17202-32-3

Basic information

• Product Name: 2,3-Dibromo-1-cyclohexene
• Synonyms: 1,6-Dibromocyclohexene;2,3-Dibromo-1-cyclohexene
• CAS NO: 17202-32-3
• Molecular Formula: C₆H₈Br₂
• Molecular Weight: 239.94
• Mol File: 17202-32-3.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3-Dibromo-1-cyclohexene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dibromo-1-cyclohexene(17202-32-3)
• EPA Substance Registry System: 2,3-Dibromo-1-cyclohexene(17202-32-3)

Safety Data

• Hazardous Substances Data: 17202-32-3(Hazardous Substances Data)

Upstream product

• 2568-36-7 6,6-dibromobicylo[3.1.0]hexane 
• 142-29-0 cyclopentene 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 144773-93-3 1,5-dibromocyclopentene 
• 75-25-2 Bromoform 
• 89641-49-6 1,2,3-Tribrom-cyclohexan 

Downstream Products

• 118451-61-9 (2-bromo-cyclohex-2-enyl)-trimethyl-silane 
• 122135-92-6 (3Z)-4,5,6,7-tetrahydro-3-benzylideneisobenzofuran-1(3H)-one 
• 152510-75-3 (2-Bromo-cyclohex-2-enyl)-dimethyl-phenyl-silane 
• 3727-47-7 1-bromocyclohexa-1,3-diene 
• 3727-48-8 2-bromocyclohexa-1,3-diene 
• 16253-85-3 1-Bromo-6-ethoxy-cyclohexene 

Relevant articles and documents

Divergent Synthesis of Bioactive Dithiodiketopiperazine Natural Products Based on a Double C(sp3)?H Activation Strategy

This article provides a detailed report of our efforts to synthesize the dithiodiketopiperazine (DTP) natural products (?)-epicoccin G and (?)-rostratin A using a double C(sp3)?H activation strategy. The strategy's viability was first established on a model system lacking the C8/C8’ alcohols. Then, an efficient stereoselective route including an organocatalytic epoxidation was secured to access a key bis-triflate substrate. This bis-triflate served as the functional handles for the key transformation of the synthesis: a double C(sp3)?H activation. The successful double activation opened access to a common intermediate for both natural products in high overall yield and on a multigram scale. After several unsuccessful attempts, this intermediate was efficiently converted to (?)-epicoccin G and to the more challenging (?)-rostratin A via suitable oxidation/reduction and protecting group sequences, and via a final sulfuration that occurred in good yield and high diastereoselectivity. These efforts culminated in the synthesis of (?)-epicoccin G and (?)-rostratin A in high overall yields (19.6 % over 14 steps and 12.7 % over 17 steps, respectively), with the latter being obtained on a 500 mg scale. Toxicity assessments of these natural products and several analogues (including the newly synthesized epicoccin K) in the leukemia cell line K562 confirmed the importance of the disulfide bridge for activity and identified dianhydrorostratin A as a 20x more potent analogue.

Synthesis of hexahydroindoles by intramolecular C sp 3-H alkenylation: Application to the synthesis of the core of aeruginosins

Give me five: Pd-catalyzed intramolecular C sp 3-H arylations have been successfully extended to alkenylations. This method shows remarkable selectivity and gives synthetically useful hexahydroindoles, as illustrated with the synthesis of the octahydroind

Catalytic formal homo-Nazarov cyclization

The first catalytic method for the cyclization of vinyl-cyclopropyl ketones (formal homo-Nazarov reaction) is reported. Starting from activated cyclopropanes, heterocyclic, and carbocyclic compounds were obtained under mild conditions using Bronsted acid catalysts. Preliminary investigation of the reaction mechanism indicated a stepwise process.