ccccc2Sc2cc(C=O)ccc21.NNc1ccccc1>CO>CCN1c2ccccc2Sc2cc(C=NNc3ccccc3)ccc21
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-10cd9bcb707747a38156df7f0aa3849c
BrP(Br)Br.CC(C)(C)c1cc(C=Cc2cc(C=Cc3cc(C(C)(C)C)cc(C(C)(C)C)c3)cc(CO)c2)cc(C(C)(C)C)c1>>CC(C)(C)c1cc(C=Cc2cc(C=Cc3cc(C(C)(C)C)cc(C(C)(C)C)c3)cc(CBr)c2)cc(C(C)(C)C)c1
P(Br)(Br)Br.C(C)(C)(C)C=1C=C(C=CC=2C=C(CO)C=C(C2)C=CC2=CC(=CC(=C2)C(C)(C)C)C(C)(C)C)C=C(C1)C(C)(C)C.CC(C)O>>C(C)(C)(C)C=1C=C(C=CC=2C=C(CBr)C=C(C2)C=CC2=CC(=CC(=C2)C(C)(C)C)C(C)(C)C)C=C(C1)C(C)(C)C
BrP(Br)[Br:32].O[CH2:31][c:30]1[cH:29][c:12]([CH:13]=[CH:14][c:15]2[cH:16][c:17]([C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22][c:23]([C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28]2)[cH:11][c:10]([CH:9]=[CH:8][c:7]2[cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:40][c:35]([C:36]([CH3:37])([CH3:38])[CH3:39])[cH:34]2)[cH:33]1>>[C...
BrP(Br)Br.CC(C)(C)c1cc(C=Cc2cc(C=Cc3cc(C(C)(C)C)cc(C(C)(C)C)c3)cc(CO)c2)cc(C(C)(C)C)c1
CC(C)(C)c1cc(C=Cc2cc(C=Cc3cc(C(C)(C)C)cc(C(C)(C)C)c3)cc(CBr)c2)cc(C(C)(C)C)c1
null
null
ClCCl
Functional Group Interconversion
PBr3 and alcohol to alkyl bromide
bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071
cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf
C(=Cc1cccc(C=Cc2ccccc2)c1)c1ccccc1
Br-P(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]
85
[{"value": 85.0, "product": "C(C)(C)(C)C=1C=C(C=CC=2C=C(CBr)C=C(C2)C=CC2=CC(=CC(=C2)C(C)(C)C)C(C)(C)C)C=C(C1)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.5, "product": "C(C)(C)(C)C=1C=C(C=CC=2C=C(CBr)C=C(C2)C=CC2=CC(=CC(=C2)C(C)(C)C)C(C)(C)C)C=C(C1)C(C)(C)C", "details": "CALCULATEDPERCENTYIE...
null
null
3
HOUR
Phosphorus tribromide (2.8 cm3, 30 mmol) was added to a solution of 3,5-bis(3′,5′-di-tert-butylstyryl)benzyl alcohol (1.60 g, 3.0 mmol) in dichloromethane (50 cm3) and the mixture stirred at room temperature for 3 h. Propan-2-ol (14 cm3) was added slowly and the solvent was completely removed. The residue was purified ...
10.6084/m9.figshare.5104873.v1
null
Primary alcohol
Primary halide
null
null
c1ccccc1.c1ccccc1.c1ccccc1
HBr
ClCCl
null
3
BrP(Br)Br.CC(C)(C)c1cc(C=Cc2cc(C=Cc3cc(C(C)(C)C)cc(C(C)(C)C)c3)cc(CO)c2)cc(C(C)(C)C)c1>ClCCl>CC(C)(C)c1cc(C=Cc2cc(C=Cc3cc(C(C)(C)C)cc(C(C)(C)C)c3)cc(CBr)c2)cc(C(C)(C)C)c1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-ba5e0dbceb244edeabb972ef6039049c
CC(C)(C)c1cc(C=Cc2cc(C=O)cc(C=Cc3cc(C(C)(C)C)cc(C(C)(C)C)c3)c2)cc(C(C)(C)C)c1>>CC(C)(C)c1cc(C=Cc2cc(C=Cc3cc(C(C)(C)C)cc(C(C)(C)C)c3)cc(CO)c2)cc(C(C)(C)C)c1
C(C)(C)(C)C=1C=C(C=CC=2C=C(C=O)C=C(C2)C=CC2=CC(=CC(=C2)C(C)(C)C)C(C)(C)C)C=C(C1)C(C)(C)C.[BH4-].[Na+]>>C(C)(C)(C)C=1C=C(C=CC=2C=C(CO)C=C(C2)C=CC2=CC(=CC(=C2)C(C)(C)C)C(C)(C)C)C=C(C1)C(C)(C)C
[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([CH:8]=[CH:9][c:10]2[cH:11][c:12]([CH:13]=[CH:14][c:15]3[cH:16][c:17]([C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22][c:23]([C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28]3)[cH:29][c:30]([CH:31]=[O:32])[cH:33]2)[cH:34][c:35]([C:36]([CH3:37])([CH3:38])[CH3:39])[cH:40]1>>[CH3:1][C:2]...
CC(C)(C)c1cc(C=Cc2cc(C=O)cc(C=Cc3cc(C(C)(C)C)cc(C(C)(C)C)c3)c2)cc(C(C)(C)C)c1
CC(C)(C)c1cc(C=Cc2cc(C=Cc3cc(C(C)(C)C)cc(C(C)(C)C)c3)cc(CO)c2)cc(C(C)(C)C)c1
null
null
O1CCCC1
Reduction
Reduction of aldehydes and ketones to alcohols
e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7
21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a
C(=Cc1cccc(C=Cc2ccccc2)c1)c1ccccc1
[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]
87
[{"value": 87.0, "product": "C(C)(C)(C)C=1C=C(C=CC=2C=C(CO)C=C(C2)C=CC2=CC(=CC(=C2)C(C)(C)C)C(C)(C)C)C=C(C1)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.1, "product": "C(C)(C)(C)C=1C=C(C=CC=2C=C(CO)C=C(C2)C=CC2=CC(=CC(=C2)C(C)(C)C)C(C)(C)C)C=C(C1)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD...
null
null
null
null
A mixture of 3,5-bis(3′,5′-di-tert-butylstyryl)benzaldehyde (3.00 g, 6.61 mmol) and sodium borohydride (840 mg, 22.2 mmol) in tetrahydrofuran (150 cm3) was heated at reflux for 110 min. The solvent was then completely removed and light petroleum (30–40) and aqueous hydrochloric acid (3 M, 30 cm3) were added and stirred...
10.6084/m9.figshare.5104873.v1
null
Aldehyde
Primary alcohol
null
null
c1ccccc1.c1ccccc1.c1ccccc1
null
O1CCCC1
null
null
CC(C)(C)c1cc(C=Cc2cc(C=O)cc(C=Cc3cc(C(C)(C)C)cc(C(C)(C)C)c3)c2)cc(C(C)(C)C)c1>O1CCCC1>CC(C)(C)c1cc(C=Cc2cc(C=Cc3cc(C(C)(C)C)cc(C(C)(C)C)c3)cc(CO)c2)cc(C(C)(C)C)c1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-2bff57c9dfc8421dbe6ed3b86c52a9d7
C=COCCCl.Oc1ccc(C2CCCCC2)cc1>>C=COCCOc1ccc(C2CCCCC2)cc1
C1(CCCCC1)C1=CC=C(C=C1)O.C(=C)OCCCl.[OH-].[Na+].C(C)N(CC)CC>>C(=C)OCCOC1=CC=C(C=C1)C1CCCCC1
Cl[CH2:5][CH2:4][O:3][CH:2]=[CH2:1].[OH:6][c:7]1[cH:8][cH:9][c:10]([CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[cH:17][cH:18]1>>[CH2:1]=[CH:2][O:3][CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[cH:17][cH:18]1
C=COCCCl.Oc1ccc(C2CCCCC2)cc1
C=COCCOc1ccc(C2CCCCC2)cc1
null
[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC
C1(=CC=CC=C1)C
Heteroatom Alkylation and Arylation
Williamson Ether Synthesis
7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b
d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5
c1ccc(C2CCCCC2)cc1
Cl-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]=[C;D1;H2:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H2:5]=[C:4]-[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]
null
[]
null
null
null
null
In 300 ml of toluene, 83.1 g (0.5 mol) of p-cyclohexylphenol was dissolved and subsequently, 150 g of 2-chloroethyl vinyl ether, 25 g of sodium hydroxide, 5 g of tetrabutylammonium bromide and 60 g of triethylamine were added and reacted at 120° C. for 5 hours. The reaction solution was washed with water, excess chloro...
10.6084/m9.figshare.5104873.v1
null
Primary halide.Aromatic alcohol
Ether
null
null
c1ccccc1.C1CCCCC1
HCl
[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)C
null
null
C=COCCCl.Oc1ccc(C2CCCCC2)cc1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)C>C=COCCOc1ccc(C2CCCCC2)cc1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-9a3cf193af8f42ee80ecf03038968dc0
C=C(C)C(=O)O.C=C(C)C(=O)O.C=Cc1ccccc1>>C=C(C)C(=O)O.C=C(CC=Cc1ccccc1)C(=O)O
C1CO1.[Na].C(C(=C)C)(=O)O.S(=O)(=O)([O-])OOS(=O)(=O)[O-].[NH4+].[NH4+].C=CC1=CC=CC=C1.C(C(=C)C)(=O)O.C(C=C)(=O)OCCCC.S(=O)(=O)([O-])OOS(=O)(=O)[O-].[NH4+].[NH4+]>>C(=CC1=CC=CC=C1)CC(C(=O)O)=C.C(C=C)(=O)OCCCC.[Na].C1CO1.C(C(=C)C)(=O)O
[CH2:4]=[C:5]([CH3:6])[C:7](=[O:8])[OH:9].[CH2:10]=[C:11]([CH3:12])[C:21](=[O:22])[OH:23].[CH2:13]=[CH:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH2:4]=[C:5]([CH3:6])[C:7](=[O:8])[OH:9].[CH2:10]=[C:11]([CH2:12][CH:13]=[CH:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[C:21](=[O:22])[OH:23]
C=C(C)C(=O)O.C=C(C)C(=O)O.C=Cc1ccccc1
C=C(C)C(=O)O.C=C(CC=Cc1ccccc1)C(=O)O
null
null
O
C-C Coupling
OtherReaction
33e48384816274b5aff616852dc4f14f9c75728889ba8232dee5d0bd480280d7
48297e5b607b4624d5b08506879ba8f9dd47fb272c10888542fa01ef83829ef2
c1ccccc1
[C;D1;H2:1]=[C:2](-[CH3;D1;+0:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].[CH2;D1;+0:7]=[C:8]-[c:9]>>[C;D1;H2:1]=[C:2](-[CH2;D2;+0:3]-[CH;D2;+0:7]=[C:8]-[c:9])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6]
null
[]
75
CELSIUS
5
HOUR
In a reactor equipped with a stirring rod and a thermometer were placed 754 parts of water, 13 parts of a sodium salt of sulfuric acid ester of ethylene oxide adduct of methacrylic acid ELEMINOL RS-30 (trade name, available from Sanyo Chemical Industries, Ltd.,), 83 parts of styrene, 83 parts of methacrylic acid, 110 p...
10.6084/m9.figshare.5104873.v1
null
Vinyl
null
null
null
c1ccccc1
null
O
75
5
C=C(C)C(=O)O.C=C(C)C(=O)O.C=Cc1ccccc1>O>C=C(C)C(=O)O.C=C(CC=Cc1ccccc1)C(=O)O
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-424348839da04f94a84ae091f5ab15fa
BrCc1ccccc1.CCOC(=O)c1ccc(O)cc1>>CCOC(=O)c1ccc(OCc2ccccc2)cc1
C(=O)([O-])[O-].[Cs+].[Cs+].C(C1=CC=CC=C1)Br.C(=O)(C1=CC=CC=C1)CC1=CC=CC=C1.OC1=CC=C(C(=O)OCC)C=C1>>C(C1=CC=CC=C1)OC1=CC=C(C(=O)OCC)C=C1
Br[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([OH:10])[cH:18][cH:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19]1
BrCc1ccccc1.CCOC(=O)c1ccc(O)cc1
CCOC(=O)c1ccc(OCc2ccccc2)cc1
null
null
O.CN(C)C=O
Heteroatom Alkylation and Arylation
Williamson Ether Synthesis
7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b
d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5
c1ccc(COc2ccccc2)cc1
Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4]
100
[{"value": 100.0, "product": "C(C1=CC=CC=C1)OC1=CC=C(C(=O)OCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}]
null
null
null
null
35 mmol of benzyl bromide (BzBn, 35 mmol of ethyl 4-hydroxybenzoate (10), 14 g of Cs2CO3 and 40 ml of DMF were combined and stirred at RT ove night. Then the reaction mixture was poured into water and the product was collected by extraction. The organic solution was washed with brine and dried over MgSO4. After evapora...
10.6084/m9.figshare.5104873.v1
null
Primary halide.Aromatic alcohol
Ether
null
null
c1ccccc1.c1ccccc1
HBr
O.CN(C)C=O
null
null
BrCc1ccccc1.CCOC(=O)c1ccc(O)cc1>O.CN(C)C=O>CCOC(=O)c1ccc(OCc2ccccc2)cc1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-e893d8e4b615491698f2580374c37cef
CCOC(=O)c1ccc(OCc2ccccc2)cc1>>O=C(O)c1ccc(OCc2ccccc2)cc1
[OH-].[K+].C(C1=CC=CC=C1)OC1=CC=C(C(=O)OCC)C=C1>>C(C1=CC=CC=C1)OC1=CC=C(C(=O)O)C=C1
CC[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1
CCOC(=O)c1ccc(OCc2ccccc2)cc1
O=C(O)c1ccc(OCc2ccccc2)cc1
null
null
CO
Deprotection
Ester saponification (alkyl deprotection)
d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894
38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9
c1ccc(COc2ccccc2)cc1
C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]
null
[]
null
null
null
null
To the solution of 0.5 g KOH in 40 ml MeOH, was added 6.5 mmol of ethyl 4-benzyloxybenzoate. After the resulting mixture was refluxed for 4 hrs, the excess methanol was removed. The residue was mixed with 30 ml water and extracted with ether twice. The water solution was acidified with conc. HCl and extracted with ethy...
10.6084/m9.figshare.5104873.v1
null
Ester
Carboxylic acid
null
null
c1ccccc1.c1ccccc1
Other
CO
null
null
CCOC(=O)c1ccc(OCc2ccccc2)cc1>CO>O=C(O)c1ccc(OCc2ccccc2)cc1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-3687b0a5c976428fb52ff00b4203cdb7
CCCCCC[C@@H](OC(=O)c1ccc(OCc2ccccc2)cc1)C(F)(F)F>>CCCCCC[C@@H](OC(=O)c1ccc(O)cc1)C(F)(F)F
C(C1=CC=CC=C1)OC1=CC=C(C(=O)O[C@H](CCCCCC)C(F)(F)F)C=C1>>OC1=CC=C(C(=O)O[C@H](CCCCCC)C(F)(F)F)C=C1
c1ccc(C[O:15][c:14]2[cH:13][cH:12][c:11]([C:9]([O:8][C@H:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[C:18]([F:19])([F:20])[F:21])=[O:10])[cH:17][cH:16]2)cc1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]([O:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]1)[C:18]([F:19])([F:20])[F:21]
CCCCCC[C@@H](OC(=O)c1ccc(OCc2ccccc2)cc1)C(F)(F)F
CCCCCC[C@@H](OC(=O)c1ccc(O)cc1)C(F)(F)F
null
null
C(C)(=O)OCC
Deprotection
Hydroxyl benzyl deprotection
36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d
26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4
c1ccccc1
[c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4]
99
[{"value": 99.0, "product": "OC1=CC=C(C(=O)O[C@H](CCCCCC)C(F)(F)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}]
null
null
null
null
2.2 g of [R]-1-trifluoromethylheptyl 4-benzyloxybenzoate, (13) 100 mg of PdOH/C in 50 ml of ethyl acetate was stirred at RT over night under H2 atmosphere. Then the catalyst was filtered out and filtrate was evaporated to dryness to give the pure compound in yield of 99%. Conditions: See reaction.notes.procedure_detail...
10.6084/m9.figshare.5104873.v1
null
Ether
Aromatic alcohol
c1ccccc1
null
c1ccccc1
Other
C(C)(=O)OCC
null
null
CCCCCC[C@@H](OC(=O)c1ccc(OCc2ccccc2)cc1)C(F)(F)F>C(C)(=O)OCC>CCCCCC[C@@H](OC(=O)c1ccc(O)cc1)C(F)(F)F
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-9c10f800168b48649bfb59f8e3d09d94
C1=COCCC1.OCCCCBr>>BrCCCCOC1CCCCO1
BrCCCCO.O1CCCC=C1.C([O-])([O-])=O.[K+].[K+]>>BrCCCCOC1OCCCC1
[CH:7]1=[CH:8][CH2:9][CH2:10][CH2:11][O:12]1.[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6]>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:12]1
C1=COCCC1.OCCCCBr
BrCCCCOC1CCCCO1
null
null
P(=O)(Cl)(Cl)Cl.ClCCl
Heteroatom Alkylation and Arylation
oxa-Michael addition
abdcab389770d0a73be3b825aa1d56cee234da38dbdf3510fe8104d481e7cf3f
c6a3efa2acb508a32cdf9fcedfcd9635cce0ecdcf12c094b743aa576ea01fd9a
C1CCOCC1
[#8:1]1-[C:2]-[C:3]-[C:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-1.[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[CH;D3;+0:6]1-[#8:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-1
null
[]
null
null
24
HOUR
To a solution of commercially available 4-bromobutan-1-ol (16) (1 equi.) and 3,4-dihydropyran (17) (1.5 equi.) in dichloromethane (3 mL/mmole), phosphorus oxychloride (0.01 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h. Then potassium carbonate (1 equi.) was added t...
10.6084/m9.figshare.5104873.v1
null
Ether.Primary alcohol
Ether.Ether
C1=COCCC1
C1CCOCC1
C1CCOCC1
null
P(=O)(Cl)(Cl)Cl.ClCCl
null
24
C1=COCCC1.OCCCCBr>P(=O)(Cl)(Cl)Cl.ClCCl>BrCCCCOC1CCCCO1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-1f6cb91870914577b79f39714d7ce277
Fc1cccc(OCCCCOC2CCCCO2)c1F>>OCCCCOc1cccc(F)c1F
FC1=C(OCCCCOC2OCCCC2)C=CC=C1F.C1(=CC=C(C=C1)S(=O)(=O)O)C>>FC1=C(OCCCCO)C=CC=C1F
C1CCC([O:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][c:7]2[cH:8][cH:9][cH:10][c:11]([F:12])[c:13]2[F:14])OC1>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]([F:12])[c:13]1[F:14]
Fc1cccc(OCCCCOC2CCCCO2)c1F
OCCCCOc1cccc(F)c1F
null
null
O.CO.C1CCOC1
Reduction
Ether cleavage to primary alcohol
69ac283008defddd09d640f7879e86f66dd29371b5c835a2facf24163ef14e9f
a4561cbdd42f56679299e19ea8b11070a39a15f6a95fb8a877e677f11b7ff57f
c1ccccc1
[C:1]-[C:2]-[O;H0;D2;+0:3]-C1-C-C-C-C-O-1>>[C:1]-[C:2]-[OH;D1;+0:3]
null
[]
null
null
24
HOUR
To a solution of 2-[4-(2,3-difluorophenoxy)-butoxy]-tetrahydropyran (20) (1 equi.) and commercially available para-toluenesulfonic acid (21) (0.1 equi.) in methanol:THF (1:1) (3 mL/mmole), water (0.005 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h, quenched with wat...
10.6084/m9.figshare.5104873.v1
null
Ether.Ether
Primary alcohol
C1CCOCC1
null
c1ccccc1
HO-
O.CO.C1CCOC1
null
24
Fc1cccc(OCCCCOC2CCCCO2)c1F>O.CO.C1CCOC1>OCCCCOc1cccc(F)c1F
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-ed18f3b23e5b4b238c3b0edae8dd78e6
CCCCCBr.OCCCCOc1cccc(F)c1F>>CCCCCOCCCCOc1cccc(F)c1F
[H-].[Na+].FC1=C(OCCCCO)C=CC=C1F.BrCCCCC>>FC1=C(C(=CC=C1)OCCCCOCCCCC)F
Br[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16]([F:17])[c:18]1[F:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16]([F:17])[c:18]1[F:19]
CCCCCBr.OCCCCOc1cccc(F)c1F
CCCCCOCCCCOc1cccc(F)c1F
null
null
CN(C)C=O
Heteroatom Alkylation and Arylation
Williamson Ether Synthesis
dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c
46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca
c1ccccc1
Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[C:5]-[C:4]
null
[]
null
null
12
HOUR
Sodium hydride (1 equi.) was added to the solution of 4-(2,3-difluorophenoxy)-butan-1-ol (22), (1 equi.) and 1-bromopentane (1 equi.) in DMF (1 mL/mmole) and the reaction mixture was stirred at room temperature for 12 h,. quenched with water, extracted with ethyl acetate:hexane (1:1), washed with brine, dried over MgSO...
10.6084/m9.figshare.5104873.v1
null
Primary halide.Primary alcohol
Ether
null
null
c1ccccc1
HBr
CN(C)C=O
null
12
CCCCCBr.OCCCCOc1cccc(F)c1F>CN(C)C=O>CCCCCOCCCCOc1cccc(F)c1F
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-3e1233a3cb904efd828fd79e64ba9c58
CC(C)OB(OC(C)C)OC(C)C.CCCCCOCCCCOc1cccc(F)c1F>>CCCCCOCCCCOc1ccc(B(O)O)c(F)c1F
C(C)(C)OB(OC(C)C)OC(C)C.FC1=C(C(=CC=C1)OCCCCOCCCCC)F.C(CCC)[Li]>>FC1=C(C=CC(=C1F)OCCCCOCCCCC)B(O)O
CC(C)O[B:16]([O:17]C(C)C)[O:18]C(C)C.[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:19]([F:20])[c:21]1[F:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]([B:16]([OH:17])[OH:18])[c:19]([F:20])[c:21]1[F:2...
CC(C)OB(OC(C)C)OC(C)C.CCCCCOCCCCOc1cccc(F)c1F
CCCCCOCCCCOc1ccc(B(O)O)c(F)c1F
null
null
C1CCOC1
Functional Group Interconversion
OtherReaction
1f4aa60da129e13d59b25b8af621908349bb7a2fc229b3dd86a3dc8e049ee581
d6d312d46f766d2774f96de1fd96fd8f98a20e51a20ef3280f850cd6a3c77869
c1ccccc1
C-C(-C)-O-[B;H0;D3;+0:1](-[O;H0;D2;+0:2]-C(-C)-C)-[O;H0;D2;+0:3]-C(-C)-C.[F;D1;H0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[F;D1;H0:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[B;H0;D3;+0:1](-[OH;D1;+0:2])-[OH;D1;+0:3]):[c:8]:[c:9]
null
[]
null
null
2
HOUR
To a solution of 1,2-difluoro-3-(4-pentyloxybutoxy)-benzene (24), (1 equi.) in THF (5 mL/mmole), butyllithium (1.3 equi.) was added at −78° C. The reaction mixture was stirred at that temperature for 2 h,. Then triisopropylborate (1 equi.) was added at that temperature. The reaction mixture was stirred at that temperat...
10.6084/m9.figshare.5104873.v1
null
null
Boronic acid
c1ccccc1
c1ccccc1
c1ccccc1
HO-
C1CCOC1
null
2
CC(C)OB(OC(C)C)OC(C)C.CCCCCOCCCCOc1cccc(F)c1F>C1CCOC1>CCCCCOCCCCOc1ccc(B(O)O)c(F)c1F
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-0e36fea0a7614a60a1024966a981a2e5
CCCCCOCCCCOc1ccc(B(O)O)c(F)c1F.O=C(O)c1ccc(OCc2ccccc2)cc1>>CCCCCOCCCCOc1ccc(-c2ccc(C(=O)OCC)cc2)c(F)c1F
FC1=C(C=CC(=C1F)OCCCCOCCCCC)B(O)O.C(C1=CC=CC=C1)OC1=CC=C(C(=O)O)C=C1.C([O-])([O-])=O.[Na+].[Na+]>>C(C)OC(=O)C1=CC=C(C=C1)C1=C(C(=C(C=C1)OCCCCOCCCCC)F)F
OB(O)[c:15]1[cH:14][cH:13][c:12]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:29]([F:30])[c:27]1[F:28].c1cc[c:24](CO[c:16]2[cH:17][cH:18][c:19]([C:20](=[O:21])[OH:22])[cH:25][cH:26]2)[cH:23]c1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH...
CCCCCOCCCCOc1ccc(B(O)O)c(F)c1F.O=C(O)c1ccc(OCc2ccccc2)cc1
CCCCCOCCCCOc1ccc(-c2ccc(C(=O)OCC)cc2)c(F)c1F
null
C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1
O.C1(=CC=CC=C1)C
Heteroatom Alkylation and Arylation
OtherReaction
ef28868b225a2450c6548e9941616465dfd26b50cf02b7e17a84a41c450cb001
7e05a2b134185de5b7c3bf24aa876891a2e91e7b2feb4a33d7d8bfc3de600c53
c1ccc(-c2ccccc2)cc1
O-B(-O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[O;D1;H0:7]=[C:8](-[OH;D1;+0:9])-[c:10]1:[c:11]:[c:12]:[c;H0;D3;+0:13](-O-C-[c;H0;D3;+0:14]2:[cH;D2;+0:15]:c:c:c:c:2):[c:16]:[c:17]:1>>[CH3;D1;+0:14]-[CH2;D2;+0:15]-[O;H0;D2;+0:9]-[C:8](=[O;D1;H0:7])-[c:10]1:[c:11]:[c:12]:[c;H0;D3;+0:13](-[c;H0;D3;+0:1](:[c...
88
[{"value": 88.0, "product": "C(C)OC(=O)C1=CC=C(C=C1)C1=C(C(=C(C=C1)OCCCCOCCCCC)F)F", "details": "PERCENTYIELD", "is_desired": false}]
null
null
12
HOUR
A biphasic solution of 2,3-difluoro-4-(4-pentyloxybutoxy)phenylboronic acid (25): (1 equi.), 4-bromo-benzoic acid ethyl ester (12), (1 equi.), sodium carbonate (2.7 equi.), and Pd(PPh3)4 catalyst (0.01 equi.) in water-toluene (1:1) (2 mL/mmole) was stirred at 100 C. temperature for 12 h., cooled to room temperature, ex...
10.6084/m9.figshare.5104873.v1
null
Carboxylic acid.Ether.Boronic acid
Ester
c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1
HO-.B
C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C1(=CC=CC=C1)C
null
12
CCCCCOCCCCOc1ccc(B(O)O)c(F)c1F.O=C(O)c1ccc(OCc2ccccc2)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C1(=CC=CC=C1)C>CCCCCOCCCCOc1ccc(-c2ccc(C(=O)OCC)cc2)c(F)c1F
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-a26dd92f0c2a4f80bcbf1d5d19358e72
CCCCCC[C@@H](OC(=O)c1ccc(O)cc1)C(F)(F)F.CCCCOCCCCOc1ccc(-c2ccc(C(=O)O)cc2)c(F)c1F>>CCCCCC[C@@H](OC(=O)c1ccc(OC(=O)c2ccc(-c3ccc(OCCCCOCCCCC)c(F)c3F)cc2)cc1)C(F)(F)F
C(CCC)OCCCCOC1=C(C(=C(C=C1)C1=CC=C(C=C1)C(=O)O)F)F.FC([C@@H](CCCCCC)OC(C1=CC=C(C=C1)O)=O)(F)F.CN(C)C1=NC=CC=C1>>FC([C@@H](CCCCCC)OC(=O)C1=CC=C(C=C1)OC(=O)C1=CC=C(C=C1)C1=C(C(=C(C=C1)OCCCCOCCCCC)F)F)(F)F
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]([O:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([OH:15])[cH:43][cH:44]1)[C:45]([F:46])([F:47])[F:48].O[C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21](-[c:22]2[cH:23][cH:24][c:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH2:34][CH3:35])[c:37]([F:38])[c:39...
CCCCCC[C@@H](OC(=O)c1ccc(O)cc1)C(F)(F)F.CCCCOCCCCOc1ccc(-c2ccc(C(=O)O)cc2)c(F)c1F
CCCCCC[C@@H](OC(=O)c1ccc(OC(=O)c2ccc(-c3ccc(OCCCCOCCCCC)c(F)c3F)cc2)cc1)C(F)(F)F
null
null
C1CCOC1.C(C)(C)N=C=NC(C)C
Acylation
OtherReaction
f18451ac648b00cb7c6684a3e64bee855b0320c7eb0f62b757b29d5fb6745560
1489fe0065c6531b60fda87a3857d7da1cd21873868856f058c20706f927fa08
O=C(Oc1ccccc1)c1ccc(-c2ccccc2)cc1
O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[CH3;D1;+0:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C:6]-[C:7]-[CH2;D2;+0:8]-[C;D1;H3:13].[O;D1;H0:2]=[C;H0;D3;+0:1](-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12])-[c:3](:[c:4]):[c:5]
65
[{"value": 65.0, "product": "FC([C@@H](CCCCCC)OC(=O)C1=CC=C(C=C1)OC(=O)C1=CC=C(C=C1)C1=C(C(=C(C=C1)OCCCCOCCCCC)F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}]
null
null
24
HOUR
To a solution of 4′-(4-butoxybutoxy)-2′,3′-difluorobiphenyl-4-carboxylic acid (27) (1 equi.), (4-hydroxybenzoic acid (R)-1-trifluoromethyl-heptyl ester (7) (1 equi.), and DMAP (dimethylaminopyridine) (0.1 equi.) in THF (25 mL/mmole), DIC (diisopropyl carbodiimide) (1.2 equi.) was added at room temperature. The reaction...
10.6084/m9.figshare.5104873.v1
null
Carboxylic acid.Aromatic alcohol
Ester
null
null
c1ccccc1.c1ccccc1.c1ccccc1
null
C1CCOC1.C(C)(C)N=C=NC(C)C
null
24
CCCCCC[C@@H](OC(=O)c1ccc(O)cc1)C(F)(F)F.CCCCOCCCCOc1ccc(-c2ccc(C(=O)O)cc2)c(F)c1F>C1CCOC1.C(C)(C)N=C=NC(C)C>CCCCCC[C@@H](OC(=O)c1ccc(OC(=O)c2ccc(-c3ccc(OCCCCOCCCCC)c(F)c3F)cc2)cc1)C(F)(F)F
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-897b02d40a5c415e94fa7c6fe1ac97fb
C1=COCCC1.OCCCCBr>>BrCCCCOC1CCCCO1
BrCCCCO.O1CCCC=C1.C([O-])([O-])=O.[K+].[K+]>>BrCCCCOC1OCCCC1
[CH:7]1=[CH:8][CH2:9][CH2:10][CH2:11][O:12]1.[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6]>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:12]1
C1=COCCC1.OCCCCBr
BrCCCCOC1CCCCO1
null
null
P(=O)(Cl)(Cl)Cl.ClCCl
Heteroatom Alkylation and Arylation
oxa-Michael addition
abdcab389770d0a73be3b825aa1d56cee234da38dbdf3510fe8104d481e7cf3f
c6a3efa2acb508a32cdf9fcedfcd9635cce0ecdcf12c094b743aa576ea01fd9a
C1CCOCC1
[#8:1]1-[C:2]-[C:3]-[C:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-1.[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[CH;D3;+0:6]1-[#8:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-1
null
[]
null
null
24
HOUR
To a solution of commercially available 4-bromobutan-1-ol (16) (1 equi.) and 3,4-dihydropyran (17) (1.5 equi.) in dichloromethane (3 mL/mmole), phosphorus oxychloride (0.01 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h. Then potassium carbonate (1 equi.) was added t...
10.6084/m9.figshare.5104873.v1
null
Ether.Primary alcohol
Ether.Ether
C1=COCCC1
C1CCOCC1
C1CCOCC1
null
P(=O)(Cl)(Cl)Cl.ClCCl
null
24
C1=COCCC1.OCCCCBr>P(=O)(Cl)(Cl)Cl.ClCCl>BrCCCCOC1CCCCO1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-96173bef1136419e80caf61235bb990a
Fc1cccc(OCCCCOC2CCCCO2)c1F>>OCCCCOc1cccc(F)c1F
FC1=C(OCCCCOC2OCCCC2)C=CC=C1F.C1(=CC=C(C=C1)S(=O)(=O)O)C>>FC1=C(OCCCCO)C=CC=C1F
C1CCC([O:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][c:7]2[cH:8][cH:9][cH:10][c:11]([F:12])[c:13]2[F:14])OC1>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]([F:12])[c:13]1[F:14]
Fc1cccc(OCCCCOC2CCCCO2)c1F
OCCCCOc1cccc(F)c1F
null
null
O.CO.C1CCOC1
Reduction
Ether cleavage to primary alcohol
69ac283008defddd09d640f7879e86f66dd29371b5c835a2facf24163ef14e9f
a4561cbdd42f56679299e19ea8b11070a39a15f6a95fb8a877e677f11b7ff57f
c1ccccc1
[C:1]-[C:2]-[O;H0;D2;+0:3]-C1-C-C-C-C-O-1>>[C:1]-[C:2]-[OH;D1;+0:3]
null
[]
null
null
24
HOUR
To a solution of 2-[4-(2,3-difluorophenoxy)-butoxy]-tetrahydropyran (20) (1 equi.) and commercially available para-toluenesulfonic acid (21) (0.1 equi.) in methanol:THF (1:1) (3 mL/mmole), water (0.005 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h, quenched with wat...
10.6084/m9.figshare.5104873.v1
null
Ether.Ether
Primary alcohol
C1CCOCC1
null
c1ccccc1
HO-
O.CO.C1CCOC1
null
24
Fc1cccc(OCCCCOC2CCCCO2)c1F>O.CO.C1CCOC1>OCCCCOc1cccc(F)c1F
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-ca4916b0463d4f1792f864461fb1227c
CCCCCBr.OCCCCOc1cccc(F)c1F>>CCCCCOCCCCOc1cccc(F)c1F
[H-].[Na+].FC1=C(OCCCCO)C=CC=C1F.BrCCCCC>>FC1=C(C(=CC=C1)OCCCCOCCCCC)F
Br[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16]([F:17])[c:18]1[F:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16]([F:17])[c:18]1[F:19]
CCCCCBr.OCCCCOc1cccc(F)c1F
CCCCCOCCCCOc1cccc(F)c1F
null
null
CN(C)C=O
Heteroatom Alkylation and Arylation
Williamson Ether Synthesis
dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c
46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca
c1ccccc1
Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[C:5]-[C:4]
null
[]
null
null
12
HOUR
Sodium hydride (1 equi.) was added to the solution of 4-(2,3-difluorophenoxy)-butan-1-ol (22), (1 equi.) and 1-bromopentane (1 equi.) in DMF (1 mL/mmole) and the reaction mixture was stirred at room temperature for 12 h,. quenched with water, extracted with ethyl acetate:hexane (1:1), washed with brine, dried over MgSO...
10.6084/m9.figshare.5104873.v1
null
Primary halide.Primary alcohol
Ether
null
null
c1ccccc1
HBr
CN(C)C=O
null
12
CCCCCBr.OCCCCOc1cccc(F)c1F>CN(C)C=O>CCCCCOCCCCOc1cccc(F)c1F
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-88ca5467e26b4c35bf2cc8686a6850bf
CC(C)OB(OC(C)C)OC(C)C.CCCCCOCCCCOc1cccc(F)c1F>>CCCCCOCCCCOc1ccc(B(O)O)c(F)c1F
C(C)(C)OB(OC(C)C)OC(C)C.FC1=C(C(=CC=C1)OCCCCOCCCCC)F.C(CCC)[Li]>>FC1=C(C=CC(=C1F)OCCCCOCCCCC)B(O)O
CC(C)O[B:16]([O:17]C(C)C)[O:18]C(C)C.[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:19]([F:20])[c:21]1[F:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]([B:16]([OH:17])[OH:18])[c:19]([F:20])[c:21]1[F:2...
CC(C)OB(OC(C)C)OC(C)C.CCCCCOCCCCOc1cccc(F)c1F
CCCCCOCCCCOc1ccc(B(O)O)c(F)c1F
null
null
C1CCOC1
Functional Group Interconversion
OtherReaction
1f4aa60da129e13d59b25b8af621908349bb7a2fc229b3dd86a3dc8e049ee581
d6d312d46f766d2774f96de1fd96fd8f98a20e51a20ef3280f850cd6a3c77869
c1ccccc1
C-C(-C)-O-[B;H0;D3;+0:1](-[O;H0;D2;+0:2]-C(-C)-C)-[O;H0;D2;+0:3]-C(-C)-C.[F;D1;H0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[F;D1;H0:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[B;H0;D3;+0:1](-[OH;D1;+0:2])-[OH;D1;+0:3]):[c:8]:[c:9]
null
[]
null
null
2
HOUR
To a solution of 1,2-difluoro-3-(4-pentyloxybutoxy)-benzene (24), (1 equi.) in THF (5 mL/mmole), butyllithium (1.3 equi.) was added at −78° C. The reaction mixture was stirred at that temperature for 2 hr,. Then triisopropylborate (1 equi.) was added at that temperature. The reaction mixture was stirred at that tempera...
10.6084/m9.figshare.5104873.v1
null
null
Boronic acid
c1ccccc1
c1ccccc1
c1ccccc1
HO-
C1CCOC1
null
2
CC(C)OB(OC(C)C)OC(C)C.CCCCCOCCCCOc1cccc(F)c1F>C1CCOC1>CCCCCOCCCCOc1ccc(B(O)O)c(F)c1F
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-6ad8b409962b46c38cd36eb904e5406a
CCCCCOCCCCOc1ccc(B(O)O)c(F)c1F.O=C(O)c1ccc(OCc2ccccc2)cc1>>CCCCCOCCCCOc1ccc(-c2ccc(C(=O)OCC)cc2)c(F)c1F
FC1=C(C=CC(=C1F)OCCCCOCCCCC)B(O)O.C(C1=CC=CC=C1)OC1=CC=C(C(=O)O)C=C1.C([O-])([O-])=O.[Na+].[Na+]>>C(C)OC(=O)C1=CC=C(C=C1)C1=C(C(=C(C=C1)OCCCCOCCCCC)F)F
OB(O)[c:15]1[cH:14][cH:13][c:12]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:29]([F:30])[c:27]1[F:28].c1cc[c:24](CO[c:16]2[cH:17][cH:18][c:19]([C:20](=[O:21])[OH:22])[cH:25][cH:26]2)[cH:23]c1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH...
CCCCCOCCCCOc1ccc(B(O)O)c(F)c1F.O=C(O)c1ccc(OCc2ccccc2)cc1
CCCCCOCCCCOc1ccc(-c2ccc(C(=O)OCC)cc2)c(F)c1F
null
C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1
O.C1(=CC=CC=C1)C
Heteroatom Alkylation and Arylation
OtherReaction
ef28868b225a2450c6548e9941616465dfd26b50cf02b7e17a84a41c450cb001
7e05a2b134185de5b7c3bf24aa876891a2e91e7b2feb4a33d7d8bfc3de600c53
c1ccc(-c2ccccc2)cc1
O-B(-O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[O;D1;H0:7]=[C:8](-[OH;D1;+0:9])-[c:10]1:[c:11]:[c:12]:[c;H0;D3;+0:13](-O-C-[c;H0;D3;+0:14]2:[cH;D2;+0:15]:c:c:c:c:2):[c:16]:[c:17]:1>>[CH3;D1;+0:14]-[CH2;D2;+0:15]-[O;H0;D2;+0:9]-[C:8](=[O;D1;H0:7])-[c:10]1:[c:11]:[c:12]:[c;H0;D3;+0:13](-[c;H0;D3;+0:1](:[c...
88
[{"value": 88.0, "product": "C(C)OC(=O)C1=CC=C(C=C1)C1=C(C(=C(C=C1)OCCCCOCCCCC)F)F", "details": "PERCENTYIELD", "is_desired": false}]
null
null
12
HOUR
A biphasic solution of 2,3-difluoro-4-(4-pentyloxybutoxy)phenylboronic acid (25) (1 equi.), 4-bromo-benzoic acid ethyl ester (12), (1 equi.), sodium carbonate (2.7 equi.), and tetrakis(triphenylphoshine)palladium catalyst (0.01 equi.) in water-toluene (1:1) (2 mL/mmole) was stirred at 100 C. temperature for 12 h., cool...
10.6084/m9.figshare.5104873.v1
null
Carboxylic acid.Ether.Boronic acid
Ester
c1ccccc1.c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1
c1ccccc1.c1ccccc1
HO-.B
C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C1(=CC=CC=C1)C
null
12
CCCCCOCCCCOc1ccc(B(O)O)c(F)c1F.O=C(O)c1ccc(OCc2ccccc2)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C1(=CC=CC=C1)C>CCCCCOCCCCOc1ccc(-c2ccc(C(=O)OCC)cc2)c(F)c1F
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-66e871d4bd824865a6d3a12ea3da7ade
CCCCCC[C@@H](OC(=O)c1ccc(OCc2ccccc2)cc1)C(F)(F)F.CCCCOCCCCOc1ccc(-c2ccc(C(=O)O)cc2)c(F)c1F.CN(C)c1ccccn1>>CCCCCC[C@@H](OC(=O)c1ccc(OC(=O)c2ccc(-c3ccc(OCCCCOCCCCC)c(F)c3F)cc2)cc1)C(F)(F)F
C(CCC)OCCCCOC1=C(C(=C(C=C1)C1=CC=C(C=C1)C(=O)O)F)F.C(C1=CC=CC=C1)OC1=CC=C(C(=O)O[C@H](CCCCCC)C(F)(F)F)C=C1.CN(C)C1=NC=CC=C1>>FC([C@@H](CCCCCC)OC(=O)C1=CC=C(C=C1)OC(=O)C1=CC=C(C=C1)C1=C(C(=C(C=C1)OCCCCOCCCCC)F)F)(F)F
c1ccc(C[O:15][c:14]2[cH:13][cH:12][c:11]([C:9]([O:8][C@H:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[C:45]([F:46])([F:47])[F:48])=[O:10])[cH:44][cH:43]2)cc1.O[C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21](-[c:22]2[cH:23][cH:24][c:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH2:34][CH3:35])[c:37]([F:...
CCCCCC[C@@H](OC(=O)c1ccc(OCc2ccccc2)cc1)C(F)(F)F.CCCCOCCCCOc1ccc(-c2ccc(C(=O)O)cc2)c(F)c1F.CN(C)c1ccccn1
CCCCCC[C@@H](OC(=O)c1ccc(OC(=O)c2ccc(-c3ccc(OCCCCOCCCCC)c(F)c3F)cc2)cc1)C(F)(F)F
null
null
C1CCOC1.C(C)(C)N=C=NC(C)C
Acylation
OtherReaction
b4a57e94cb7a12881c67e0e26b8193d647c5cc43d8edaed86855146cbda64891
f3ca5eb187fce22450e82b66f92c0fb9a302be49e03dbd0ea0aff8662c91d723
O=C(Oc1ccccc1)c1ccc(-c2ccccc2)cc1
C-N(-[CH3;D1;+0:1])-c1:c:c:c:c:n:1.O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[CH3;D1;+0:9].[c:10]:[c:11](-[O;H0;D2;+0:12]-C-c1:c:c:c:c:c:1):[c:13]>>[C:7]-[C:8]-[CH2;D2;+0:9]-[CH3;D1;+0:1].[O;D1;H0:3]=[C;H0;D3;+0:2](-[O;H0;D2;+0:12]-[c:11](:[c:10]):[c:13])-[c:4](:[c:5]):[c:6]
65
[{"value": 65.0, "product": "FC([C@@H](CCCCCC)OC(=O)C1=CC=C(C=C1)OC(=O)C1=CC=C(C=C1)C1=C(C(=C(C=C1)OCCCCOCCCCC)F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}]
null
null
24
HOUR
To a solution of 4′-(4-butoxybutoxy)-2′,3′-difluorobiphenyl-4-carboxylic acid (27) (1 equi.), (4-hydroxybenzoic acid (R)-1-trifluoromethyl-heptyl ester (13, Scheme 7) (1 equi.), and DMAP (dimethylaminopyridine) (0.1 equi.) in THF (25 mL/mmole), DIC (diisopropyl carbodiimide) (1.2 equi.) was added at room temperature. T...
10.6084/m9.figshare.5104873.v1
null
Carboxylic acid.Ether.Tertiary amine
Ester
c1ccccc1.c1ccncc1
null
c1ccccc1.c1ccccc1.c1ccccc1
HO-
C1CCOC1.C(C)(C)N=C=NC(C)C
null
24
CCCCCC[C@@H](OC(=O)c1ccc(OCc2ccccc2)cc1)C(F)(F)F.CCCCOCCCCOc1ccc(-c2ccc(C(=O)O)cc2)c(F)c1F.CN(C)c1ccccn1>C1CCOC1.C(C)(C)N=C=NC(C)C>CCCCCC[C@@H](OC(=O)c1ccc(OC(=O)c2ccc(-c3ccc(OCCCCOCCCCC)c(F)c3F)cc2)cc1)C(F)(F)F
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-9738564159bc4fc6bc633e268b9088a2
COc1ccc(CC(C)=O)cc1OC>>COc1ccc(C[C@H](C)O)cc1OC
COC=1C=C(C=CC1OC)CC(C)=O.C=1N=C(C2=C(N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(O)OC[C@@H]4[C@H]([C@H]([C@@H](O4)N5C=CCC(=C5)C(=O)N)O)O)O)OP(=O)(O)O)N.C=1N=C(C2=C(N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(O)OC[C@@H]4[C@H]([C@H]([C@@H](O4)N5C=CCC(=C5)C(=O)N)O)O)O)OP(=O)(O)O)N>>COC=1C=C(C=CC1OC...
[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C:8]([CH3:9])=[O:10])[cH:11][c:12]1[O:13][CH3:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C@H:8]([CH3:9])[OH:10])[cH:11][c:12]1[O:13][CH3:14]
COc1ccc(CC(C)=O)cc1OC
COc1ccc(C[C@H](C)O)cc1OC
null
null
null
Reduction
Reduction of ketone to secondary alcohol
02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070
1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89
c1ccccc1
[C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[C:4]-[c:5]>>[C;D1;H3:1]-[C@H;D3;+0:2](-[OH;D1;+0:3])-[C:4]-[c:5]
null
[]
null
null
null
null
The carbonyl reductases of the present invention can utilize NADPH as a coenzyme, have no alcohol dehydrogenating activity, and reduce 3,4-dimethoxyphenylacetone by utilizing NADPH as a coenzyme to produce 90% ee or more (S)-1-(3,4-dimethoxyphenyl)-2-propanol. Conditions: See reaction.notes.procedure_details.
10.6084/m9.figshare.5104873.v1
null
Ketone
Secondary alcohol
null
null
c1ccccc1
null
null
null
null
COc1ccc(CC(C)=O)cc1OC>>COc1ccc(C[C@H](C)O)cc1OC
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-cf2f96f6b259443b9d352b9132f225ad
COCCC(C)(OC)OC.Nc1cccc(Cl)c1>>Cc1ccnc2cc(Cl)ccc12
ClC=1C=C(N)C=CC1.COCCC(C)(OC)OC>>ClC1=CC=C2C(=CC=NC2=C1)C
CO[C:2](OC)([CH3:1])[CH2:3][CH2:4]OC.[NH2:5][c:6]1[cH:7][c:8]([Cl:9])[cH:10][cH:11][cH:12]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]2[cH:7][c:8]([Cl:9])[cH:10][cH:11][c:12]12
COCCC(C)(OC)OC.Nc1cccc(Cl)c1
Cc1ccnc2cc(Cl)ccc12
null
[Cl-].[Zn+2].[Cl-]
C(C)O
Aromatic Heterocycle Formation
OtherReaction
637b257c32cb63a8e650eed0785ae845bd11755c2192778f34708cecd0ddd24c
37da407ba22aeb87f9320448e7710117027e549cd7c89e722598c54789c5481f
c1ccc2ncccc2c1
C-O-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[C;H0;D4;+0:3](-[C;D1;H3:4])(-O-C)-O-C.[NH2;D1;+0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[C;D1;H3:4]-[c;H0;D3;+0:3]1:[cH;D2;+0:2]:[cH;D2;+0:1]:[n;H0;D2;+0:5]:[c:6](:[c:7]):[c;H0;D3;+0:8]:1:[c:9]:[c:10]
null
[]
null
null
8
HOUR
To a mixture containing 3-chloroaniline (1.59 g), ferric chloride hexahydrate (5.4 g), zinc chloride (0.2 g), ethanol (20 ml of 95% aqueous solution) preheated to 60° C. was added 1,3,3-trimethoxybutane (1.48 g). The resulting mixture was refluxed for two hours and allowed to stand overnight. The volatile matrials were...
10.6084/m9.figshare.5104873.v1
null
Ether.Ether.Ether.Primary amine
null
c1ccccc1
c1ccc2ncccc2c1
c1ccc2ncccc2c1
HO-
[Cl-].[Zn+2].[Cl-].C(C)O
null
8
COCCC(C)(OC)OC.Nc1cccc(Cl)c1>[Cl-].[Zn+2].[Cl-].C(C)O>Cc1ccnc2cc(Cl)ccc12
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-6a873647e2b44ce99055068705e47796
CI.Cc1ccnc2cc(Cl)ccc12>>Cc1cc[n+](C)c2cc(Cl)ccc12.[I-]
ClC1=CC=C2C(=CC=NC2=C1)C.CI.C(C)OCC>>[I-].ClC1=CC=C2C(=CC=[N+](C2=C1)C)C
[CH3:6][I:14].[CH3:1][c:2]1[cH:3][cH:4][n:5][c:7]2[cH:8][c:9]([Cl:10])[cH:11][cH:12][c:13]12>>[CH3:1][c:2]1[cH:3][cH:4][n+:5]([CH3:6])[c:7]2[cH:8][c:9]([Cl:10])[cH:11][cH:12][c:13]12.[I-:14]
CI.Cc1ccnc2cc(Cl)ccc12
Cc1cc[n+](C)c2cc(Cl)ccc12.[I-]
null
null
CC#N
Functional Group Interconversion
OtherReaction
937ea022dcada6555346bd5cf066a360c7571b4bc94939875aa1ba8e96ea1397
f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71
c1ccc2[nH+]cccc2c1
[CH3;D1;+0:1]-[I;H0;D1;+0:2].[c:3]:[c:4](:[c:5]):[n;H0;D2;+0:6]:[c:7]:[c:8]>>[CH3;D1;+0:1]-[n+;H0;D3:6](:[c:7]:[c:8]):[c:4](:[c:3]):[c:5].[I-;H0;D0:2]
null
[]
null
null
null
null
A portion of the 7-chlorolepidine (80 mg) prepared as above was methylated by heating with CH3I (0.5 ml) in CH3CN (1 ml) at reflux for two hours. The mixture was treated with diethyl ether, followed by centrifugation, to give a yellow powder. Conditions: See reaction.notes.procedure_details. Workup: at reflux for two h...
10.6084/m9.figshare.5104873.v1
null
null
null
c1ccc2ncccc2c1
C1=Cc2ccccc2[NH+]=C1
C1=Cc2ccccc2[NH+]=C1
null
CC#N
null
null
CI.Cc1ccnc2cc(Cl)ccc12>CC#N>Cc1cc[n+](C)c2cc(Cl)ccc12.[I-]
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-4307fdaae0dc4d9bb621a9607ef82b36
Brc1cccc(C2OCCO2)c1.O=C1Nc2ccccc2C1=O>>O=C1C(=O)N(c2cccc(C3OC=CO3)c2)c2ccccc21
BrC=1C=C(C=CC1)C1OCCO1.CO.[H-].[Na+].N1C(=O)C(=O)C2=CC=CC=C12>>O1C(OC=C1)C=1C=C(C=CC1)N1C(=O)C(=O)C2=CC=CC=C12
Br[c:6]1[cH:7][cH:8][cH:9][c:10]([CH:11]2[O:12][CH2:13][CH2:14][O:15]2)[cH:16]1.[O:1]=[C:2]1[C:3](=[O:4])[NH:5][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21>>[O:1]=[C:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][cH:8][cH:9][c:10]([CH:11]3[O:12][CH:13]=[CH:14][O:15]3)[cH:16]2)[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21
Brc1cccc(C2OCCO2)c1.O=C1Nc2ccccc2C1=O
O=C1C(=O)N(c2cccc(C3OC=CO3)c2)c2ccccc21
null
[Cu]I
C(Cl)(Cl)Cl.CN(C)C=O
Heteroatom Alkylation and Arylation
OtherReaction
93f5a2c2e5e4c9b14b9bc8f83a730160c3fc67c49d749f704142771907329373
1d937d7149881ab21c35c386ba54ae401a9ffca81b338b7fa4a76e646bc2031b
O=C1C(=O)N(c2cccc(C3OC=CO3)c2)c2ccccc21
Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]1-[#8:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[#8:8]-1):[c:9]:[c:10].[O;D1;H0:11]=[C:12]1-[c:13]:[c:14](:[c:15])-[NH;D2;+0:16]-[C:17]-1=[O;D1;H0:18]>>[O;D1;H0:11]=[C:12]1-[c:13]:[c:14](:[c:15])-[N;H0;D3;+0:16](-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]2-[#8:5]-[CH;D2;+0:6]=[CH;D2;+0:7]-[#8:8]-2):[c:9...
null
[]
0
CELSIUS
1.5
HOUR
Isatin (3.2 g, 0.0218 mol) was dissolved in anhydrous DMF (75 mL) and cooled in an ice-bath under a nitrogen atmosphere. To this cold solution, sodium hydride (0.575 g, 0.0239 mol) was added and the reaction was stirred at 0° C. for 1.5 hours. This solution was then treated with 2-(3-bromophenyl)-1,3-dioxolane (5 g, 1 ...
10.6084/m9.figshare.5104873.v1
null
Aromatic halide.Ether.Ether.Secondary amide
Ether.Ether.Tertiary amide
c1ccccc1.C1COCO1.c1ccc2c(c1)CCN2
c1ccccc1.C1=COCO1.c1ccc2c(c1)CC[NH]2
c1ccccc1.C1=COCO1.c1ccc2c(c1)CC[NH]2
HBr
[Cu]I.C(Cl)(Cl)Cl.CN(C)C=O
0
1.5
Brc1cccc(C2OCCO2)c1.O=C1Nc2ccccc2C1=O>[Cu]I.C(Cl)(Cl)Cl.CN(C)C=O>O=C1C(=O)N(c2cccc(C3OC=CO3)c2)c2ccccc21
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-10387fc676524c57a88f49116ff26a5c
ClCc1ccc(OCc2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>[Cl-].c1ccc(COc2ccc(C[P+](c3ccccc3)(c3ccccc3)c3ccccc3)cc2)cc1
C(C1=CC=CC=C1)OC1=CC=C(CCl)C=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CCOCC>>[Cl-].C(C1=CC=CC=C1)OC1=CC=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1
[Cl:1][CH2:12][c:11]1[cH:10][cH:9][c:8]([O:7][CH2:6][c:5]2[cH:4][cH:3][cH:2][cH:35][cH:34]2)[cH:33][cH:32]1.[P:13]([c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)([c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[Cl-:1].[cH:2]1[cH:3][cH:4][c:5]([CH2:6][O:7][c:8]2[cH:9][cH:10][c:11](...
ClCc1ccc(OCc2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1
[Cl-].c1ccc(COc2ccc(C[P+](c3ccccc3)(c3ccccc3)c3ccccc3)cc2)cc1
null
null
C1(=CC=CC=C1)C
Functional Group Interconversion
OtherReaction
72a5231b07f184f0ef4a0648badd4176f521b95f1ba3340a0f90d8894af47260
47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508
c1ccc(COc2ccc(C[P+](c3ccccc3)(c3ccccc3)c3ccccc3)cc2)cc1
[Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5].[c:6]:[c:7](-[P;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15]>>[Cl-;H0;D0:1].[c:4]:[c:3](-[CH2;D2;+0:2]-[P+;H0;D4:8](-[c:7](:[c:6]):[c:15])(-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:5]
null
[]
null
null
null
null
4-Benzyloxybenzyl chloride (1 g, 0.0043 mol) and triphenyl phosphine (1.127 g, 1 equivalent) in anhydrous toluene (20 mL) were refluxed under nitrogen for ˜8–10 hours. A white precipitate appeared in the reaction mixture. The reaction mixture was then cooled to room temperature and ether (100 mL) was added. The precipi...
10.6084/m9.figshare.5104873.v1
null
Primary halide
null
null
null
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
null
C1(=CC=CC=C1)C
null
null
ClCc1ccc(OCc2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C1(=CC=CC=C1)C>[Cl-].c1ccc(COc2ccc(C[P+](c3ccccc3)(c3ccccc3)c3ccccc3)cc2)cc1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-22369baf791041d692ac21ca9695965b
COc1ccc(CCl)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>COc1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.[Cl-]
COC1=CC=C(CCl)C=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>[Cl-].COC1=CC=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1
[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][Cl:29])[cH:27][cH:28]1.[P:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][P+:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)([c:15]2[cH:16][cH:17...
COc1ccc(CCl)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1
COc1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.[Cl-]
null
null
CCOCC.C1(=CC=CC=C1)C
Functional Group Interconversion
OtherReaction
72a5231b07f184f0ef4a0648badd4176f521b95f1ba3340a0f90d8894af47260
47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508
c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
[Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5].[c:6]:[c:7](-[P;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15]>>[Cl-;H0;D0:1].[c:6]:[c:7](-[P+;H0;D4:8](-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5])(-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15]
null
[]
null
null
null
null
A solution of 4-methoxybenzyl chloride (1.153 g, 0.0074 mol) in anhydrous toluene (10 mL) was treated with triphenylphosphine (1.93 g, 1 equivalent). The resulting solution was refluxed under nitrogen. After 8–10 hours, the reaction was cooled to room temperature and diluted with ether. The phosphonium salt was collect...
10.6084/m9.figshare.5104873.v1
null
Primary halide
null
null
null
c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1
null
CCOCC.C1(=CC=CC=C1)C
null
null
COc1ccc(CCl)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>CCOCC.C1(=CC=CC=C1)C>COc1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.[Cl-]
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-c0b1f5fc553446359bccb5846409ec6d
O=Cc1ccc(Br)cc1.OCCO>>Brc1ccc(C2OCCO2)cc1
O.BrC1=CC=C(C=O)C=C1.O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(CO)O>>BrC1=CC=C(C=C1)C1OCCO1
[Br:1][c:2]1[cH:3][cH:4][c:5]([CH:6]=[O:7])[cH:11][cH:12]1.O[CH2:8][CH2:9][OH:10]>>[Br:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[O:7][CH2:8][CH2:9][O:10]2)[cH:11][cH:12]1
O=Cc1ccc(Br)cc1.OCCO
Brc1ccc(C2OCCO2)cc1
null
null
C(C)(=O)OCC.C1=CC=CC=C1
Heteroatom Alkylation and Arylation
OtherReaction
fe0fbb45a87f24c1e456c6b4e41101562cd8f0af3ec376bb6115e7c1555d997b
7ac65b5a5f576337ce8e86e0130eb9b4757ca21b2419a0e82bbdfd5def30ee73
c1ccc(C2OCCO2)cc1
O-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3].[O;H0;D1;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[CH;D3;+0:5]1-[O;H0;D2;+0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-1):[c:8]
null
[]
null
null
3
HOUR
4-Bromobenzaldehyde (3 g, 0.0162 mol) in benzene (60 mL) was treated with p-toluenesulfonic acid monohydrate (0.15 g, 0.79 mmol) and ethylene glycol (5 mL, 0.0896 mol). The reaction was refluxed under nitrogen with azeotropic removal of water. After 3 hours, the reaction was cooled to room temperature and diluted with ...
10.6084/m9.figshare.5104873.v1
null
Aldehyde.Primary alcohol.Primary alcohol
Ether.Ether
null
C1COCO1
c1ccccc1.C1COCO1
HO-
C(C)(=O)OCC.C1=CC=CC=C1
null
3
O=Cc1ccc(Br)cc1.OCCO>C(C)(=O)OCC.C1=CC=CC=C1>Brc1ccc(C2OCCO2)cc1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-bee7a5bb378040a9ab29ac748036e612
CO.O=C1Nc2ccccc2C1=O>>O=C1C(=O)N(c2ccc(C3OC=CO3)cc2)c2ccccc21
CO.[H-].[Na+].N1C(=O)C(=O)C2=CC=CC=C12>>O1C(OC=C1)C1=CC=C(C=C1)N1C(=O)C(=O)C2=CC=CC=C12
[CH3:10][OH:14].[O:1]=[C:2]1[C:3](=[O:4])[NH:5][c:17]2[cH:18][cH:6][cH:20][cH:21][c:22]21>>[O:1]=[C:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][cH:8][c:9]([CH:10]3[O:11][CH:12]=[CH:13][O:14]3)[cH:15][cH:16]2)[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21
CO.O=C1Nc2ccccc2C1=O
O=C1C(=O)N(c2ccc(C3OC=CO3)cc2)c2ccccc21
null
[Cu]I
C(Cl)(Cl)Cl.CN(C)C=O
Aromatic Heterocycle Formation
OtherReaction
7a1c0dfb868b85468c3a84d0bbdd5aa786abf31a9ea8c840ba9107a579f9db64
d49c64587a28d943ce63f48ec4984e46f0c42996321d9c2a4e005ed4e5bd0e26
O=C1C(=O)N(c2ccc(C3OC=CO3)cc2)c2ccccc21
[CH3;D1;+0:1]-[OH;D1;+0:2].[O;D1;H0:3]=[C:4]1-[C:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[c:8]2:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[c:12]:[c:13]:2-1>>[O;D1;H0:3]=[C:4]1-[C:5](=[O;D1;H0:6])-[N;H0;D3;+0:7](-[c;H0;D3;+0:10]2:[c:14]:[c:15]:[c:16](-[CH;D3;+0:1]3-[#8:17]-[C:18]=[C:19]-[O;H0;D2;+0:2]-3):[c:20]:[c:21]:2)-[c:8]2:[c...
null
[]
null
null
1
HOUR
Isatin (1.88 g, 0.0128 mol) in anhydrous DMF (100 mL) was cooled in an ice-bath under nitrogen and treated with sodium hydride (0.3 g, 1 equivalent). The reaction was warmed to room temperature and stirred for 1 hour. It was then treated with 2-(4-bromophenyl)-1,3-dioxalane (2.83 g, 0.0124 mol) followed by CuI (4.71 g,...
10.6084/m9.figshare.5104873.v1
null
Secondary amide.Methanol
Ether.Ether.Tertiary amide
c1ccc2c(c1)CCN2
c1ccccc1.C1=COCO1.c1ccc2c(c1)CC[NH]2
c1ccccc1.C1=COCO1.c1ccc2c(c1)CC[NH]2
Other
[Cu]I.C(Cl)(Cl)Cl.CN(C)C=O
null
1
CO.O=C1Nc2ccccc2C1=O>[Cu]I.C(Cl)(Cl)Cl.CN(C)C=O>O=C1C(=O)N(c2ccc(C3OC=CO3)cc2)c2ccccc21
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-9d1d916dbb9740ceb7e832ab900fa980
Brc1cccc(-c2ccc(OCc3ccccc3)cc2)c1.O=C1Nc2ccccc2C1=O>>O=C1C(=O)N(c2cccc(-c3ccc(OCc4ccccc4)cc3)c2)c2ccccc21
N1C(=O)C(=O)C2=CC=CC=C12.[H-].[Na+].C(C1=CC=CC=C1)OC1=CC=C(C=C1)C1=CC(=CC=C1)Br>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)C=1C=C(C=CC1)N1C(=O)C(=O)C2=CC=CC=C12
Br[c:6]1[cH:7][cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[cH:23][cH:24]2)[cH:25]1.[O:1]=[C:2]1[C:3](=[O:4])[NH:5][c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]21>>[O:1]=[C:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([O:15][C...
Brc1cccc(-c2ccc(OCc3ccccc3)cc2)c1.O=C1Nc2ccccc2C1=O
O=C1C(=O)N(c2cccc(-c3ccc(OCc4ccccc4)cc3)c2)c2ccccc21
null
[Cu](I)I
CN(C)C=O
Heteroatom Alkylation and Arylation
Goldberg coupling
a6140d1302c1424aae9fd07d1a1cdfb4f8078cc053096587236f0e3c31860bdd
e3642f27d4c4bc101b8817e43c6aa5a22f60531030ee51c1c76056fd17c8df37
O=C1C(=O)N(c2cccc(-c3ccc(OCc4ccccc4)cc3)c2)c2ccccc21
Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;D1;H0:6]=[C:7]1-[c:8]:[c:9](:[c:10])-[NH;D2;+0:11]-[C:12]-1=[O;D1;H0:13]>>[O;D1;H0:6]=[C:7]1-[c:8]:[c:9](:[c:10])-[N;H0;D3;+0:11](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:12]-1=[O;D1;H0:13]
null
[]
null
null
0.5
HOUR
Isatin (0.12 g, 0.81 mmol) in anhydrous DMF (30 mL) was cooled in an ice-bath under nitrogen and treated with sodium hydride (21 mg, 1.1 equivalents). The reaction was stirred in ice for 0.5 hours and then warmed to room temperature. This solution was then treated with 4-(3-bromophenyl)phenol benzyl ether (Hajduk et al...
10.6084/m9.figshare.5104873.v1
null
Aromatic halide.Secondary amide
Tertiary amide
c1ccccc1.c1ccc2c(c1)CCN2
c1ccccc1.c1ccc2c(c1)CC[NH]2
c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2c(c1)CC[NH]2
HBr
[Cu](I)I.CN(C)C=O
null
0.5
Brc1cccc(-c2ccc(OCc3ccccc3)cc2)c1.O=C1Nc2ccccc2C1=O>[Cu](I)I.CN(C)C=O>O=C1C(=O)N(c2cccc(-c3ccc(OCc4ccccc4)cc3)c2)c2ccccc21
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-a1b2d0e683464eb585672bec5e4b02fc
COCCOCCl.Oc1ccc(I)cc1>>COCCOCOc1ccc(I)cc1
CCOCC.COCCOCCl.IC1=CC=C(C=C1)O.[H-].[Na+]>>COCCOCOC1=CC=C(C=C1)I
Cl[CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1].[OH:7][c:8]1[cH:9][cH:10][c:11]([I:12])[cH:13][cH:14]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([I:12])[cH:13][cH:14]1
COCCOCCl.Oc1ccc(I)cc1
COCCOCOc1ccc(I)cc1
null
null
O1CCCC1
Heteroatom Alkylation and Arylation
Williamson Ether Synthesis
6e90ffbf0683e1a3ee55c5e3ea453aefc5ddd369c0150ed0150f9546d7e47f4f
efd670663709b79afcad1306da9f69b33a0147cfa3639ca4c0b54b35ef4b1852
c1ccccc1
Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]
null
[]
0
CELSIUS
30
MINUTE
A solution of 4-iodophenol (10 g, 45.45 mmol) in 200 ml of anhydrous tetrahydrofuran was treated at 0° C. with sodium hydride (2.36 g, 60% dispersion, 59.09 mmol) for 5 minutes. To the resulting mixture was slowly added over a 5-minute period methoxyethoxymethyl chloride (8.3 ml, 72.73 mmol). The mixture was stirred at...
10.6084/m9.figshare.5104873.v1
null
Primary halide.Ether.Aromatic alcohol
Ether.Ether
null
null
c1ccccc1
HCl
O1CCCC1
0
0.5
COCCOCCl.Oc1ccc(I)cc1>O1CCCC1>COCCOCOc1ccc(I)cc1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-b168db1e34b1403f93a8212f0332cfb6
C=CCCCCC(C)[Si](C)(C)Cl.O>>C=CCCCCC(C)[Si](C)(C)O
C=CCCCCC(C)[Si](Cl)(C)C.C(C)N(CC)CC.O>>C=CCCCCC(C)[Si](O)(C)C
Cl[Si:9]([CH:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1])[CH3:8])([CH3:10])[CH3:11].[OH2:12]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([CH3:8])[Si:9]([CH3:10])([CH3:11])[OH:12]
C=CCCCCC(C)[Si](C)(C)Cl.O
C=CCCCCC(C)[Si](C)(C)O
null
null
CCOCC
Protection
OtherReaction
8fcc4c3cc9b76ad7a25dadc60c2bf40d0808fa925288f755ee2252a082747b94
f0dce65f75d702dc7e016c0abdb24b26134ae5c509e2d0da4a21967fb59ed09d
null
Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C:5])-[C;D1;H3:6].[OH2;D0;+0:7]>>[C:5]-[C:4](-[C;D1;H3:6])-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[OH;D1;+0:7]
null
[]
null
null
null
null
A solution of 7-oct-1-enyldimethylchlorosilane (2.56 ml) in ether (2 ml) was added dropwise over 1 hour to a stirring mixture of triethylamine (1.5 ml), water (0.18 ml) and ether (15 ml) in an ice/water bath. The resultant was stirred a further 1 hour in the ice/water bath and filtered washing the filtered solid with e...
10.6084/m9.figshare.5104873.v1
null
Silyl protective group
Silyl protective group
null
null
null
HCl
CCOCC
null
null
C=CCCCCC(C)[Si](C)(C)Cl.O>CCOCC>C=CCCCCC(C)[Si](C)(C)O
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-fe9f5420bfd84270b08f39e9fa9c1dc5
N#CC1C(C#N)C2(c3ccccc3)OC1(c1ccccc1)C1=CC=CCC12>>N#Cc1c(C#N)c(-c2ccccc2)c2ccccc2c1-c1ccccc1
C1(=CC=CC=C1)C12C(C(C(C3CC=CC=C13)(O2)C2=CC=CC=C2)C#N)C#N>>C1(=CC=CC=C1)C1=C(C(=C(C2=CC=CC=C12)C1=CC=CC=C1)C#N)C#N
O1[C:7]2([c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[CH:4]([C:5]#[N:6])[CH:3]([C:2]#[N:1])[C:20]1([c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[C:19]1=[CH:18][CH:17]=[CH:16][CH2:15][CH:14]21>>[N:1]#[C:2][c:3]1[c:4]([C:5]#[N:6])[c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[c:2...
N#CC1C(C#N)C2(c3ccccc3)OC1(c1ccccc1)C1=CC=CCC12
N#Cc1c(C#N)c(-c2ccccc2)c2ccccc2c1-c1ccccc1
null
null
O1CCCC1
Functional Group Interconversion
OtherReaction
451ce399a9975a2e24721bfe746f28195e80d674d8620ca7846ce01aed2fdc0d
ba1a6c29f1bb13cb6b068c6404f329154f930fd1862f573c00b21c416075f08b
c1ccc(-c2ccc(-c3ccccc3)c3ccccc23)cc1
[N;D1;H0:1]#[C:2]-[CH;D3;+0:3]1-[CH;D3;+0:4](-[C:5]#[N;D1;H0:6])-[C;H0;D4;+0:7]2(-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12])-O-[C;H0;D4;+0:13]-1(-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18])-[C;H0;D3;+0:19]1=[CH;D2;+0:20]-[CH;D2;+0:21]=[CH;D2;+0:22]-[CH2;D2;+0:23]-[CH;D3;+0:24]-1-2>>[N;D1;H0:1]#[C:2]-[c;H0;D3;+0:3]...
null
[]
-78
CELSIUS
20
MINUTE
In a dry 2 L 3-necked round bottom flask equipped with a magnetic stirring bar, dropping funnel, gas inlet tube attached to an argon gas cylinder, was placed tetrahydro-1,4-diphenyl-1,4-epoxy-napthalene-2,3-dicarbonitrile (20 g) and dry tetrahydrofuran (450 ml) while purging the flask with argon gas. The mixture was st...
10.6084/m9.figshare.5104873.v1
null
Ether.Conjugated diene
null
C1=CCC2C(=C1)C1CCC2O1
c1ccc2ccccc2c1
c1ccccc1.c1ccc2ccccc2c1.c1ccccc1
HO-
O1CCCC1
-78
0.333333
N#CC1C(C#N)C2(c3ccccc3)OC1(c1ccccc1)C1=CC=CCC12>O1CCCC1>N#Cc1c(C#N)c(-c2ccccc2)c2ccccc2c1-c1ccccc1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-3738a08b44d94a08965d8d835f3e0960
C=CC(=O)OCC.CCC1CC(O)C(=O)O1>>C/C=C/C=C/C(=O)OCC
C(C=C)(=O)OCC.OC(C(=O)OCC)CC(CC)O.C(C)C1CC(C(=O)O1)O>>C(\C=C\C=C\C)(=O)OCC
[CH2:4]=[CH:5][C:6](=[O:7])[O:8][CH2:9][CH3:10].O=C1O[CH:3]([CH2:2][CH3:1])CC1O>>[CH3:1]/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[C:6](=[O:7])[O:8][CH2:9][CH3:10]
C=CC(=O)OCC.CCC1CC(O)C(=O)O1
C/C=C/C=C/C(=O)OCC
null
null
C(CC)O
C-C Coupling
OtherReaction
05863aa458dfdd2f9a9c8e48495557f87e213b999a473b9142023c9077383b70
94bc7d13335f648a028b25b9386071a96909b7b4bc887b60ca6df890b110e0fe
null
O-C1-C-[CH;D3;+0:1](-[CH2;D2;+0:2]-[C;D1;H3:3])-O-C-1=O.[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]=[CH2;D1;+0:9]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])/[C:8]=[CH;D2;+0:9]/[CH;D2;+0:1]=[CH;D2;+0:2]/[C;D1;H3:3]
null
[]
null
null
null
null
For example, when n-propyl alcohol is allowed to react with ethyl acrylate, ethyl 2,4-dihydroxyhexanoate corresponding to Formula (4) and 4-ethyl-2-hydroxy-γ-butyrolactone corresponding to Formula (6) are formed under some conditions in addition to the target ethyl sorbate. Conditions: See reaction.notes.procedure_deta...
10.6084/m9.figshare.5104873.v1
null
Ester.Secondary alcohol.Vinyl
Conjugated diene
C1CCOC1
null
null
HO-
C(CC)O
null
null
C=CC(=O)OCC.CCC1CC(O)C(=O)O1>C(CC)O>C/C=C/C=C/C(=O)OCC
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-809c0d72a74341ac83c5e978963cd374
NO.O=C1OC(=O)c2cccc3cccc1c23>>O=C1c2cccc3cccc(c23)C(=O)N1O
Cl.NO.C12=CC=CC3=CC=CC(=C13)C(=O)OC2=O>>C1=CC2=C3C(=C1)C(=O)N(C(=O)C3=CC=C2)O
[NH2:15][OH:16].O1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][c:7]3[cH:8][cH:9][cH:10][c:11]([c:12]23)[C:13]1=[O:14]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][c:7]3[cH:8][cH:9][cH:10][c:11]([c:12]23)[C:13](=[O:14])[N:15]1[OH:16]
NO.O=C1OC(=O)c2cccc3cccc1c23
O=C1c2cccc3cccc(c23)C(=O)N1O
null
null
N1=CC=CC=C1
Acylation
OtherReaction
5aba1dbad83d843f1ecd19c79e2bc937b3e208ad1dbc10fd95a15f3af4c53c65
d977f6b45d8490a792c6b55d337372179d32e3e590a2ec2a2038b22791d10875
O=C1NC(=O)c2cccc3cccc1c23
[NH2;D1;+0:1]-[O;D1;H1:2].[O;D1;H0:3]=[C;H0;D3;+0:4]1-O-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c:9]:[c:10]-1:[c:11]>>[O;D1;H0:3]=[C;H0;D3;+0:4]1-[N;H0;D3;+0:1](-[O;D1;H1:2])-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c:9]:[c:10]-1:[c:11]
81
[{"value": 81.0, "product": "C1=CC2=C3C(=C1)C(=O)N(C(=O)C3=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.9, "product": "C1=CC2=C3C(=C1)C(=O)N(C(=O)C3=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}]
40
CELSIUS
null
null
A 3-L flask equipped with a stirrer, cooling tube and thermometer was purged by nitrogen gas. 55.2 g (770 mmol) of hydroxylamine-hydrochloride (purity of 97%) and 1.2 L of pyridine were added to the flask and were stirred to dissolve at room temperature under nitrogen atmosphere. To the stirred mixture, 138.7 g (700 mm...
10.6084/m9.figshare.5104873.v1
null
Anhydride.Ester.Ester.Primary amine
Tertiary amide.Tertiary amide
c1cc2c3c(cccc3c1)COC2
c1cc2c3c(cccc3c1)C[NH]C2
c1cc2c3c(cccc3c1)C[NH]C2
HO-
N1=CC=CC=C1
40
null
NO.O=C1OC(=O)c2cccc3cccc1c23>N1=CC=CC=C1>O=C1c2cccc3cccc(c23)C(=O)N1O
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-c0445d05ab4f429cb3885bb541566ec9
CCOC(=O)C1CCCCN1C>>CN1CCCCC1C(=O)O
C(C)OC(=O)C1N(CCCC1)C.[OH-].[Na+].Cl>>CN1C(CCCC1)C(=O)O
CC[O:10][C:8]([CH:7]1[N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6]1)=[O:9]>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[C:8](=[O:9])[OH:10]
CCOC(=O)C1CCCCN1C
CN1CCCCC1C(=O)O
null
null
CO.O
Deprotection
Ester saponification (alkyl deprotection)
d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894
38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9
C1CCNCC1
C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]>>[#7:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]
null
[]
null
null
8
HOUR
N-Methyl-piperidine-2-carboxylic acid ethyl ester (5.1 g) was dissolved in a mixture of 100 ml methanol and 10 ml water. NaOH (8 g) was added and the reaction mixture was stirred at room temperature overnight. The solution was then neutralized with hydrochloric acid, evaporated to dryness, and evaporated four times wit...
10.6084/m9.figshare.5104873.v1
null
Ester
Carboxylic acid
null
null
C1CC[NH]CC1
Other
CO.O
null
8
CCOC(=O)C1CCCCN1C>CO.O>CN1CCCCC1C(=O)O
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-71d5c1e5a135455fba4054b6175a1d2a
CC(C)[C@H](N)C(=O)N(C)[C@H](C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCc1ccccc1)C(C)C.O=C(O)[C@H]1CCCN1C(=O)OCc1ccccc1>>CC(C)[C@H](NC(=O)[C@H]1CCCN1C(=O)OCc1ccccc1)C(=O)N(C)[C@H](C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCc1ccccc1)C(C)C
C(C)N(CC)CC.N1([C@@H](C(=O)O)CCC1)C(=O)OCC1=CC=CC=C1.N[C@@H](C(C)C)C(=O)N([C@@H](C(C)C)C(=O)N1[C@H](C(=O)N2[C@H](C(=O)NCC3=CC=CC=C3)CCC2)CCC1)C.Cl>>N1([C@@H](C(=O)N[C@@H](C(C)C)C(=O)N([C@@H](C(C)C)C(=O)N2[C@H](C(=O)N3[C@H](C(=O)NCC4=CC=CC=C4)CCC3)CCC2)C)CCC1)C(=O)OCC1=CC=CC=C1
[CH3:1][CH:2]([CH3:3])[C@H:4]([NH2:5])[C:23](=[O:24])[N:25]([CH3:26])[C@H:27]([C:28](=[O:29])[N:30]1[CH2:31][CH2:32][CH2:33][C@H:34]1[C:35](=[O:36])[N:37]1[CH2:38][CH2:39][CH2:40][C@H:41]1[C:42](=[O:43])[NH:44][CH2:45][c:46]1[cH:47][cH:48][cH:49][cH:50][cH:51]1)[CH:52]([CH3:53])[CH3:54].O[C:6](=[O:7])[C@H:8]1[CH2:9][CH...
CC(C)[C@H](N)C(=O)N(C)[C@H](C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCc1ccccc1)C(C)C.O=C(O)[C@H]1CCCN1C(=O)OCc1ccccc1
CC(C)[C@H](NC(=O)[C@H]1CCCN1C(=O)OCc1ccccc1)C(=O)N(C)[C@H](C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCc1ccccc1)C(C)C
null
null
CN(C)C=O
Acylation
Carboxylic acid with primary amine to amide
37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8
1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4
O=C(CNC(=O)[C@H]1CCCN1C(=O)OCc1ccccc1)NCC(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCc1ccccc1
O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[C:6](-[#8:7])=[O;D1;H0:8])-[C:9].[#7:10]-[C:11](=[O;D1;H0:12])-[C:13]-[#7:14](-[C;D1;H3:15])-[C:16](=[O;D1;H0:17])-[C:18](-[C:19])-[NH2;D1;+0:20]>>[#7:10]-[C:11](=[O;D1;H0:12])-[C:13]-[#7:14](-[C;D1;H3:15])-[C:16](=[O;D1;H0:17])-[C:18](-[C:19])-[NH;D2;+0:20]-[C;H0;D...
null
[]
0
CELSIUS
8
HOUR
3.74 g Z-D-Pro-OH (15 mmol, BACHEM) and 8.25 g H-Val-MeVal-Pro-Pro-NHBn×HCl (15 mmol) were dissolved in 80 ml dry DMF. After cooling to 0° C., 2.4 g DEPCN (2.25 ml, 15 mmol) and 4.2 ml triethylamine (30 mmol) were added. The reaction mixture was stirred at 0° C. for several hours and room temperature overnight, then th...
10.6084/m9.figshare.5104873.v1
null
Carboxylic acid.Primary amine
Secondary amide
null
null
C1CC[NH]C1.c1ccccc1.C1CC[NH]C1.C1CC[NH]C1.c1ccccc1
HO-
CN(C)C=O
0
8
CC(C)[C@H](N)C(=O)N(C)[C@H](C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCc1ccccc1)C(C)C.O=C(O)[C@H]1CCCN1C(=O)OCc1ccccc1>CN(C)C=O>CC(C)[C@H](NC(=O)[C@H]1CCCN1C(=O)OCc1ccccc1)C(=O)N(C)[C@H](C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCc1ccccc1)C(C)C
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-6d6f150a18ea41f783d9bece53d51bab
CC[C@H](C)[C@H](NC(=O)[C@@H]1CCCN1C(=O)OC(C)(C)C)C(=O)O>>CC[C@H](C)[C@H](NC(=O)[C@@H]1CCCN1)C(=O)O
C1(CCCCC1)N=C=NC1CCCCC1.N1([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)O)CCC1)C(=O)OC(C)(C)C.ON1N=NC2=C1C=CC=C2.S1CNCC1>>N1[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)O)CCC1
CC(C)(C)OC(=O)[N:13]1[C@H:9]([C:7]([NH:6][C@@H:5]([C@H:3]([CH2:2][CH3:1])[CH3:4])[C:14](=[O:15])[OH:16])=[O:8])[CH2:10][CH2:11][CH2:12]1>>[CH3:1][CH2:2][C@H:3]([CH3:4])[C@H:5]([NH:6][C:7](=[O:8])[C@@H:9]1[CH2:10][CH2:11][CH2:12][NH:13]1)[C:14](=[O:15])[OH:16]
CC[C@H](C)[C@H](NC(=O)[C@@H]1CCCN1C(=O)OC(C)(C)C)C(=O)O
CC[C@H](C)[C@H](NC(=O)[C@@H]1CCCN1)C(=O)O
null
null
ClCCl.C(C)(=O)OCC
Reduction
Boc amine deprotection
7b506000be0005f6be41b2386b5bd6a8c45f704baa22d692d2f2ec984758e4ad
a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd
C1CCNC1
C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C:6](=[O;D1;H0:7])-[#7:8]-[C:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]>>[O;D1;H0:11]=[C:10](-[O;D1;H1:12])-[C:9]-[#7:8]-[C:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1
80
[{"value": 80.0, "product": "N1[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)O)CCC1", "details": "PERCENTYIELD", "is_desired": false}]
null
null
8
HOUR
6.5 mM Boc-Pro-Ile-OH (one equivalent=1 eq.) is suspended, together with N-hydroxybenzotriazole (1 eq.) and thiazolidine (1 eq.), in 30 ml of dichloromethane (DCM). The equivalent amount of 1M dicyclohexylcarbodiimide solution is added dropwise, at −10° C., with stirring. Stirring is carried out at −10° C. and overnigh...
10.6084/m9.figshare.5104873.v1
null
Carbamic ester.Ether.Boc
Secondary amine
C1CC[NH]C1
C1CCNC1
C1CCNC1
HO-
ClCCl.C(C)(=O)OCC
null
8
CC[C@H](C)[C@H](NC(=O)[C@@H]1CCCN1C(=O)OC(C)(C)C)C(=O)O>ClCCl.C(C)(=O)OCC>CC[C@H](C)[C@H](NC(=O)[C@@H]1CCCN1)C(=O)O
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-c8f6b1efb67c40169e37903c1c1b24ce
O=P([O-])([O-])OC1C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C1OP(=O)([O-])[O-]>>OC1C(O)C(O)C(O)C(O)C1O
C1(C(C(C(C(C1OP(=O)([O-])[O-])OP(=O)([O-])[O-])OP(=O)([O-])[O-])OP(=O)([O-])[O-])OP(=O)([O-])[O-])OP(=O)([O-])[O-].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].N1=CC=CC=C1>>C1(C(C(C(C(C1O)O)O)O)O)O
O=P([O-])([O-])[O:1][CH:2]1[CH:3]([O:4]P(=O)([O-])[O-])[CH:5]([O:6]P(=O)([O-])[O-])[CH:7]([O:8]P(=O)([O-])[O-])[CH:9]([O:10]P(=O)([O-])[O-])[CH:11]1[O:12]P(=O)([O-])[O-]>>[OH:1][CH:2]1[CH:3]([OH:4])[CH:5]([OH:6])[CH:7]([OH:8])[CH:9]([OH:10])[CH:11]1[OH:12]
O=P([O-])([O-])OC1C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C1OP(=O)([O-])[O-]
OC1C(O)C(O)C(O)C(O)C1O
null
null
O
Reduction
OtherReaction
9f5cad772b54d14041d2a94a56c7517d1e9be91b1f69e668338ff1d9057416a3
8e9eafa7bcb55b5783e579e184b7639878a9778db5bdde6fd8dfe3424695d74a
C1CCCCC1
O=P(-[O-])(-[O-])-[O;H0;D2;+0:1]-[C:2]1-[C:3](-[O;H0;D2;+0:4]-P(=O)(-[O-])-[O-])-[C:5](-[O;H0;D2;+0:6]-P(=O)(-[O-])-[O-])-[C:7](-[O;H0;D2;+0:8]-P(=O)(-[O-])-[O-])-[C:9](-[O;H0;D2;+0:10]-P(=O)(-[O-])-[O-])-[C:11]-1-[O;H0;D2;+0:12]-P(=O)(-[O-])-[O-]>>[OH;D1;+0:1]-[C:2]1-[C:3](-[OH;D1;+0:4])-[C:5](-[OH;D1;+0:6])-[C:7](-[O...
null
[]
65
CELSIUS
null
null
Crystalline sodium phytate C (4 g) was dissolved with sonication in water (20 ml) and converted to the free acid by passage through a column of Dowex 50x8-200 ion-exchange resign. The column eluate was adjusted to pH 8 with pyridine and evaporated to dryness. The residue was dissolved in water (30 ml) and pyridine (130...
10.6084/m9.figshare.5104873.v1
null
null
Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol
null
null
C1CCCCC1
Other
O
65
null
O=P([O-])([O-])OC1C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C(OP(=O)([O-])[O-])C1OP(=O)([O-])[O-]>O>OC1C(O)C(O)C(O)C(O)C1O
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-646d3ea39fc742a58d39c04413db354d
ClCc1ccccc1.OCCOCCOCCOCCOCCOCCO>>OCCOCCOCCOCCOCCOCCOCc1ccccc1
C(C1=CC=CC=C1)Cl.[OH-].[Na+].[OH-].[Na+].C(COCCOCCOCCOCCOCCO)O>>C(C1=CC=CC=C1)OCCOCCOCCOCCOCCOCCO
Cl[CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1.[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][OH:19]>>[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH...
ClCc1ccccc1.OCCOCCOCCOCCOCCOCCO
OCCOCCOCCOCCOCCOCCOCc1ccccc1
null
null
O.[Cl-].[Na+].O
Heteroatom Alkylation and Arylation
Williamson Ether Synthesis
dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c
46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca
c1ccccc1
Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]
null
[]
100
CELSIUS
18
HOUR
An aqueous sodium hydroxide solution prepared by dissolving 3.99 g (100 mmol) NaOH in 4 ml water was added slowly to non-polydispersed hexaethylene glycol (28.175 g, 25 ml, 100 mmol). Benzyl chloride (3.9 g, 30.8 mmol, 3.54 ml) was added and the reaction mixture was heated with stirring to 100° C. for 18 hours. The rea...
10.6084/m9.figshare.5104873.v1
null
Primary halide.Primary alcohol
Ether
null
null
c1ccccc1
HCl
O.[Cl-].[Na+].O
100
18
ClCc1ccccc1.OCCOCCOCCOCCOCCOCCO>O.[Cl-].[Na+].O>OCCOCCOCCOCCOCCOCCOCc1ccccc1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-56709f79ec1b4bf9ab722fd853d666a5
CCOC(=O)CCCCCO.CS(=O)(=O)Cl>>CCOC(=O)CCCCCOS(C)(=O)=O
C(C)N(CC)CC.OCCCCCC(=O)OCC.CS(=O)(=O)Cl>>CS(=O)(=O)OCCCCCC(=O)OCC
[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].Cl[S:12]([CH3:13])(=[O:14])=[O:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][S:12]([CH3:13])(=[O:14])=[O:15]
CCOC(=O)CCCCCO.CS(=O)(=O)Cl
CCOC(=O)CCCCCOS(C)(=O)=O
null
null
ClCCl
Acylation
Formation of Sulfonic Esters
2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf
cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a
null
Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4]
85.3
[{"value": 85.0, "product": "CS(=O)(=O)OCCCCCC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.3, "product": "CS(=O)(=O)OCCCCCC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}]
null
null
null
null
A solution of non-polydispersed ethyl 6-hydroxyhexanoate (50.76 ml, 50.41 g, 227 mmol) in dry dichloromethane (75 ml) was chilled in a ice bath and placed under a nitrogen atmosphere. Triethylamine (34.43 ml, 24.99 g, 247 mmol) was added. A solution of methanesulfonyl chloride (19.15 ml, 28.3 g, 247 mmol) in dry dichlo...
10.6084/m9.figshare.5104873.v1
null
Primary alcohol.Sulfonyl halide
Mesylate
null
null
null
HCl
ClCCl
null
null
CCOC(=O)CCCCCO.CS(=O)(=O)Cl>ClCCl>CCOC(=O)CCCCCOS(C)(=O)=O
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-22779d9b09bf45578601fa99ed994e05
CCOC(=O)CCCCCOS(C)(=O)=O.OCCOCCOCCOCCOCCOCCOCc1ccccc1>>CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCc1ccccc1
CS(=O)(=O)OCCCCCC(=O)OCC.[H-].[Na+].C(C1=CC=CC=C1)OCCOCCOCCOCCOCCOCCO.[H-].[Na+]>>C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCOCC1=CC=CC=C1)=O
CS(=O)(=O)O[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][C...
CCOC(=O)CCCCCOS(C)(=O)=O.OCCOCCOCCOCCOCCOCCOCc1ccccc1
CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCc1ccccc1
null
null
C1(=CC=CC=C1)C
Heteroatom Alkylation and Arylation
OtherReaction
5c62be0c00207c22aa0b4ea40c3bc578847f280a3c2710713116f1e5286da21f
f5cafe2a44880b31731a61404bce855c60bfa52affda0d60b208bb5279cadd5b
c1ccccc1
C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3]
44
[{"value": 44.0, "product": "C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCOCC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.8, "product": "C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCOCC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}]
0
CELSIUS
null
null
Sodium hydride (3.225 g or a 60% oil dispersion, 80.6 mmol) was suspended in 80 ml of anhydrous toluene, placed under a nitrogen atmosphere and cooled in an ice bath. A solution of the non-polydispersed alcohol 16 (27.3 g, 73.3 mmol) in 80 ml dry toluene was added to the NaH suspension. The mixture was stirred at 0° C....
10.6084/m9.figshare.5104873.v1
null
Mesylate.Primary alcohol
Ether
null
null
c1ccccc1
MsOH.HO-
C1(=CC=CC=C1)C
0
null
CCOC(=O)CCCCCOS(C)(=O)=O.OCCOCCOCCOCCOCCOCCOCc1ccccc1>C1(=CC=CC=C1)C>CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCc1ccccc1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-baeec4a04db444d58f3d0e5cdc22f086
CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCc1ccccc1>>CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCO
C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCOCC1=CC=CC=C1)=O>>C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCO)=O
c1ccc(C[O:29][CH2:28][CH2:27][O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])cc1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:...
CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCc1ccccc1
CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCO
null
[Pd]
C(C)O
Deprotection
Hydroxyl benzyl deprotection
c8a6fd2e05b2d36256c76b73aaf4118f20eb14abce1c0289b554265e30b218aa
29a81fd08d26edc3da6d72c4958026f5af2119326dc1b4714ee5be1c41835609
null
[C:1]-[C:2]-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2]-[OH;D1;+0:3]
79
[{"value": 79.0, "product": "C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCO)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.9, "product": "C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCO)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}]
null
null
4
HOUR
Non-polydispersed benzyl ether 18 (1.03 g, 2.0 mmol) was dissolved in 25 ml ethanol. To this solution was added 270 mg 10% Pd/C, and the mixture was placed under a hydrogen atmosphere and stirred for four hours, at which time TLC showed the complete disappearance of the starting material. The reaction mixture was filte...
10.6084/m9.figshare.5104873.v1
null
Ether
Primary alcohol
c1ccccc1
null
null
Other
[Pd].C(C)O
null
4
CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCc1ccccc1>[Pd].C(C)O>CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCO
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-52034d2574fc41df82c266c241c0c698
CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCO.CS(=O)(=O)Cl>>CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCS(C)(=O)=O
C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCO)=O.C(C)N(CC)CC.CS(=O)(=O)Cl>>C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCS(=O)(=O)C)=O
O[CH2:28][CH2:27][O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].Cl[S:29]([CH3:30])(=[O:31])=[O:32]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:12]...
CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCO.CS(=O)(=O)Cl
CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCS(C)(=O)=O
null
null
ClCCl
Acylation
OtherReaction
0ac8a603953c98c1814574689e0056190c62616c176b8b4c31c7acd96ef43528
7d02e147285bb417922c236d16ce79bf71b54bc3f6dc1c2237422f2069c2cc63
null
Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].O-[CH2;D2;+0:5]-[C:6]-[#8:7]>>[#8:7]-[C:6]-[CH2;D2;+0:5]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4]
85.4
[{"value": 83.0, "product": "C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCS(=O)(=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.4, "product": "C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCS(=O)(=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}]
0
CELSIUS
2
MINUTE
The non-polydispersed alcohol 19 (0.835 g, 1.97 mmol) was dissolved in 3.5 ml dry dichloromethane and placed under a nitrogen atmosphere. Triethylamine (0.301 ml, 0.219 g, 2.16 mmol) was added and the mixture was chilled in an ice bath. After two minutes, the methanesulfonyl chloride (0.16 ml, 0.248 g, 2.16 mmol) was a...
10.6084/m9.figshare.5104873.v1
null
Primary alcohol.Sulfonyl halide
Sulfone
null
null
null
HCl
ClCCl
0
0.033333
CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCO.CS(=O)(=O)Cl>ClCCl>CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCS(C)(=O)=O
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-4fa6ce2833494a9795e9d24918fc4a33
CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCS(C)(=O)=O.COCCOCCO>>CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCCOC
C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCS(=O)(=O)C)=O.[H-].[Na+].COCCOCCO>>C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCOCCOC)=O
CS(=O)(=O)CCO[CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10...
CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCS(C)(=O)=O.COCCOCCO
CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCCOC
null
null
C1(=CC=CC=C1)C
Heteroatom Alkylation and Arylation
OtherReaction
6d997269875377ef22a4c0d7efe65e0adbadca96f5ffe8e44c9a72e2d4e677ef
0ce75b19ae964881255ad90d79aea86c56b1e7de58d067a06f3fccfc3b5cadf6
null
C-S(=O)(=O)-C-C-O-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[C:5]-[C:4]
62.6
[{"value": 57.0, "product": "C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCOCCOC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.6, "product": "C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCOCCOC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}]
0
CELSIUS
4
HOUR
NaH (88 mg of a 60% dispersion in oil, 2.2 mmol) was suspended in anhydrous toluene (3 ml) under N2 and chilled to 0° C. Non-polydispersed diethylene glycol monomethyl ether (0.26 ml, 0.26 g, 2.2 mmol) that had been dried via azeotropic distillation with toluene was added. The reaction mixture was allowed to warm to ro...
10.6084/m9.figshare.5104873.v1
null
Ether.Primary alcohol.Sulfone
Ether
null
null
null
HO-
C1(=CC=CC=C1)C
0
4
CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCS(C)(=O)=O.COCCOCCO>C1(=CC=CC=C1)C>CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCCOC
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-4351b66e07de4148a6afa743ffeb6869
CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCCOC>>COCCOCCOCCOCCOCCOCCOCCOCCCCCC(=O)O
C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCOCCOC)=O>>COCCOCCOCCOCCOCCOCCOCCOCCCCCC(=O)O
CC[O:31][C:29]([CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])=[O:30]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH...
CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCCOC
COCCOCCOCCOCCOCCOCCOCCOCCCCCC(=O)O
null
null
[OH-].[Na+]
Deprotection
Ester saponification (alkyl deprotection)
d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894
38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9
null
C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1]
70.3
[{"value": 62.0, "product": "COCCOCCOCCOCCOCCOCCOCCOCCCCCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.3, "product": "COCCOCCOCCOCCOCCOCCOCCOCCCCCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}]
null
null
18
HOUR
Non-polydispersed ester 21 (0.25 g, 0.46 mmol) was stirred for 18 hours in 0.71 ml of 1 N NaOH. After 18 hours, the mixture was concentrated in vacuo to remove the alcohol and the residue dissolved in a further 10 ml of water. The aqueous solution was acidified to pH 2 with 2 N HCl and the product was extracted into di...
10.6084/m9.figshare.5104873.v1
null
Ester
Carboxylic acid
null
null
null
Other
[OH-].[Na+]
null
18
CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCCOC>[OH-].[Na+]>COCCOCCOCCOCCOCCOCCOCCOCCCCCC(=O)O
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-5d803043f8e6465ca587a6711981a4cf
CC(C)(C)[O-].OCCOCCOCCOCCO>>OCCOCCOCCOCCOCCOCCOCCO
C(COCCOCCOCCO)O.CC(C)([O-])C.[K+]>>C(COCCOCCOCCOCCOCCOCCO)O
[O-:1][C:2]([CH3:3])([CH3:6])[CH3:9].[OH:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][OH:22]>>[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][OH:22]
CC(C)(C)[O-].OCCOCCOCCOCCO
OCCOCCOCCOCCOCCOCCOCCO
null
null
C1CCOC1
Heteroatom Alkylation and Arylation
OtherReaction
019a2add4753736121b6b388a609e94cba6dcc60c916e684b025671623373b32
d043e4f411aa8a5a56c10984b753afb6b4605069dd72b1a070cd19012b179e21
null
[CH3;D1;+0:1]-[C;H0;D4;+0:2](-[CH3;D1;+0:3])(-[CH3;D1;+0:4])-[O-;H0;D1:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[CH2;D2;+0:4]-[C:9]-[#8:10]-[CH2;D2;+0:3]-[C:11]-[#8:12]-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[OH;D1;+0:5]
41
[{"value": 41.0, "product": "C(COCCOCCOCCOCCOCCOCCO)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.8, "product": "C(COCCOCCOCCOCCOCCOCCO)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}]
null
null
1
HOUR
To a solution of non-polydispersed tetraethylene glycol (51.5 g, 0.27 mol) in THF (1 L) was added potassium t-butoxide (14.8 g, 0.13 mol, small portions over ˜30 min). The reaction mixture was then stirred for 1 h and then 24 (29.15 g, 0.12 mol) dissolved in THF (90 mL) was added dropwise and the reaction mixture was s...
10.6084/m9.figshare.5104873.v1
null
Primary alcohol
Ether.Ether.Ether.Primary alcohol
null
null
null
null
C1CCOC1
null
1
CC(C)(C)[O-].OCCOCCOCCOCCO>C1CCOC1>OCCOCCOCCOCCOCCOCCOCCO
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-a1d63875a1484e9a87099c7b743dc497
ClCc1ccccc1.OCCOCCOCCOCCO>>OCCOCCOCCOCCOCc1ccccc1
C(COCCOCCOCCO)O.[OH-].[Na+].C(C1=CC=CC=C1)Cl>>C(C1=CC=CC=C1)OCCOCCOCCOCCO
Cl[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][OH:13]>>[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1
ClCc1ccccc1.OCCOCCOCCOCCO
OCCOCCOCCOCCOCc1ccccc1
null
null
[Na+].[Cl-]
Heteroatom Alkylation and Arylation
Williamson Ether Synthesis
dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c
46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca
c1ccccc1
Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]
71
[{"value": 71.0, "product": "C(C1=CC=CC=C1)OCCOCCOCCOCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.9, "product": "C(C1=CC=CC=C1)OCCOCCOCCOCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}]
100
CELSIUS
null
null
To the oil of non-polydispersed tetraethylene glycol (19.4 g, 0.10 mol) was added a solution of NaOH (4.0 g in 4.0 mL) and the reaction was stirred for 15 mm. Then benzyl chloride (3.54 mL, 30.8 mmol) was added and the reaction mixture was heated to 100° C. and stirred overnight. The reaction mixture was cooled to room...
10.6084/m9.figshare.5104873.v1
null
Primary halide.Primary alcohol
Ether
null
null
c1ccccc1
HCl
[Na+].[Cl-]
100
null
ClCc1ccccc1.OCCOCCOCCOCCO>[Na+].[Cl-]>OCCOCCOCCOCCOCc1ccccc1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-b2cbf350d667459bb6ec706b7b02f558
OCCOCCOCCOCCO.OCCOCCOCCOCCOCc1ccccc1>>OCCOCCOCCOCCOCCOCCOCCOCCOCc1ccccc1
[H-].[Na+].C(COCCOCCOCCO)O.S(C)(=O)(=O)[O-].C(C1=CC=CC=C1)OCCOCCOCCOCCO>>C(C1=CC=CC=C1)OCCOCCOCCOCCOCCOCCOCCOCCO
O[CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][OH:1].[OH:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1>>[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2...
OCCOCCOCCOCCO.OCCOCCOCCOCCOCc1ccccc1
OCCOCCOCCOCCOCCOCCOCCOCCOCc1ccccc1
null
null
O1CCCC1
Heteroatom Alkylation and Arylation
Alcohol to ether
812cd07f4ebd43f56ac542d53752263143ebee112e6268c60a96876bb9ae6b95
31a44c623e879cda50fc3ef399266dde4d5f7d364c38209e2960d8959326fbb0
c1ccccc1
O-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[C:5]-[C:4]
34.5
[{"value": 34.0, "product": "C(C1=CC=CC=C1)OCCOCCOCCOCCOCCOCCOCCOCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.5, "product": "C(C1=CC=CC=C1)OCCOCCOCCOCCOCCOCCOCCOCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}]
null
null
1
HOUR
To a solution of tetrahydrofuran (140 mL) containing sodium hydride (0.43 g, 18 mmol) was added dropwise a solution of non-polydispersed tetraethylene glycol (3.5 g, 18 mmol) in tetrahydrofuran (10 mL) and the reaction mixture was stirred for 1 h. Then mesylate of non-polydispersed tetraethylene glycol monobenzylether ...
10.6084/m9.figshare.5104873.v1
null
Primary alcohol.Primary alcohol
Ether
null
null
c1ccccc1
HO-
O1CCCC1
null
1
OCCOCCOCCOCCO.OCCOCCOCCOCCOCc1ccccc1>O1CCCC1>OCCOCCOCCOCCOCCOCCOCCOCCOCc1ccccc1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-30eb1584f3b64380bac531cfebd97b41
OCCOCCOCCO.OCCOCCOCCOCCOCCOCCO>>COCCOCCOCCOCCOCCOCCO
C(COCCOCCOCCOCCOCCO)O.C(=O)(Cl)Cl.C(COCCOCCO)O.C(=O)(Cl)Cl.C1(=CC=CC=C1)C>>COCCOCCOCCOCCOCCOCCO
[OH:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][OH:20].OCCOCCOCCO[CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][OH:2]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][OH:20]
OCCOCCOCCO.OCCOCCOCCOCCOCCOCCO
COCCOCCOCCOCCOCCOCCO
null
null
CCOC(=O)C
Heteroatom Alkylation and Arylation
OtherReaction
10f901834b998d67af93c14843d4ff9ef83fea029e2d7ebb1a7141118987c94c
d20b223689f1b397d568403780e4ac92290d10a44fac3bd5a5ecc93c0de7d4ca
null
O-C-C-O-C-C-O-C-C-O-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]-[OH;D1;+0:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[C:8]-[C:7].[C:4]-[C:5]-[O;H0;D2;+0:6]-[C;D1;H3:10]
null
[]
null
null
2.5
HOUR
The following description refers to the scheme illustrated in FIG. 10. Non-polydispersed activated hexaethylene glycol monomethyl ether was prepared analogously to that of non-polydispersed triethylene glycol in Example 39 above. A 20% phosgene in toluene solution (35 mL, 6.66 g, 67.4 mmol phosgene) was chilled under a...
10.6084/m9.figshare.5104873.v1
null
Ether.Ether.Ether.Primary alcohol.Primary alcohol.Primary alcohol
Ether.Ether
null
null
null
HO-
CCOC(=O)C
null
2.5
OCCOCCOCCO.OCCOCCOCCOCCOCCOCCO>CCOC(=O)C>COCCOCCOCCOCCOCCOCCO
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-c8f57662be2f41ff9d5b229abc5ecf44
CC(=O)c1c(OCc2ccccc2)cc(C)cc1OCc1ccccc1.O=Cc1ccc2ccccc2c1>>Cc1cc(O)c(C(=O)CCc2ccc3c(c2)CCCC3)c(O)c1
C(C1=CC=CC=C1)OC1=C(C(=CC(=C1)C)OCC1=CC=CC=C1)C(C)=O.C1=C(C=CC2=CC=CC=C12)C=O>>OC1=C(C(=CC(=C1)C)O)C(CCC1=CC=2CCCCC2C=C1)=O
c1ccc(C[O:5][c:4]2[cH:3][c:2]([CH3:1])[cH:23][c:21]([O:22]Cc3ccccc3)[c:6]2[C:7](=[O:8])[CH3:9])cc1.O=[CH:10][c:11]1[cH:12][cH:13][c:14]2[c:15]([cH:16]1)[cH:17][cH:18][cH:19][cH:20]2>>[CH3:1][c:2]1[cH:3][c:4]([OH:5])[c:6]([C:7](=[O:8])[CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14]3[c:15]([cH:16]2)[CH2:17][CH2:18][CH2:19][CH...
CC(=O)c1c(OCc2ccccc2)cc(C)cc1OCc1ccccc1.O=Cc1ccc2ccccc2c1
Cc1cc(O)c(C(=O)CCc2ccc3c(c2)CCCC3)c(O)c1
null
null
null
C-C Coupling
OtherReaction
a439652a13dde3282ba205540b7ed6f7cc5b9181cf04466803597623e6a23ce8
12f62631063bf464607920629837e3c85e8060bc45180357ec9dd6bf577ced50
O=C(CCc1ccc2c(c1)CCCC2)c1ccccc1
O=[CH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5]2:[cH;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:[c:10]:2:[c:11]:1.[CH3;D1;+0:12]-[C:13](=[O;D1;H0:14])-[c:15](:[c:16](-[O;H0;D2;+0:17]-C-c1:c:c:c:c:c:1):[c:18]):[c:19](-[O;H0;D2;+0:20]-C-c1:c:c:c:c:c:1):[c:21]>>[O;D1;H0:14]=[C:13](-[CH2;D2;+0:12]-[CH2;D2;+0:1]-[c:2]1:[c:3]:[...
null
[]
null
null
null
null
The intermediate, 1-(2,6-bis-benzyloxy-4-methyl-phenyl)-ethanone, was treated with 2-naphthaldehyde as described in Example 1, Part B. Subsequent catalytic hydrogenation as described in Example 1, Part C, provided 1-(2,6-Dihydroxy-4-methyl-phenyl)-3-(5,6,7,8-tetrahydro-naphthalen-2-yl)-propan-1-one as a by-product. Fur...
10.6084/m9.figshare.5104873.v1
null
Aldehyde.Ketone.Ether.Ether
Ketone.Aromatic alcohol.Aromatic alcohol
c1ccccc1.c1ccccc1.c1ccc2ccccc2c1
c1ccc2c(c1)CCCC2
c1ccccc1.c1ccc2c(c1)CCCC2
HO-
null
null
null
CC(=O)c1c(OCc2ccccc2)cc(C)cc1OCc1ccccc1.O=Cc1ccc2ccccc2c1>>Cc1cc(O)c(C(=O)CCc2ccc3c(c2)CCCC3)c(O)c1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-11331b076910446d825a7a20884c76ee
CC(=O)c1c(OCc2ccccc2)cc(C)cc1OCc1ccccc1.COc1ccc2cc(C=O)ccc2c1>>COC1CCc2cc(CCC(=O)c3c(O)cc(C)cc3O)ccc2C1
C(C1=CC=CC=C1)OC1=C(C(=CC(=C1)C)OCC1=CC=CC=C1)C(C)=O.COC=1C=C2C=CC(=CC2=CC1)C=O>>OC1=C(C(=CC(=C1)C)O)C(CCC1=CC=2CCC(CC2C=C1)OC)=O
c1ccc(C[O:15][c:14]2[c:13]([C:11]([CH3:10])=[O:12])[c:20]([O:21]Cc3ccccc3)[cH:19][c:17]([CH3:18])[cH:16]2)cc1.O=[CH:9][c:8]1[cH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:25][c:24]2[cH:23][cH:22]1>>[CH3:1][O:2][CH:3]1[CH2:4][CH2:5][c:6]2[cH:7][c:8]([CH2:9][CH2:10][C:11](=[O:12])[c:13]3[c:14]([OH:15])[cH:16][c:17]([CH3:...
CC(=O)c1c(OCc2ccccc2)cc(C)cc1OCc1ccccc1.COc1ccc2cc(C=O)ccc2c1
COC1CCc2cc(CCC(=O)c3c(O)cc(C)cc3O)ccc2C1
null
null
null
C-C Coupling
OtherReaction
1d74c26f0b54826bde53498c1b1ccad0c5ce09a5d28cb36902f3f9cebb72ee4d
50e927d848c47a415c1ffe91ec6f26ec0e8cee684590dd7a854ff7d46022aa7b
O=C(CCc1ccc2c(c1)CCCC2)c1ccccc1
O=[CH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5]2:[cH;D2;+0:6]:[c;H0;D3;+0:7](-[#8:8]-[C;D1;H3:9]):[cH;D2;+0:10]:[cH;D2;+0:11]:[c:12]:2:[c:13]:1.[CH3;D1;+0:14]-[C:15](=[O;D1;H0:16])-[c:17](:[c:18](-[O;H0;D2;+0:19]-C-c1:c:c:c:c:c:1):[c:20]):[c:21](-[O;H0;D2;+0:22]-C-c1:c:c:c:c:c:1):[c:23]>>[C;D1;H3:9]-[#8:8]-[CH;D3;+0:7]1-[CH2;D...
null
[]
null
null
null
null
Intermediate 1-(2,6-bis-benzyloxy-4-methyl-phenyl)-ethanone, was treated with 6-methoxynaphthalene-2-carbaldehyde as described in Example 1, Part B. Subsequent catalytic hydrogenation as described in Example 1, Part C, provided 1-(2,6-dihydroxy-4-methyl-phenyl)-3-(6-methoxy-5,6, 7,8-tetrahydro-naphthalen-2-yl)-propan-1...
10.6084/m9.figshare.5104873.v1
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Aldehyde.Ketone.Ether.Ether.Ether
Ketone.Ether.Aromatic alcohol.Aromatic alcohol
c1ccccc1.c1ccccc1.c1ccc2ccccc2c1
c1ccc2c(c1)CCCC2
c1ccc2c(c1)CCCC2.c1ccccc1
HO-
null
null
null
CC(=O)c1c(OCc2ccccc2)cc(C)cc1OCc1ccccc1.COc1ccc2cc(C=O)ccc2c1>>COC1CCc2cc(CCC(=O)c3c(O)cc(C)cc3O)ccc2C1
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d
ord-c6b8e2327e37440b8d9880a60b9b2f7a
ClCc1ccccc1.OCCOCCOCCOCCOCCOCCO>>OCCOCCOCCOCCOCCOCCOCc1ccccc1
C(C1=CC=CC=C1)Cl.[OH-].[Na+].[OH-].[Na+].C(COCCOCCOCCOCCOCCO)O>>C(C1=CC=CC=C1)OCCOCCOCCOCCOCCOCCO
Cl[CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1.[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][OH:19]>>[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH...
ClCc1ccccc1.OCCOCCOCCOCCOCCOCCO
OCCOCCOCCOCCOCCOCCOCc1ccccc1
null
null
O.[Cl-].[Na+].O
Heteroatom Alkylation and Arylation
Williamson Ether Synthesis
dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c
46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca
c1ccccc1
Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]
null
[]
100
CELSIUS
18
HOUR
An aqueous sodium hydroxide solution prepared by dissolving 3.99 g (100 mmol) NaOH in 4 ml water was added slowly to non-polydispersed hexaethylene glycol (28.175 g, 25 ml, 100 mmol). Benzyl chloride (3.9 g, 30.8 mmol, 3.54 ml) was added and the reaction mixture was heated with stirring to 100° C. for 18 hours. The rea...
10.6084/m9.figshare.5104873.v1
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Primary halide.Primary alcohol
Ether
null
null
c1ccccc1
HCl
O.[Cl-].[Na+].O
100
18
ClCc1ccccc1.OCCOCCOCCOCCOCCOCCO>O.[Cl-].[Na+].O>OCCOCCOCCOCCOCCOCCOCc1ccccc1