106928-44-3

Basic information

• Product Name: (R)-5-Norbornen-2-ol
• Synonyms: (R)-5-Norbornen-2-ol
• CAS NO: 106928-44-3
• Molecular Weight: 110.156
• Mol File: 106928-44-3.mol
• Article Data: 36

Chemical Properties

• CAS DataBase Reference: (R)-5-Norbornen-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-5-Norbornen-2-ol(106928-44-3)
• EPA Substance Registry System: (R)-5-Norbornen-2-ol(106928-44-3)

Safety Data

• Hazardous Substances Data: 106928-44-3(Hazardous Substances Data)

Upstream product

• 694-97-3 endo-5-norbornen-2-ol 
• 694-98-4 norborn-5-en-2-one 
• 2890-95-1 5-acetoxynorborn-2-ene 
• 154278-40-7 (1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl acetate 
• 292638-85-8 acrylic acid methyl ester 
• 108-05-4 vinyl acetate 
• 542-92-7 cyclopenta-1,3-diene 
• 18530-45-5 endo-5-Aminobicyclo[2.2.1]hept-2-ene 
• 278-06-8 quadricyclo[2.2.1.0.0]heptane 
• 16620-79-4 (-)-<1S,4S>bicyclo<2.2.1>heptene-5 one-2 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 51736-74-4 norborn-5-en-2-one 
• 22174-86-3 (1RS,2SR,4RS)-bicyclo<2.2.1>hept-5-en-2-yl butyrate 

Downstream Products

• 135583-74-3 (1S,2S,4R,5S,6S)-5-Chloro-6-phenylsulfanyl-bicyclo[2.2.1]heptan-2-ol 
• 135583-75-4 (1R,2R,4S,5S,6S)-6-Chloro-5-phenylsulfanyl-bicyclo[2.2.1]heptan-2-ol 
• 135560-46-2 exo-benzyl(bicyclo[2.2.1]hept-5-en-2-yl) ether 
• 57-13-6 urea 
• 833458-92-7 3-benzyl-3-aza-bicyclo[3.2.1]octan-6-one 
• 833459-00-0 3-(4-fluoro-phenyl)-3,4,9-triaza-tricyclo[5.3.1.02,6]undeca-2⁽⁶⁾,4-diene 
• 1383688-52-5 C₁₉H₁₈O 
• 497-38-1 (1S,4R)-bicyclo[2.2.1]heptan-2-one 

Relevant articles and documents

Effect of a remote substituent on regioselectivity in oxymercuration of unsymmetrically substituted norbornenes

The effect of a remote substituent on the regioselectivity in the oxymercuration of unsymmetrical substituted norbornenes has been investigated. Moderate to high levels of regioselectivity were observed with both exo- and endo-substituents at C-2 of norbornenes.

Bacillus stearothermophilus alcohol dehydrogenase: A new catalyst to obtain enantiomerically pure bicyclic octen- and hepten-ols and -ones

From the cells of Bacillus stearothermophilus a new enzyme has been isolated, which catalyses the stereospecific redox reactions of bicyclic octen- and hepten- ols and -ones.

Kinetic Resolution via Oxidation of endo-Bicyclic Octen- and Heptenols with Bacillus stearothermophilus

Key words: Kinetic resolution, Microbial oxidation, 6-endo-Bicyclohept-2-en-6-ol, 2-endo-Bicyclooct-7-en-2-ol, 2-endo-Norborn-5-en-2-ol Kinetic resolution of the racemic endo-bicyclic octenol and heptenols via oxidation with Bacillus stearothermopilus is described.The enantiomerically pure ketones and alcohols can be obtained varying the oxidation time.

Lactobacillus kefir Alcohol Dehydrogenase: A Useful Catalyst for Synthesis

The alcohol dehydrogenase from Lactobacillus kefir simultaneously catalyzes carbonyl reductions and NADPH regeneration in the presence of 2-propanol.Representative synthesis of a number of chiral alcohols was accomplished in good yield and high enantiomeric excess (94-99percent).This NADPH-requiring enzyme transfers the pro-R hydride from the cofactor to the si face of carbonyls to give (R) alcohols.The enzyme exhibits a very broad substrate specificity and high enantioselectivity for the synthesis of chiral aromatic, cyclic, polycyclic, and aliphatic alcohols.

'Immunization' of Lipase against Acetaldehyde emerging in Acyl Transfer Reactions from Vinyl Acetate

Immobilization of Candida cylindracea lipase by covalent linkage involving the ε-amino residues of lysine leads to a five-fold increase of selectivity which is entirely preserved against deactivation caused by acetaldehyde, an unavoidable by-product in acyl transfer reactions with vinyl acetate.

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Large scale preparation of (+)- and (-)-endo-norbornenol by enzymatic hydrolysis

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Alkylhalovinylboranes: a new class of Diels-Alder dienophiles

The Diels-Alder reactions of alkylhalovinylboranes have been investigated theoretically and experimentally. Alkylhalovinylboranes presented higher reactivity than the corresponding dialkylvinylboranes. Although endo/exo selectivities were high for the reactions with cyclopentadiene, facial selectivities for the chiral analogues were low. Our results demonstrate that the replacement of an alkyl group on the boron atom by a halogen increases the dienophilicity considerably.

A facile microwave-assisted Diels-Alder reaction of vinylboronates

The Diels-Alder reaction of vinylboronates can be easily performed using microwave irradiation giving excellent yields of the cycloadducts. Pinacol vinylboronate was the reagent of choice due to its stability towards hydrolysis, operational simplicity and yields of Diels-Alder products. To the best of our knowledge, this is the first example of microwave-assisted Diels-Alder reaction of boron-substituted dienophiles. Subsequent in situ oxidation of the cycloadducts with alkaline hydrogen peroxide afforded the alcohols efficiently.