Asperlicin C

Base Information

• Chemical Name: Asperlicin C
• CAS No.: 93413-06-0
• Molecular Formula: C₂₅H₁₈N₄O₂
• Molecular Weight: 406.444
• UNII: 6LSO8H0C9H
• DSSTox Substance ID: DTXSID00918454
• Nikkaji Number: J969.864G
• Wikidata: Q27162892
• Metabolomics Workbench ID: 98498
• Mol file: 93413-06-0.mol

Synonyms:asperlicin C

Chemical Property of Asperlicin C

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 79.78000
• Density: 1.43g/cm³
• LogP: 4.22300
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 406.14297583
• Heavy Atom Count: 31
• Complexity: 767

Purity/Quality:

ASPERLICIN C 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CC3C4=NC5=CC=CC=C5C(=O)N4C6=CC=CC=C6C(=O)N3
• Isomeric SMILES: C1=CC=C2C(=C1)C(=CN2)C[C@H]3C4=NC5=CC=CC=C5C(=O)N4C6=CC=CC=C6C(=O)N3

Technology Process of Asperlicin C

There total 12 articles about Asperlicin C 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: 80.0%

(S)-1-(2-Azido-benzoyl)-3-(1H-indol-3-ylmethyl)-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione → (7S)-6,7-dihydro-7-(1H-indol-3-ylmethyl)quinazolino[3,2-a][1,4]benzodiazepine-5,13-dione (93413-06-0)

Guidance literature:

With tributylphosphine; In benzene; at 60 ℃;

DOI:10.1021/ja9809408

Reference yield: 79.0%

(S)-3-indol-1-(2-nitrobenzoyl)-3,4-dihydro-1H-benzo[1,4]diazepine-2,5-dione → (7S)-6,7-dihydro-7-(1H-indol-3-ylmethyl)quinazolino[3,2-a][1,4]benzodiazepine-5,13-dione (93413-06-0)

Guidance literature:

With titanium tetrachloride; zinc; In tetrahydrofuran; at -78 - 23 ℃; for 54h; Temperature;

DOI:10.1016/j.tetlet.2015.01.084

Reference yield: 68.0%

L-Trp-Abz-Abz-OMe (1129527-31-6) → (7S)-6,7-dihydro-7-(1H-indol-3-ylmethyl)quinazolino[3,2-a][1,4]benzodiazepine-5,13-dione (93413-06-0)

Guidance literature:

With scandium tris(trifluoromethanesulfonate); In N,N-dimethyl-formamide; at 140 ℃; for 0.25h; Microwave irradiation;

DOI:10.1039/b910545j

upstream raw materials:

o-azidobenzoyl chloride

(S)-3-[(1H-indol-3-yl)methyl]-3,4-dihydro-1H-benzo[1,4]diazepine-2,5-dione

L-Trp-Abz-Abz-OMe

Boc-Trp-OH

Downstream raw materials:

asperlicin E

Refernces

• 1、 Huang, Pei-Qiang,Wang, Yu,Luo, Shi-Peng,Geng, Hui,Ruan, Yuan-Ping,Wang, Ai-E. "Procedure - Economical enantioselective total syntheses of asperlicins C and e". . p. 1255 - 1258. Retrieved 2015/03/04.
• 2、 Tseng, Ming-Chung,Yang, Huei-Yun,Chu, Yen-Ho. "Total synthesis of asperlicin C, circumdatin F, demethylbenzomalvin A, demethoxycircumdatin H, sclerotigenin, and other fused quinazolinones". experimental part. p. 419 - 427. Retrieved 2010/02/16.