4-bromo-5,6-dihydrocyclopenta[c]pyrrole-1,3(2H,4H)-dione

Base Information

• Chemical Name: 4-bromo-5,6-dihydrocyclopenta[c]pyrrole-1,3(2H,4H)-dione
• CAS No.: 80016-36-0
• Molecular Formula: C7H6 Br N O2
• Molecular Weight: 216.032
• Mol file: 80016-36-0.mol

Synonyms:NSC293560

Chemical Property of 4-bromo-5,6-dihydrocyclopenta[c]pyrrole-1,3(2H,4H)-dione

Chemical Property:

• Vapor Pressure: 1.91E-05mmHg at 25°C
• Boiling Point: 362.6°Cat760mmHg
• Flash Point: 173.1°C
• Density: 1.85g/cm³

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-bromo-5,6-dihydrocyclopenta[c]pyrrole-1,3(2H,4H)-dione

There total 7 articles about 4-bromo-5,6-dihydrocyclopenta[c]pyrrole-1,3(2H,4H)-dione 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: 78.0%

2,4-dioxo-3-azabicyclo<3.3.0>oct-Δ1,5-ene (62291-38-7) → 3-aza-6-bromo-bicyclo<3.3.0>-1-octene-2,4-dione (80016-36-0)

Guidance literature:

With N-Bromosuccinimide; In chloroform; for 0.333333h; Inert atmosphere; Irradiation;

DOI:10.1016/j.tetlet.2015.01.143

Reference yield:

2-trifluoromethanesulfonyloxy-cyclopent-1-enecarboxylic acid ethyl ester (122539-74-6) → 3-aza-6-bromo-bicyclo<3.3.0>-1-octene-2,4-dione (80016-36-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: palladium diacetate; lithium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 20 °C / Molecular sieve

2.1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 1.17 h / 0 - 20 °C

2.2: 0 °C

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 °C

4.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / benzene / 1 h / 80 °C

With N-Bromosuccinimide; thionyl chloride; 2,2'-azobis(isobutyronitrile); palladium diacetate; sodium hydride; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; lithium chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; mineral oil; benzene;

DOI:10.1002/ejoc.202000767

Reference yield:

2-ethoxycarbonyl-1-cyclopentanone (611-10-9) → 3-aza-6-bromo-bicyclo<3.3.0>-1-octene-2,4-dione (80016-36-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / 0 - 20 °C

2.1: palladium diacetate; lithium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 20 °C / Molecular sieve

3.1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 1.17 h / 0 - 20 °C

3.2: 0 °C

4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 °C

5.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / benzene / 1 h / 80 °C

With N-Bromosuccinimide; thionyl chloride; 2,2'-azobis(isobutyronitrile); palladium diacetate; sodium hydride; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; lithium chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; mineral oil; benzene; 1.1: |Dieckmann Condensation;

DOI:10.1002/ejoc.202000767

upstream raw materials:

2,4-dioxo-3-azabicyclo<3.3.0>oct-Δ^1,5-ene

cyclopent-1-ene-1,2-dicarboxylic acid

2-trifluoromethanesulfonyloxy-cyclopent-1-enecarboxylic acid ethyl ester

2-ethoxycarbonyl-1-cyclopentanone

Downstream raw materials:

(R/S)-4-hydroxy-5,6-dihydrocyclopenta[c]pyrrole-1,3(2H,4H)-dione

(S)-4-hydroxy-5,6-dihydrocyclopenta[c]pyrrole-1,3(2H,4H)-dione

Refernces

• 1、 Philkhana, Satish Chandra,Verma, Abhishek Kumar,Jachak, Gorakhnath R.,Hazra, Bibhabasu,Basu, Anirban,Reddy, D. Srinivasa. "Identification of new anti-inflammatory agents based on nitrosporeusine natural products of marine origin". . p. 89 - 109. Retrieved 2017/04/26.
• 2、 Singh,Weinreb. "An efficient total synthesis of maleimycin". . p. 2379 - 2380. Retrieved 2007/10/11.