132203-22-6

Basic information

• Product Name: (R,E)-3-hydroxy-5-phenylpent-4-enenitrile
• Synonyms: (R,E)-3-hydroxy-5-phenylpent-4-enenitrile
• CAS NO: 132203-22-6
• Molecular Weight: 173.214
• Mol File: 132203-22-6.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: (R,E)-3-hydroxy-5-phenylpent-4-enenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (R,E)-3-hydroxy-5-phenylpent-4-enenitrile(132203-22-6)
• EPA Substance Registry System: (R,E)-3-hydroxy-5-phenylpent-4-enenitrile(132203-22-6)

Safety Data

• Hazardous Substances Data: 132203-22-6(Hazardous Substances Data)

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 75-05-8 acetonitrile 
• 147976-19-0 (4S)-2,2-dimethyl-4-[(E)-2-phenylethenyl]-1,3-dioxolane 
• 152203-66-2 (E)-(S)-4-Phenyl-but-3-ene-1,2-diol 
• 152203-65-1 (4S)-2,2-dimethyl-4-styryl-1,3-dioxolane 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 151-50-8 potassium cyanide 
• 4192-77-2 ethyl cinnamate 
• 140-10-3 (E)-3-phenylacrylic acid 
• 1446698-46-9 (dimethylsilyl)acetonitrile 
• 64307-20-6 (4E)-3-oxo-5-phenyl-4-pentenenitrile 
• 104-55-2 3-phenyl-propenal 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 57194-69-1 cinnamaldehyde 

Downstream Products

• 917251-11-7 (3R,4E)-3-(tert-butyldimethylsilanyloxy)-5-phenylpent-4-enal 
• 917251-12-8 (5R,2Z,6E)-5-(tert-butyldimethylsilanyloxy)-7-phenylhepta-2,6-dienoate 
• 917251-13-9 (R,2Z,6E)-5-hydroxy-7-phenylhepta-2,6-dienoate 
• 356793-34-5 (E)-(R)-5-Hydroxy-3-oxo-7-phenyl-hept-6-enoic acid methyl ester 

Relevant articles and documents

Direct Catalytic Asymmetric Addition of Alkylnitriles to Aldehydes with Designed Nickel–Carbene Complexes

A direct catalytic asymmetric addition of acetonitrile to aldehydes that realizes over 90 % ee is the ultimate challenge in alkylnitrile addition chemistry. Herein, we report achieving high enantioselectivity by the strategic use of a sterically demanding NiII pincer carbene complex, which afforded highly enantioenriched β-hydroxynitriles. This highly atom-economical process paves the way for exploiting inexpensive acetonitrile as a promising C2 building block in a practical synthetic toolbox for asymmetric catalysis.

Synthesis of Functionalized Benzo[b]furans via Oxidative Cyclization of o-Cinnamyl Phenols

Disclosed herein is an efficient synthetic route for the synthesis of functionalized 2-benzyl benzo[b]furans via a regioselective 5-exo-trig intramolecular oxidative cyclization of ortho-cinnamyl phenols using [PdCl2(CH3CN)2] as catalyst and benzoquinone as an oxidant. Further, a sequential ortho-cinnamylation of phenols using cinnamyl alcohols catalyzed by Re2O7, followed by an oxidative cyclization using the above Pd catalyst, is performed. The reaction showed broad substrate scope with good to excellent yields.

N-Heterocyclic carbene-catalyzed cyanomethylation of aldehydes with TMSAN

N-Heterocyclic carbenes (NHCs) have been served as efficient catalysts for cyanomethylation of carbonyl compounds. In the presence of 5 mol % NHC, various aldehydes and 2,2,2-trifluoroacetophenone reacted with trimethylsilylacetonitrile (TMSAN) to give β-hydroxynitriles in moderate to high yields.