71155-05-0

Basic information

• Product Name: (+)-(1R 5S)-CIS-BICYCLO[3.2.0]HEPT-2-EN-
• Synonyms: (+)-(1R 5S)-CIS-BICYCLO[3.2.0]HEPT-2-EN-;(1R,5S)-(+)-6-Oxobicyclo[3.2.0]hept-2-ene;(1R,5S)-(+)-Bicyclo[3.2.0]hept-2-en-6-one;Bicyclo[3.2.0]hept-2-en-6-one,(1R,5S)-;(+)-(1R 5S)-CIS-BICYCLO[3.2.0]HEPT-2-EN-6-One (1R,5S)-(+)-Bicyclo[3.2.0]hept-2-en-6-one
• CAS NO: 71155-05-0
• Molecular Formula: C₇H₈O
• Molecular Weight: 108.14
• Product Categories: Chiral Building Blocks;Ketones;Organic Building Blocks
• Mol File: 71155-05-0.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 186.6±9.0 °C(Predicted)
• Appearance: /
• Density: 1.138±0.06 g/cm3(Predicted)
• Refractive Index: n20/D 1.483
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (+)-(1R 5S)-CIS-BICYCLO[3.2.0]HEPT-2-EN-(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(1R 5S)-CIS-BICYCLO[3.2.0]HEPT-2-EN-(71155-05-0)
• EPA Substance Registry System: (+)-(1R 5S)-CIS-BICYCLO[3.2.0]HEPT-2-EN-(71155-05-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• WGK Germany: 3
• F: 8-10-23
• Hazardous Substances Data: 71155-05-0(Hazardous Substances Data)

Usage

General Description

(+)-(1R, 5S)-CIS-BICYCLO[3.2.0]HEPT-2-EN- is a chemical compound with a bicyclic structure. It is a stereoisomer of the bicycloheptene family, with the specific stereochemistry of the substituents at positions 1 and 5 being R and S, respectively. (+)-(1R 5S)-CIS-BICYCLO[3.2.0]HEPT-2-EN- is used in organic synthesis and can be utilized as a chiral building block for the preparation of various pharmaceuticals, natural products, and other biologically active molecules. Its unique structure and stereochemistry make it an important intermediate in the production of complex organic compounds. Additionally, it has potential applications in the development of new drugs and agrochemicals.

Upstream product

• 925211-06-9 bicyclo(3.2.0)hept-2-en-6-one 
• 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

• 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 
• 103618-27-5 (+)-(1S,5R)-3-oxabicyclo<3.3.0>oct-6-en-2-one 
• 59829-44-6 (1S,2S,4R,6S)-8-oxo-3,7-dioxatricyclo<4.3.0.0^2,4>nonane 
• 80735-00-8 (1S,2R,4S,6S)-8-oxo-3,7-dioxatricyclo<4.3.0.0^2,4>nonane 
• 92207-95-9 C₁₅H₁₉NO₂S 
• 92207-95-9 C₁₅H₁₉NO₂S 
• 128946-78-1 3-oxabicyclo[3.3.0]oct-6-en-2-one 
• 77670-72-5 3-chloro-2-(2-nitrophenylthio)bicyclo<3.2.0>heptan-6-one 
• 73057-70-2 cis-bicyclo<3.2.0>hept-2-en-6-one ethylene acetal 
• 89849-79-6 Toluene-4-sulfonic acid (1S,5R)-7-oxo-bicyclo[3.2.0]hept-3-en-(6Z)-ylidenemethyl ester 
• 77670-70-3 (1S,2R,3R,5S)-3-Chloro-2-phenylsulfanyl-bicyclo[3.2.0]heptan-6-one 
• 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 

Relevant articles and documents

Identification of novel mammalian squalene synthase inhibitors using a three-dimensional pharmacophore

Squalene synthase (E.C. 2.5.1.21) catalyses the reductive dimerisation of farnesyl diphosphate in a [1-4] head to head fashion to form squalene, and is the first committed step in cholesterol biosynthesis. Specific inhibitors of squalene synthase would inhibit cholesterol formation and allow production of other important compounds derived from the cholesterol biosynthetic pathway, namely the ubiquinones (co-enzyme Q10), dolichol, and would also allow the isoprenylation process of ras by farnesyl-protein transferase. The construction of a hypothetical squalene synthase three-dimensional pharmacophore is presented. It serves as a template for the identification of several new potential classes of inhibitors. The synthesis, anti-microbial and mammalian pig liver squalene synthase activities of analogues based on the bicyclo[3.2.0]heptane and bicyclo[3.3.0]octane ring systems are reported. Analogues of the latter system are pro-drug type inhibitors and exhibit promising biological activity.

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.