154278-40-7

Basic information

• Product Name: (1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl acetate
• Synonyms: (1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl acetate
• CAS NO: 154278-40-7
• Molecular Weight: 152.193
• Mol File: 154278-40-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl acetate(154278-40-7)
• EPA Substance Registry System: (1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl acetate(154278-40-7)

Safety Data

• Hazardous Substances Data: 154278-40-7(Hazardous Substances Data)

Upstream product

• 694-98-4 norborn-5-en-2-one 
• 694-97-3 endo-5-norbornen-2-ol 
• 292638-85-8 acrylic acid methyl ester 
• 63318-61-6 α-Aethoxyacrylsaeuremethylester 
• 2890-95-1 5-norbornenyl-2-acetate 

Downstream Products

• 202335-52-2 Toluene-4-sulfonic acid 2-((1S,4R)-4-propyl-cyclopent-2-enyl)-ethyl ester 
• 615249-16-6 Acetic acid (1S,2S,4R,6S)-6-hydroxy-bicyclo[2.2.1]hept-2-yl ester 
• 615249-17-7 (1S,4S,5R)-5-(4-Methoxy-benzyloxy)-bicyclo[2.2.1]heptan-2-one 
• 694-97-3 (1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-ol 
• 106928-44-3 (1R,2R,4R)-endo-bicyclo[2.2.1]hept-5-en-2-ol 
• 615249-19-9 (3aS,5S,6aR,8R,10aS)-5-[(1S,2R,3R,4R,5R)-3-Bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-4-methylene-octahydro-2-oxa-cyclopenta[d]naphthalen-3-one 
• 615249-03-1 (3aR,5R,6aS,8S,10aR)-5-[(1S,2R,3R,4R,5R)-3-Bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-4-methylene-octahydro-2-oxa-cyclopenta[d]naphthalen-3-one 
• 615249-20-2 C₃₅H₅₂O₇Si 
• 615249-28-0 C₃₃H₄₆O₅Si 
• 615249-36-0 C₂₉H₃₈O₇ 
• 615249-23-5 C₂₈H₃₁BrO₇ 
• 615249-29-1 C₂₉H₃₄O₆ 
• 615249-37-1 Acetic acid (3aR,4S,6aR,8S,10aR)-4-methyl-3,5-dioxo-4-((1R,2R,4S,6R)-3-oxo-6-phenyl-bicyclo[2.2.1]hept-2-yl)-decahydro-2-oxa-cyclopenta[d]naphthalen-8-yl ester 
• 615249-35-9 (1S,4S,5R)-2,2-Dimethoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]heptane 

Relevant articles and documents

Convenient Enzymatic Resolution of Alcohols Using Highly Reactive, Nonharmful Acyl Donors, 1-Ethoxyvinyl Esters

1-Ethoxyvinyl esters 3, a new type of acyl donors for enzymatic resolution of racemic alcohols, were disclosed to be superior to the contemporary major reagents, vinyl esters 1 and isopropenyl esters 2. Three features of 3 are noticeable: (1) 3 generates ethyl acetate as a single coproduct, which does not affect any enzymes, while acetaldehyde liberated from 1 deactivates some kinds of lipases. (2) The reactivity of 3 was not less than that of 1 and much higher than that of 2, and the optical purity of the products was as high as that of 1 and 2. Especially, it was generally observed that 3 showed higher reactivity than 1 for reactions using Candida rugosa lipases, one of the most commonly employed lipases, having liberal applicability to substrates but sensitive to acetaldehyde. Twelve examples of the kinetic resolution of racemic secondary alcohols (5 and 10) and one desymmetrization of meso-alcohol 7 were presented employing the acetate 3a or the octanoate 3b and four types of lipases. (3) A one-pot procedure for the preparation of 3 from the corresponding carboxylic acid and the subsequent enzymatic resolution of alcohols, which has not been reported using 1 or 2, was elucidated. The chemical and optical yields of the products by this procedure were similar to those obtained using isolated 3.

Stereoselectivity of 2-methyl-2-norpinyl cations

Optically active (1S)-1-methylbicyclo[2.2.1]heptan-2-one (25) was prepared by starting from (1R)-bicyclo[2.2.1]heptan-2-one (21). Photolysis of the tosylhydrazone 8 of 25 generates, in part, 1-methylbicyclo[2.2.1]heptane-endo-2-diazonium ions (10) from which 1-methylbicyclo[2.2.1]heptan-endo-2-ol (14) and 2-methylbicyclo[3.1.1]heptan-2-ol (16) arise. The ee of both products (42-45%) was found to agree within experimental error. These data point to the bridged 2-methyl-2-norpinyl cation (13) as the most stable structure. Racemization of 13 via the open 2-methyl-2-norpinyl cation (17) as the transition state competes with nucleophilic capture. VCH Verlagsgesellschaft mbH, 1996.