92998-64-6

Basic information

• Product Name: 7,7-Dichlorobicyclo[3.2.0]hept-2-en-6-ol
• Synonyms: 7,7-Dichlorobicyclo[3.2.0]hept-2-en-6-ol
• CAS NO: 92998-64-6
• Molecular Formula: C₇H₈Cl₂O
• Molecular Weight: 0
• Mol File: 92998-64-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7,7-Dichlorobicyclo[3.2.0]hept-2-en-6-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 7,7-Dichlorobicyclo[3.2.0]hept-2-en-6-ol(92998-64-6)
• EPA Substance Registry System: 7,7-Dichlorobicyclo[3.2.0]hept-2-en-6-ol(92998-64-6)

Safety Data

• Hazardous Substances Data: 92998-64-6(Hazardous Substances Data)

Upstream product

• 19296-95-8 (1R,5S,6R)-7,7-Dichloro-bicyclo[3.2.0]hept-2-en-6-ol 
• 5307-99-3 (+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one 
• 5307-99-3 7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one 
• 130721-18-5 (1RS,5SR,6RS)-7,7-dichlorobicyclo<3.2.0>hept-2-en-6-yl butyrate 
• 542-92-7 cyclopenta-1,3-diene 

Downstream Products

• 19296-95-8 (1S,5R,6S)-7,7-Dichloro-bicyclo[3.2.0]hept-2-en-6-ol 
• 100-42-5 styrene 
• 92901-43-4 3-(dichloromethyl)-4-vinylcyclopentene 
• 75415-75-7 2-chlorobicyclo<3.2.1>octa-2,6-diene 

Relevant articles and documents

A practical route to both enantiomers of bicyclo[3.3.0]oct-2-en-7-one and their use for the synthesis of key trisubstituted cyclopentanes

We describe new methodology for the synthesis of both enantiomers of 7,7-dichlorobicyclo[3.2.0]hep-2-en-6-one and conversion of these compounds into stereochemically defined bicyclo[3.3.0]oct-2-en-7-ones and thence trisubstituted cyclopentanes. These are key intermediates for the synthesis of prostanoids, brefeldin and other cyclopentane-containing natural products.

BIOCATALYTIC PREPARATION OF BICYCLOHEPTANE DERIVATIVES

Bicyclohept-2-en-6-ols, central building blocks for the synthesis of chiral cyclobutane and -pentane systems, were prepared with up to >99percent e.e. by lipase catalysed resolution of their acetates, butyrates, or isobutyrates.Substituents at C-7 vicinal to the reaction site reduced both enantioselectivity and reaction rate, whereas variation of the acid moiety showed a smaller influence.Among the lipases tested, those from Pseudomonas sp. were shown to be superior to those from Candida cylindracea, Mucor sp. and porcine pancreas.

Acid-catalyzed rearrangement of cyclobutanols. Syntheses of chrysenes, cyclopentenophenanthrenes, and diarylmethanes

Acid-catalyzed reactions of 8-aryl or 8,8-diarylbicyclooct-2-en-7-ols lead to tetrahydrophenanthrene derivatives.For example 8-(1-naphthyl)-bicyclooct-2-en-7-ols give substituted chrysenes in methanesulphonic acid.In the case of the homologous 7-aryl or 7,7-diarylbicyclohept-2-en-6-ols a novel transformation of diarylmethanes is observed.A mechanism is proposed which accounts for the product distribution observed in these rearrangements.