13173-09-6

Basic information

• Product Name: (+/-)-cis-Bicyclo[3.2.0]hept-2-en-6-one
• Synonyms: BICYCLO[3.2.0]HEPT-2-EN-6-ONE;Bicyclo(3.2.0)hept-2-en-6-one,96%;Bicyclohepten;(+/-)-cis-Bicyclo[3.2.0]hept-2-en-6-one;Bicyclo3.2.0ühept-2-en-6-one, 97%;Bicyclo[3.2.0]hept-2-en-6-one bisulphite adduct;(±)-cis-Bicyclo[3.2.0]hept-2-en-6-one;(+/-)-cis-Bicyclo[3.2.0]hept-2-en-6-one >=98.0%
• CAS NO: 13173-09-6
• Molecular Formula: C₇H₈O
• Molecular Weight: 108.14
• Product Categories: C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 13173-09-6.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 158-160 °C(lit.)
• Flash Point: 66.3°C
• Appearance: /
• Density: 1.025 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.658mmHg at 25°C
• Refractive Index: n20/D 1.4820(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive: Air Sensitive
• CAS DataBase Reference: (+/-)-cis-Bicyclo[3.2.0]hept-2-en-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-cis-Bicyclo[3.2.0]hept-2-en-6-one(13173-09-6)
• EPA Substance Registry System: (+/-)-cis-Bicyclo[3.2.0]hept-2-en-6-one(13173-09-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• RIDADR: UN1224
• WGK Germany: 3
• F: 10-23
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 13173-09-6(Hazardous Substances Data)

Usage

Uses

Bicyclo[3.2.0]hept-2-en-6-one is widely utilized to study enantioselective Baeyer-Villiger oxidation of (±)-cis-bicyclo(3.2.0)hept-2-en-6-one. It is used in the synthesis of a series of chalcone derivatives by reacting with arylaldehydes. It is also used to analyze the extremophile enzymes (monooxygenase and hydrolases) in microorganisms which are isolated from a deep-water petroleum reservoir and at high temperatures using fluorogenic assays and multibioreactions.

General Description

(±)-cis-bicyclo(3.2.0)hept-2-en-6-one undergoes preparative scale Baeyer–Villiger biooxidation at high concentration using recombinant Escherichia coli biocatalyst and adsorbent resin (in situ substrate feeding and product removal).

InChI:InChI=1/C7H8O/c8-7-4-5-2-1-3-6(5)7/h1-2,5-6H,3-4H2/t5-,6-/m1/s1

Upstream product

• 5307-99-3 7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one 
• 79-36-7 dichloroacethyl chloride 
• 542-92-7 cyclopenta-1,3-diene 
• 13259-28-4 (rac)-6-endo-bicyclo<3.2.0>hept-2-en-6-ol 
• 13259-28-4 (+/-)-exo-bicyclo<3.2.0>hept-2-en-6-ol 
• 4591-28-0 dichloroketene 
• 20836-85-5 7endo-chlorobicyclo<3.2.0>hept-2-en-6-one 

Downstream Products

• 92207-95-9 C₁₅H₁₉NO₂S 
• 92207-95-9 C₁₅H₁₉NO₂S 
• 34638-25-0 (1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 128946-78-1 3-oxabicyclo[3.3.0]oct-6-en-2-one 
• 103618-27-5 (+)-(1S,5R)-3-oxabicyclo<3.3.0>oct-6-en-2-one 
• 73057-70-2 cis-bicyclo<3.2.0>hept-2-en-6-one ethylene acetal 
• 56011-38-2 3-endo-benzyloxy-2-exo-bromobicyclo<3.2.0>heptan-6-one 
• 26054-46-6 cis-(±)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 1357495-82-9 benzyl 2-(6-oxo-2,4,5,6-tetrahydrocyclopenta[c]pyrrol-4-yl)-acetate 
• 68372-66-7 1β,5β,7α,-7-hydroxy-2-oxabicyclo<3.3.0>octan-3-one 
• 158604-58-1 benzyl 2-(4-oxocyclopent-2-en-1-yl)acetate 
• 34638-25-0 2-oxabicyclo[3.3.0]oct-6-en-3-one 

Relevant articles and documents

REDUCTION OF 7-CHLOROBICYCLOHEPT-2-EN-6-ONES CATALYSED BY 3α,20β-HYDROXYSTEROID DEHYDROGENASE

7,7-Dichlorobicyclohept-2-en-6-one and 7endo-chlorobicyclohept-2-en-6-one are reduced regio-specifically and with high substrate enantioselectivity using a 3α,20β-hydroxysteroid alcohol dehydrogenase.

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Thermal rearrangement of 7-methylbicyclo[3.2.0]hept-2-ene: An experimental probe of the extent of orbital symmetry control in the [1,3] sigmatropic rearrangement

The gas-phase thermal rearrangement of exo-7-methylbicyclo[3.2.0]hept-2-ene yields almost exclusively 5-methylnorbornene products. Inversion (i) of configuration dominates this [1,3] sigmatropic shift although some retention (r) is also observed. Because the [1,3] migration can only occur suprafacially (s) in this geometrically constrained system, the si/sr ratio of 7 observed for the migration of C7 in exo-7-methylbicyclo[3.2.0]hept-2-ene indicates that the orbital symmetry rules are somewhat permissive for the [1,3] sigmatropic migration of carbon.

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.