2-Demethylthiocolchicine

Base Information

• Chemical Name: 2-Demethylthiocolchicine
• CAS No.: 87424-26-8
• Molecular Formula: C21H23NO5S
• Molecular Weight: 401.476
• DSSTox Substance ID: DTXSID40236341
• Nikkaji Number: J118.414H
• ChEMBL ID: CHEMBL277239
• Mol file: 87424-26-8.mol

Synonyms:2-demethylthiocolchicine

Chemical Property of 2-Demethylthiocolchicine

Chemical Property:

• Vapor Pressure: 2.34E-24mmHg at 25°C
• Melting Point: 218-220oC
• Boiling Point: 766.8°Cat760mmHg
• Flash Point: 417.6°C
• PSA: 110.16000
• Density: 1.33g/cm³
• LogP: 3.67280
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 401.12969401
• Heavy Atom Count: 28
• Complexity: 728

Purity/Quality:

99% ^*data from raw suppliers

2-DemethylThiocolchicine ^*data from reagent 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)SC)OC)O)OC
• Isomeric SMILES: CC(=O)N[C@H]1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)SC)OC)O)OC

Technology Process of 2-Demethylthiocolchicine

There total 3 articles about 2-Demethylthiocolchicine 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: 14.0%

thiocolchicine (2730-71-4) → N-((S)-2-hydroxy-1,3-dimethoxy-10-methylsulfanyl-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalen-7-yl)-acetamide (87424-26-8) + 2,3-didemethylthiocolchicine (51296-12-9) + 10-demethoxy-1-O,2-O-didemethyl-10-(methylthio)colchicine (51296-11-8)

Guidance literature:

With boron tribromide; In dichloromethane; 0 deg C, 1 h; room temperature, 6 h;

DOI:10.1080/00397919808006862

Reference yield:

2,3-didemethylthiocolchicine (51296-12-9) + diazomethyl-trimethyl-silane (18107-18-1) → N-((S)-2-hydroxy-1,3-dimethoxy-10-methylsulfanyl-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalen-7-yl)-acetamide (87424-26-8) + 3-O-demethylthiocolchicine (87424-25-7)

Guidance literature:

In methanol; hexane; chloroform; at 0 - 20 ℃; for 24h;

DOI:10.1016/j.bmcl.2004.07.098

Reference yield:

→ N-((S)-2-hydroxy-1,3-dimethoxy-10-methylsulfanyl-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalen-7-yl)-acetamide (87424-26-8)

Guidance literature:

With streptomyces griseus;

upstream raw materials:

thiocolchicine

2,3-didemethylthiocolchicine

diazomethyl-trimethyl-silane

Refernces

• 1、 Guan, Jian,Brossi, Arnold,Zhu, Xiao-Kang,Wang, Hui-Kang,Lee, Kuo-Hsiung. "Oxidation products of phenolic thiocolchicines: Ring a quinones and dienones". . p. 1585 - 1591. Retrieved 2007/10/03.
• 2、 VELLUZ,BELLET. "Selective demethylation of colchicine by microorganisms.". . p. 3453 - 3454. Retrieved 2007/10/17.