N-[(10S)-3,4,5,14-tetramethoxy-13-oxo-10-tetracyclo[9.5.0.02,7.012,16]hexadeca-1(11),2,4,6,14-pentaenyl]acetamide

Base Information

• Chemical Name: N-[(10S)-3,4,5,14-tetramethoxy-13-oxo-10-tetracyclo[9.5.0.02,7.012,16]hexadeca-1(11),2,4,6,14-pentaenyl]acetamide
• CAS No.: 6901-13-9
• Molecular Formula: C22H25NO6
• Molecular Weight: 399.444
• European Community (EC) Number: 230-008-1
• Mol file: 6901-13-9.mol

Synonyms:6901-13-9;SCHEMBL2007125;Acetamide, N-[(7S,7bR,10aS)-5,6,7,7b,8,10a-hexahydro-1,2,3,9-tetramethoxy-8-oxobenzo[a]cyclopenta[3,4]cyclobuta[1,2-c]cyclohepten-7-yl]-

Chemical Property of N-[(10S)-3,4,5,14-tetramethoxy-13-oxo-10-tetracyclo[9.5.0.02,7.012,16]hexadeca-1(11),2,4,6,14-pentaenyl]acetamide

Chemical Property:

• Melting Point: 177-180°C
• Boiling Point: 623.227 °C at 760 mmHg
• Flash Point: 330.716 °C
• PSA: 83.09000
• Density: 1.3 g/cm³
• LogP: 2.66680
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Sparingly)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 399.16818752
• Heavy Atom Count: 29
• Complexity: 758

Purity/Quality:

99%, ^*data from raw suppliers

β-Lumi(-)-Colchicine ^*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=C1C4C3C=C(C4=O)OC)OC)OC)OC
• Isomeric SMILES: CC(=O)N[C@H]1CCC2=CC(=C(C(=C2C3=C1C4C3C=C(C4=O)OC)OC)OC)OC
• Description: This alkaloid has been isolated from a number of plants including Colchicum kesselringii, C. luteum Baker, Merendera jolanta E. Czerniak, M. raddeana Rgl.and M. robusta Bge. It forms colourless crystals from CHC13-Et20. It is possible that this base may be an artifact formed during the isolation process.
• Uses: An analog of Colchicine (C640000), β-lumicolchicine, does not bind tubulin or disrupt microtubules. A GABAA receptor chloride channel. An analog of Colchicine (C640000), β-lumicolchicine, does not bind tubulin or disrupt microtubules.

Technology Process of N-[(10S)-3,4,5,14-tetramethoxy-13-oxo-10-tetracyclo[9.5.0.02,7.012,16]hexadeca-1(11),2,4,6,14-pentaenyl]acetamide

There total 9 articles about N-[(10S)-3,4,5,14-tetramethoxy-13-oxo-10-tetracyclo[9.5.0.02,7.012,16]hexadeca-1(11),2,4,6,14-pentaenyl]acetamide 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: 68.0%

colchicine (64-86-8,54192-66-4) → lumicolchicine (6901-13-9)

Guidance literature:

In acetone; acetonitrile; for 0.416667h; Irradiation;

DOI:10.1021/acs.orglett.7b02224

Reference yield:

C21H23NO6 → lumicolchicine (6901-13-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: 24.5 h / 0 - 20 °C / Inert atmosphere

2.1: palladium dichloride; copper diacetate; oxygen / water; acetonitrile / 16 h / 120 °C

3.1: trimethylsilyl trifluoromethanesulfonate; N,N-dimethyl-ethanamine / dichloromethane / 12 h / 20 °C / Inert atmosphere

4.1: acetonitrile; acetone / 0.42 h / Irradiation

With N,N-dimethyl-ethanamine; trimethylsilyl trifluoromethanesulfonate; oxygen; copper diacetate; diisobutylaluminium hydride; palladium dichloride; In tetrahydrofuran; dichloromethane; water; acetone; acetonitrile;

DOI:10.1021/acs.orglett.7b02224

Reference yield:

C22H27NO6 → lumicolchicine (6901-13-9)

Guidance literature:

Multi-step reaction with 3 steps

1: palladium dichloride; copper diacetate; oxygen / water; acetonitrile / 16 h / 120 °C

2: trimethylsilyl trifluoromethanesulfonate; N,N-dimethyl-ethanamine / dichloromethane / 12 h / 20 °C / Inert atmosphere

3: acetonitrile; acetone / 0.42 h / Irradiation

With N,N-dimethyl-ethanamine; trimethylsilyl trifluoromethanesulfonate; oxygen; copper diacetate; palladium dichloride; In dichloromethane; water; acetone; acetonitrile;

DOI:10.1021/acs.orglett.7b02224

upstream raw materials:

methanol

colchicine

water

diazomethane

Refernces

• 1、 Liu, Xin,Hu, Ya-Jian,Chen, Bo,Min, Long,Peng, Xiao-Shui,Zhao, Jing,Li, Shaoping,Wong, Henry N. C.,Li, Chuang-Chuang. "Asymmetric Total Syntheses of Colchicine, β-Lumicolchicine, and Allocolchicinoid N-Acetylcolchinol-O-methyl Ether (NCME)". . p. 4612 - 4615. Retrieved 2017/09/12.
• 2、 Bussotti, Laura,Cacelli, Ivo,D'Auria, Maurizio,Foggi, Paolo,Lesma, Giordano,Silvani, Alessandra,Villani, Vincenzo. "Photochemical Isomerization of Colchicine and Thiocolchicine". . p. 9079 - 9085. Retrieved 2007/10/03.