94086-47-2

Basic information

• Product Name: 2-phenylpent-4-enoic acid
• Synonyms: 2-phenylpent-4-enoic acid
• CAS NO: 94086-47-2
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 176.21178
• EINECS: 301-835-6
• Mol File: 94086-47-2.mol

Chemical Properties

• Boiling Point: 288.7°Cat760mmHg
• Flash Point: 185.8°C
• Appearance: /
• Density: 1.086g/cm³
• Vapor Pressure: 0.00107mmHg at 25°C
• Refractive Index: 1.541
• CAS DataBase Reference: 2-phenylpent-4-enoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenylpent-4-enoic acid(94086-47-2)
• EPA Substance Registry System: 2-phenylpent-4-enoic acid(94086-47-2)

Safety Data

• Hazardous Substances Data: 94086-47-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H12O2/c1-2-6-10(11(12)13)9-7-4-3-5-8-9/h2-5,7-8,10H,1,6H2,(H,12,13)

Upstream product

• 1575-70-8 2-phenyl-pent-4-enoic acid 
• 5558-87-2 2-phenylpent-4-enenitrile 
• 34522-48-0 2-phenyl-4-pentenenamide 
• 91137-06-3 2-phenylpent-4-ynenitrile 
• 140-29-4 phenylacetonitrile 
• 1797-74-6 allyl phenylacetate 
• 103-82-2 phenylacetic acid 
• 106-95-6 allyl bromide 
• 104266-89-9 (S)-4-benzyl-3-phenylacetyl-2-oxazolidinone 
• 235097-99-1 (S)-4-benzyl-3-(2-phenylpent-4-enoyl)-2-oxazolidinone 
• 374590-14-4 1-((2R,5R)-2,5-Bis-methoxymethoxymethyl-pyrrolidin-1-yl)-2-phenyl-ethanone 
• 103-80-0 phenylacetyl chloride 
• 265656-11-9 (S)‐4‐benzyl‐3‐[(S)‐2‐phenylpent‐4‐enoyl]oxazolidin‐2‐one 
• 374590-15-5 (S)-1-((2R,5R)-2,5-Bis-methoxymethoxymethyl-pyrrolidin-1-yl)-2-phenyl-pent-4-en-1-one 

Downstream Products

• 7782-25-4 (S)-(+)-2-phenylvaleric acid 
• 374590-17-7 (S)-2-phenylpent-4-enoyl chloride 
• 5464-04-0 (R)-5-bromo-2-phenyl-valeric acid 
• 110658-37-2 (3R,5R)-5-Iodomethyl-3-phenyl-dihydro-furan-2-one 
• 1729-26-6 (3R,5S)-5-(iodomethyl)-3-phenyldihydrofuran-2(3H)-one 
• 56581-84-1 (R)-(-)-2-phenylglutaric acid 
• 104216-23-1 (R)-5-hydroxy-2-phenyl-valeric acid 
• 500721-74-4 (S)-2-phenyl-4-penteneamide 
• 235098-02-9 (S)-2-phenylpent-4-enoic acid,N-methyl amide 
• 374590-19-9 (2S,4S)-2-(2-Benzyloxy-ethyl)-1-((2S,5S)-2,5-bis-methoxymethoxymethyl-pyrrolidin-1-yl)-4-phenyl-hept-6-ene-1,3-dione 

Relevant articles and documents

Dual Activation of Unsaturated Amides with Schwartz's Reagent: A Diastereoselective Access to Cyclopentanols and N,O-Dimethylcyclopentylhydroxylamines.

The diastereoselective access to cyclopentanols and N,O-dimethylcyclopentylhydroxylamines from 4-pentenoic acid-derived Weinreb amides is described. Based on the concomitant generation of both the nucleophilic and the electrophilic poles by hydrozirconati

Uniting C1-Ammonium Enolates and Transition Metal Electrophiles via Cooperative Catalysis: The Direct Asymmetric α-Allylation of Aryl Acetic Acid Esters

The direct, catalytic, asymmetric α-functionalization of acyclic esters constitutes a significant challenge in the area of asymmetric catalysis, particularly where the configurational integrity of the products is problematic. Through the unprecedented mer

Enantioselective synthesis of levomilnacipran

A novel approach for the asymmetric synthesis of the active (1S,2R)-enantiomer of the antidepressant milnacipran is reported. The two stereogenic centers borne by the cyclopropane ring were sequentially installed starting from phenylacetic acid.

Highly enantioselective direct alkylation of arylacetic acids with chiral lithium amides as traceless auxiliaries

A direct, highly enantioselective alkylation of arylacetic acids via enediolates using a readily available chiral lithium amide as a stereodirecting reagent has been developed. This approach circumvents the traditional attachment and removal of chiral auxiliaries used currently for this type of transformation. The protocol is operationally simple, and the chiral reagent is readily recoverable.

Evidence for a non-concerted, dissoziative mechanism of the palladium-catalyzed enolate Claisen rearrangement of allylic esters

In an enolate Claisen rearrangement, deprotonated allyl phenylacetate undergoes a smooth conversion at -78 °C to 2-phenyl-4-pentenoic acid under palladium(O) catalysis. By using labelled starting materials in crossover experiments, the reaction is shown to follow a dissoziative, non-concerted, non-[3,3]-sigmatropic mechanism that involves palladium complexes and carboxylic-acid dianions as intermediates.

Remarkable electronic and steric effects in the nitrile biotransformations for the preparation of enantiopure functionalized carboxylic acids and amides: Implication for an unsaturated carbon-carbon bond binding domain of the amidase

(Chemical Equation Presented) Biotransformations of various functionalized racemic nitriles catalyzed by Rhodococcus erythropolis AJ270, a nitrile hydratase/amidase-containing microbial whole-cell catalyst, were studied. While the nitrile hydratase exhibi

Synthesis of enantiomerically enriched (S)-(+)-2-aryl-4-pentenoic acids and (R)-(-)-2-aryl-4-pentenamides via microbial hydrolysis of nitriles, a chemoenzymatic approach to stereoisomers of α,γ-disubstituted γ-butyrolactones

In the presence of the nitrile hydratase/amidase-containing Rhodococcus sp. AJ270 whole cell catalyst, 2-aryl-4-pentenenitriles 1 underwent enantioselective hydrolysis under mild conditions to afford (R)-(-)-2-aryl-4-pentenoic acid amides 2 and (S)-(+)-2-

Highly enantioselective biotransformations of 2-aryl-4-pentenenitriles, a novel chemoenzymatic approach to (R)-(-)-baclofen

Catalyzed by Rhodococcus sp. AJ270 microbial cells under mild conditions, a range of racemic 2-aryl-4-pentenenitriles 1 underwent effective hydrolysis to afford excellent yields of enantiomerically pure (R)-(-)-2-aryl-4-pentenamides 2 and (S)-(+)-2-aryl-4-pentenoic acids 3 in most cases. The application of this biotransformation has been shown by a two-step synthesis of (R)-(-)-baclofen.

A convenient synthesis of chiral β3-amino acids

A novel method for the synthesis of chiral β3-amino acids is developed where the acid functionality was built by oxidative cleavage of an α-allylic group that was introduced by Evans' asymmetric alkylation of an appropriate acid substrate and the amino part came from the amide of the original carboxyl group following a modified Hofmann rearrangement reaction.