119271-86-2

Basic information

• Product Name: (Z)-4-phenylpent-3-enoic acid
• Synonyms: (Z)-4-phenylpent-3-enoic acid
• CAS NO: 119271-86-2
• Molecular Weight: 176.215
• Mol File: 119271-86-2.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (Z)-4-phenylpent-3-enoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-4-phenylpent-3-enoic acid(119271-86-2)
• EPA Substance Registry System: (Z)-4-phenylpent-3-enoic acid(119271-86-2)

Safety Data

• Hazardous Substances Data: 119271-86-2(Hazardous Substances Data)

Upstream product

• 141-82-2 malonic acid 
• 34713-70-7 2-Phenylpropanal 
• 223243-86-5 (E)-4-phenyl-3-pentenoic acid 
• 20047-26-1 4-Phenyl-(Z)-3-penten-1-ol 
• 98-86-2 acetophenone 
• 64-18-6 formic acid 
• 6051-52-1 2-phenylbut-3-en-2-ol 
• 201230-82-2 carbon monoxide 

Downstream Products

• 1252016-87-7 (Z)-4-phenyl-3-pentenoic acid phenyl amide 
• 950489-21-1 (R)-3-((Z)-4-phenylpent-3-enoyl)-4-phenyloxazolidin-2-one 

Relevant articles and documents

Direct palladium-catalyzed carbonylative transformation of allylic alcohols and related derivatives

A direct, palladium-catalyzed, carbonylative transformation of allylic alcohols for the synthesis of β,γ-unsaturated carboxylic acids has been developed. With formic acid as the CO source, various allylic alcohols were conveniently transformed into the corresponding β,γ-unsaturated carboxylic acids with excellent linear and (E)-selectivity. The reaction was performed under mild conditions; toxic CO gas manipulation and high-pressure equipment were avoided in this procedure.

Efficient Pd-Catalyzed Regio- and Stereoselective Carboxylation of Allylic Alcohols with Formic Acid

Formic acid is efficiently used as a C1 source to directly carboxylate allylic alcohols in the presence of a low loading of palladium catalyst and acetic anhydride as additive to afford β,γ-unsaturated carboxylic acids with excellent chemo-, regio-, and stereoselectivity. The reaction proceeds through a carbonylation process with in situ-generated carbon monoxide under mild conditions, avoiding the use of high-pressure gaseous CO. A bisphosphine ligand with a large bite angle (4,5-bis{diphenylphosphino}-9,9-dimethylxanthene, Xantphos) was found to be uniquely effective for this transformation. The regio- and stereoconvergence of this reaction is ascribed to the thermodynamically favored isomerization of the allylic electrophile in the presence of the palladium catalyst.

Remarkable levels of enantioswitching in catalytic asymmetric hydroboration

TADDOL-derived phosphites and phosphoramidites are effective ligands for rhodium-catalyzed asymmetric hydroborations of β,γ-unsaturated amides, achieving up to 99% ee. However, the sense of stereoinduction, R or S, is surprisingly dependent on rather subt