2,3-bis(1H-indol-3-yl)-N-benzylmaleimide

Base Information

• Chemical Name: 2,3-bis(1H-indol-3-yl)-N-benzylmaleimide
• CAS No.: 91026-01-6
• Molecular Formula: C27H19N3O2
• Molecular Weight: 417.467
• ChEMBL ID: CHEMBL298346
• DSSTox Substance ID: DTXSID00463590
• Nikkaji Number: J2.732.833D
• Wikidata: Q82288545
• Mol file: 91026-01-6.mol

Synonyms:CHEMBL298346;2,3-bis(1H-indol-3-yl)-N-benzylmaleimide;91026-01-6;1-benzyl-3,4-bis(1H-indol-3-yl)pyrrole-2,5-dione;SCHEMBL7193605;DTXSID00463590;KCTMKNTUYXUDDV-UHFFFAOYSA-N;BDBM50199960;1-Benzyl-3,4-bis-(1H-indol-3-yl)-pyrrole-2,5-dione;1-benzyl-3,4-di(1H-indol-3-yl)-1H-pyrrole-2,5-dione

Chemical Property of 2,3-bis(1H-indol-3-yl)-N-benzylmaleimide

Chemical Property:

• XLogP3: 4.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 417.147726857
• Heavy Atom Count: 32
• Complexity: 732

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CN2C(=O)C(=C(C2=O)C3=CNC4=CC=CC=C43)C5=CNC6=CC=CC=C65

Technology Process of 2,3-bis(1H-indol-3-yl)-N-benzylmaleimide

There total 11 articles about 2,3-bis(1H-indol-3-yl)-N-benzylmaleimide 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: 94.0%

N-Benzyl-3,4-di(indol-3-yl)succinimide (115684-55-4) → 2,3-bis(1H-indol-3-yl)-N-benzylmaleimide (91026-01-6)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; Ambient temperature;

DOI:10.1016/S0040-4039(00)96533-X

Reference yield: 86.6%

2,3-bis(1H-indol-3-yl)maleic anhydride (115684-57-6) + benzylamine (100-46-9) → 2,3-bis(1H-indol-3-yl)-N-benzylmaleimide (91026-01-6)

Guidance literature:

In water; N,N-dimethyl-formamide;

Reference yield: 70.0%

indole (120-72-9) + N-benzyl-2,3-dibromo-maleimide (91026-00-5) → 2,3-bis(1H-indol-3-yl)-N-benzylmaleimide (91026-01-6)

Guidance literature:

indole; With ethylmagnesium chloride; In tetrahydrofuran; toluene; at 45 ℃; for 0.75h; Inert atmosphere;

N-benzyl-2,3-dibromo-maleimide; In tetrahydrofuran; toluene; for 12h; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2009.04.090

upstream raw materials:

indole

N-benzyl-2,3-dibromo-maleimide

N-Benzyl-3,4-di(indol-3-yl)succinimide

1-benzyl-3,4-dichloro-pyrrole-2,5-dione

Downstream raw materials:

6-benzyl-12,13-dihydro-6H-indolo<2,3-a>pyrrolo<3,4-c>carbazole-5,7-dione

{3-[1-Benzyl-4-(1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-indol-1-yl}-acetic acid ethyl ester

(9R)-6,7,10,11-tetrahydro-19-(phenylmethyl)-9-cyano-9H,18H-5,21:12,17-dimethenodibenzo[e,k]pyrrolo[3,4-h][1,4,13]oxadiazacyclohexadecine-18,20(19H)-dione

1-benzyl-3-(1-cyclopent-3-enyl-1H-indol-3-yl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione

Refernces

• 1、 Lin, Zhenghuan,Chen, Hung Cheng,Sun, Shih-Sheng,Hsu, Chao-Ping,Chow, Tahsin J.. "Bifunctional maleimide dyes as selective anion sensors". experimental part. p. 5216 - 5221. Retrieved 2009/11/30.
• 2、 Bartlett, Stephen,Nelson, Adam. "Evaluation of alternative approaches for the synthesis of macrocyclic bisindolylmaleimides". . p. 2874 - 2883. Retrieved 2007/10/03.