1-Demethylcolchicine

Base Information

• Chemical Name: 1-Demethylcolchicine
• CAS No.: 3464-68-4
• Molecular Formula: C21H23NO6
• Molecular Weight: 385.417
• NSC Number: 317026
• ChEMBL ID: CHEMBL89092
• Mol file: 3464-68-4.mol

Synonyms:1-Demethylcolchicine;3464-68-4;N-[(7S)-1-hydroxy-2,3,10-trimethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide;CHEMBL89092;SCHEMBL15151764;NSC317026;NSC-317026

Chemical Property of 1-Demethylcolchicine

Chemical Property:

• Vapor Pressure: 6.65E-23mmHg at 25°C
• Boiling Point: 744.2°Cat760mmHg
• Flash Point: 403.9°C
• Density: 1.31g/cm³
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 385.15253745
• Heavy Atom Count: 28
• Complexity: 724

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)O)OC)OC
• Isomeric SMILES: CC(=O)N[C@H]1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)O)OC)OC

Technology Process of 1-Demethylcolchicine

There total 3 articles about 1-Demethylcolchicine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

N-[(7S)-2,3,10-trimethoxy-1-((methyl)carbonyloxy)-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide (3306-60-3) → N-[(7S)-1-hydroxy-2,3,10-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide (3464-68-4)

Guidance literature:

With sodium hydroxide; water; In methanol; for 5h; Ambient temperature;

Reference yield:

colchicine (64-86-8,54192-66-4) → N-[(7S)-1-hydroxy-2,3,10-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide (3464-68-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 36 percent / SnCl₄ / CH₂Cl₂ / 30 h / Ambient temperature

2: NaOH, H₂O / methanol / 5 h / Ambient temperature

With sodium hydroxide; water; tin(IV) chloride; In methanol; dichloromethane;

Reference yield:

→ N-[(7S)-1-hydroxy-2,3,10-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide (3464-68-4)

Guidance literature:

upstream raw materials:

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

colchicine

Downstream raw materials:

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

Refernces

• 1、 -. "NOVEL COLCHICINE DERIVATIVES, METHODS AND USES THEREOF". Page/Page column 83. . Retrieved 2011/04/14.
• 2、 McDonald, Edward,Ramage, Robert,Woodhouse, Robert N.,Underbill, Edward W.,Wetter, Leslie R.,Battersby, Alan R.. "Biosynthesis. Part 27.1,2 Colchicine: Studies of the phenolic oxidative coupling and ring-expansion processes based on incorporation of multiply labelled 1-phenethylisoquinolines". . p. 2979 - 2987. Retrieved 2007/10/03.