90719-45-2

Basic information

• Product Name: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, phenylmethyl ester, (1R,2R,4R)-
• CAS NO: 90719-45-2
• Molecular Formula: C15H16O2
• Molecular Weight: 228.291
• Mol File: 90719-45-2.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, phenylmethyl ester, (1R,2R,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, phenylmethyl ester, (1R,2R,4R)-(90719-45-2)
• EPA Substance Registry System: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, phenylmethyl ester, (1R,2R,4R)-(90719-45-2)

Safety Data

• Hazardous Substances Data: 90719-45-2(Hazardous Substances Data)

Upstream product

• 131564-05-1 3-[(1R,2R,4R)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]oxazolidin-2-one 
• 100-51-6 benzyl alcohol 
• 90719-33-8 (4S)-3-((3'R,4'R,6'R)-bicyclo[2.2.1]heptene-4'-carbonyl)-4-(1-methylethyl)-2-oxazolidinone 
• 77-73-6 bi(cyclopentadiene) 
• 2495-35-4 benzylacrylate 
• 542-92-7 cyclopenta-1,3-diene 
• 15082-42-5 lithium benzyloxide 
• 90719-34-9 (4S)-3-((3'R,4'R,6'R)-bicyclo[2.2.1]heptene-4'-carbonyl)-4-(phenylmethyl)-2-oxazolidinone 
• 120-74-1 5-carboxybicyclo<2.2.1>hept-2-ene 
• 100-39-0 benzyl bromide 
• 120-74-1 endo-norbornenecarboxylic acid 

Downstream Products

• 145117-47-1 (1R,2R,4R,5S)-5-Acetoxy-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester 
• 145117-46-0 (1S,2R,4R,6R)-6-Acetoxy-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester 

Relevant articles and documents

Oxathiaborolium-Catalyzed Enantioselective [4 + 2] Cycloaddition and Its Application in Lewis Acid Coordinated and Chiral Lewis Acid Catalyzed [4 + 2] Cycloaddition

The nascency of second-generation sulfur-stabilized borenium cations by halophilic Lewis acid SnCl4 leads to highly active chiral Lewis acids that are very effective catalysts for [4 + 2] cycloaddition. Oxathiaborolium pentachlorostannate (5-10 mol %) successfully catalyzed cycloaddition of various dienes and dienophiles to afford cycloadducts with excellent enantioselectivity (20 examples, up to 99% ee). This super Lewis acid also exhibited good enantioselectivity for the first Lewis acid coordinated and chiral Lewis acid catalyzed [4 + 2] cycloaddition to α,β-unsaturated mixed ester amide.

Oxathiaborolium: A type of chiral Lewis acid catalyst and its application in catalytic and highly enantioselective Diels-Alder reactions

The first reported sulfur-stabilized borenium cations were synthesized through halide abstraction of a haloborane intermediate by halophilic reagents. Different from the well-known cationic oxazaborolidines, a sulfide instead of an amine was used to not only simplify the preparation of the catalysts but also increase Lewis acidity of the boron atom. The in situ generated borenium salts showed exceptional Lewis acidity and successfully catalyzed asymmetric Diels-Alder reactions of cyclopentadiene and dienophiles in excellent yields and enantioselectivities. The NMR studies of these oxathiaborolium structures were reported as well.

Molecular imprinted polymers binding low functionality templates

A series of highly specific molecular imprinted polymers (MIPs) for small, low functionality bicyclic Diels-Alder products was prepared as bulk polymers.