72229-06-2

Basic information

• Product Name: Bicyclo[3.1.0]hexane-6-carboxylic Acid Ethyl Ester (endo/exo Mixture)
• Synonyms: Bicyclo[3.1.0]hexane-6-carboxylic Acid Ethyl Ester (endo/exo Mixture);Bicyclo[3.1.0]hexane-6-carboxylic Acid Ethyl Ester \n(endo/exo Mixture)
• CAS NO: 72229-06-2
• Molecular Formula: C₉H₁₄O₂
• Molecular Weight: 154.20626
• Product Categories: Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 72229-06-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Bicyclo[3.1.0]hexane-6-carboxylic Acid Ethyl Ester (endo/exo Mixture)(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[3.1.0]hexane-6-carboxylic Acid Ethyl Ester (endo/exo Mixture)(72229-06-2)
• EPA Substance Registry System: Bicyclo[3.1.0]hexane-6-carboxylic Acid Ethyl Ester (endo/exo Mixture)(72229-06-2)

Safety Data

• Hazardous Substances Data: 72229-06-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Bicyclo[3.1.0]hexane-6-carboxylic Acid Ethyl Ester (endo/exo Mixture) is used as an intermediate in the synthesis of various pharmaceutical goods. Its unique bicyclic structure and functional groups make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Antibiotic Synthesis:
Bicyclo[3.1.0]hexane-6-carboxylic Acid Ethyl Ester (endo/exo Mixture) is used in the preparation of BRL 56173, a bicyclic acrylic penicillin that is highly stable to β-lactamases. This antibiotic is effective against a wide range of gram-positive and some gram-negative bacteria, making it a valuable treatment option for various infections caused by antibiotic-resistant strains.

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 142-29-0 cyclopentene 

Downstream Products

• 16650-37-6 bicyclo[3.1.0]hexane-6-carboxylic acid 
• 4971-24-8 1α,5α,6α-bicyclo[3.1.0]hexane-6-carboxylic acid 
• 3313-85-7 6-(hydroxymethyl)-exobicyclo[3.1.0]hexane 
• 30648-76-1 exo-bicyclo[3.1.0]hexane-6-carboxylate methyl ester 
• 20047-45-4 exo-6-Methyl-bicyclo<3.1.0>hexan 

Relevant articles and documents

Concave reagents 32: Syn- and anti-selective cyclopropanation of alkenes with diazoacetates catalyzed by copper(I) complexes of concave 1,10- phenanthrolines

Two classes of concave 1,10-phenanthroline ligands 1 and 2 have been used in the copper(I) catalyzed cyclopropanation of several acyclic and cyclic alkenes 3 with three diazoacetates 4-6. The bimacrocyclic 2,9-diaryl- 1,10-phenanthrolines 1 favor the anti(trans- or exo-) cyclopropanation with anti/syn-selectivities of up to > 99:1 (8g). In contrast, with the 1,10- phenanthroline bridged calix[6]arenes 2 as ligands a rarely observed syn- selective cyclopropanation was achieved. Methyl diazoacetate (6) showed the best syn-selectivities with anti/syn-ratios of up to 14:86 (9g).

Cyclopropanation of alkenes with ethyl diazoacetate: Copper(I) complexes of concave 1,10-phenanthrolines as diastereoselective catalysts

Concave 1,10-phenanthrolines 1a-c have been used as ligands in the copper(I)-catalyzed cyclopropanation of alkenes 2 with ethyl diazoacetate. The complexes proved to be efficient cyclopropanation catalysts and exhibited an enhanced diastereoselectivity, particularly in the reactions of cyclic alkenes 2b-d. The preferred formation of exo-cyclopropanes 3b-d can be explained by the concave shape of these catalysts. VCH Verlagsgcsellschaft mbH.

Olefin cyclopropanation reactions catalysed by novel ruthenacarborane clusters

Novel ruthenacarborane clusters exhibit high activity as cyclopropanation catalysts in reactions between ethyl diazoacetate and alkenes.