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molecular formula C22H25NO6 B118152 N-(1,2,3,10-Tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)acetamide CAS No. 209810-38-8

N-(1,2,3,10-Tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)acetamide

Cat. No. B118152
M. Wt: 399.4 g/mol
InChI Key: IAKHMKGGTNLKSZ-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US05426224

Procedure details

FIG. 6 illustrates how alternative colchine derivatives were prepared. For example, thiocholcine (compound IX) was prepared by reacting colchicine with sodium methyl sulfide (Velluz). Another colchicine derivative, 10-demethoxy-10-ethoxycolchicine (compound X) can be prepared by reacting colchicine with sodium ethoxide to generate 10-demethoxy-10-ethoxycolchicine. Colchicinamide (compound XI) can be formed by reaction of colchicine with ammonia in methanol (Lettre). Colchicinamide can be further reacted with ethyliodide to generate 10-demethoxy-10-ethylaminocolchicine (compound XII) (Bishop). Alternatively, 10-demethoxy-10-ethylaminocolchicine (compound XII) can be prepared directly from colchicine by reaction with ethylamine (Lettre).
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
[Compound]
Name
compound IX
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Five
Name
sodium methyl sulfide
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Six
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
Name
compound X
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Eight

Identifiers

REACTION_CXSMILES
[CH3:1][C:2]([NH:4][CH:5]1[C:21]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[C:18]([CH:20]=2)=[O:19])[C:13]2[C:8](=[CH:9][C:10]([O:28][CH3:29])=[C:11]([O:26][CH3:27])[C:12]=2[O:24][CH3:25])[CH2:7][CH2:6]1)=[O:3].CC([NH:33][C@@H]1C2C(=CC=C(OC)C(C=2)=O)C2C(OC)=C(OC)C(OC)=CC=2CC1)=O.CSC.[Na].CC(CC(C1C(O)=CC(O)=C(CC=C(C)C)C=1[O-])=O)C.[O-]CC.[Na+]>CO>[CH3:1][C:2]([NH:4][C@@H:5]1[C:21]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[C:18]([CH:20]=2)=[O:19])[C:13]2[C:12]([O:24][CH3:25])=[C:11]([O:26][CH3:27])[C:10]([O:28][CH3:29])=[CH:9][C:8]=2[CH2:7][CH2:6]1)=[O:3].[NH3:33] |f:2.3,5.6,^1:61|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CO
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[O-]CC.[Na+]
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(=O)NC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
Step Four
Name
compound IX
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Five
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(=O)N[C@H]1CCC=2C=C(C(=C(C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
Step Six
Name
sodium methyl sulfide
Quantity
0 (± 1) mol
Type
reactant
Smiles
CSC.[Na]
Step Seven
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(=O)N[C@H]1CCC=2C=C(C(=C(C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
Name
compound X
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(C)CC(=O)C1=C(C(=C(C=C1O)O)CC=C(C)C)[O-]
Step Eight
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(=O)N[C@H]1CCC=2C=C(C(=C(C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
were prepared

Outcomes

Product
Name
Type
product
Smiles
Name
Type
product
Smiles
CC(=O)N[C@H]1CCC=2C=C(C(=C(C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
Name
Type
product
Smiles
N

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US05426224

Procedure details

FIG. 6 illustrates how alternative colchine derivatives were prepared. For example, thiocholcine (compound IX) was prepared by reacting colchicine with sodium methyl sulfide (Velluz). Another colchicine derivative, 10-demethoxy-10-ethoxycolchicine (compound X) can be prepared by reacting colchicine with sodium ethoxide to generate 10-demethoxy-10-ethoxycolchicine. Colchicinamide (compound XI) can be formed by reaction of colchicine with ammonia in methanol (Lettre). Colchicinamide can be further reacted with ethyliodide to generate 10-demethoxy-10-ethylaminocolchicine (compound XII) (Bishop). Alternatively, 10-demethoxy-10-ethylaminocolchicine (compound XII) can be prepared directly from colchicine by reaction with ethylamine (Lettre).
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
[Compound]
Name
compound IX
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Five
Name
sodium methyl sulfide
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Six
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
Name
compound X
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Eight

Identifiers

REACTION_CXSMILES
[CH3:1][C:2]([NH:4][CH:5]1[C:21]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[C:18]([CH:20]=2)=[O:19])[C:13]2[C:8](=[CH:9][C:10]([O:28][CH3:29])=[C:11]([O:26][CH3:27])[C:12]=2[O:24][CH3:25])[CH2:7][CH2:6]1)=[O:3].CC([NH:33][C@@H]1C2C(=CC=C(OC)C(C=2)=O)C2C(OC)=C(OC)C(OC)=CC=2CC1)=O.CSC.[Na].CC(CC(C1C(O)=CC(O)=C(CC=C(C)C)C=1[O-])=O)C.[O-]CC.[Na+]>CO>[CH3:1][C:2]([NH:4][C@@H:5]1[C:21]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[C:18]([CH:20]=2)=[O:19])[C:13]2[C:12]([O:24][CH3:25])=[C:11]([O:26][CH3:27])[C:10]([O:28][CH3:29])=[CH:9][C:8]=2[CH2:7][CH2:6]1)=[O:3].[NH3:33] |f:2.3,5.6,^1:61|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CO
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[O-]CC.[Na+]
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(=O)NC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
Step Four
Name
compound IX
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Five
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(=O)N[C@H]1CCC=2C=C(C(=C(C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
Step Six
Name
sodium methyl sulfide
Quantity
0 (± 1) mol
Type
reactant
Smiles
CSC.[Na]
Step Seven
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(=O)N[C@H]1CCC=2C=C(C(=C(C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
Name
compound X
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(C)CC(=O)C1=C(C(=C(C=C1O)O)CC=C(C)C)[O-]
Step Eight
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(=O)N[C@H]1CCC=2C=C(C(=C(C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
were prepared

Outcomes

Product
Name
Type
product
Smiles
Name
Type
product
Smiles
CC(=O)N[C@H]1CCC=2C=C(C(=C(C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
Name
Type
product
Smiles
N

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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