25209-52-3

Basic information

• Product Name: (1-hydroxycyclopentyl)phenylacetic acid
• Synonyms: (1-hydroxycyclopentyl)phenylacetic acid;α-(1-Hydroxycyclopentyl)benzeneacetic acid
• CAS NO: 25209-52-3
• Molecular Formula: C₁₃H₁₆O₃
• Molecular Weight: 220.26434
• EINECS: 246-733-1
• Mol File: 25209-52-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 384.3°Cat760mmHg
• Flash Point: 200.4°C
• Appearance: /
• Density: 1.263g/cm³
• Vapor Pressure: 1.36E-06mmHg at 25°C
• Refractive Index: 1.603
• CAS DataBase Reference: (1-hydroxycyclopentyl)phenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1-hydroxycyclopentyl)phenylacetic acid(25209-52-3)
• EPA Substance Registry System: (1-hydroxycyclopentyl)phenylacetic acid(25209-52-3)

Safety Data

• Hazardous Substances Data: 25209-52-3(Hazardous Substances Data)

Usage

Uses

1-Hydroxy-α-Phenylcyclopentaneacetic Acid is used in the preparation of oxazolidinone compounds and derivatives thereof as inhibitors of tankyrase. Its also an impurity of Cyclopentolate(C986405) a muscarinic antagonist.

Definition

ChEBI: (1-hydroxycyclopentyl)acetic acid in which one of the hydrogens alpha to the carboxylic acid group is substituted by a phenyl group.

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 4221, 1951 DOI: 10.1021/ja01153a053

InChI:InChI=1/C13H16O3/c14-12(15)11(10-6-2-1-3-7-10)13(16)8-4-5-9-13/h1-3,6-7,11,16H,4-5,8-9H2,(H,14,15)

Upstream product

• 78853-39-1 Cyclodrinhydrochlorid 
• 95777-19-8 phenylacetic acid magnesium enediolate 
• 120-92-3 cyclopentanone 
• 103-82-2 phenylacetic acid 
• 114-70-5 sodium phenylacetate 
• 920-39-8 isopropylmagnesium bromide 

Downstream Products

• 1456507-21-3 4-phenyl-1-oxa-3-azaspiro[4.4]nonan-2-one 
• 1456505-13-7 (R+S) 4-(2-oxo-4-phenyl-1-oxa-3-azaspiro[4.4]nonan-3-yl)-N-(quinolin-8-yl)benzamide 
• 25115-73-5 2-(4-chlorophenyl)cyclohexanone 
• 512-15-2 Cyclopentolate 
• 52109-93-0 (1-hydroxy-cyclopentyl)-phenyl-acetic acid-(2-diethylamino-ethyl ester) 
• 55930-33-1 N-Hydroxy-2-(1-hydroxy-cyclopentyl)-2-phenyl-acetamide 
• 4410-77-9 benzylidenecyclopentane 
• 126497-27-6 2-cyclopentylidene-1-phenylacetic acid 
• 752943-22-9 (1-hydroxy-cyclopentyl)-phenyl-acetic acid-(2-piperidino-ethyl ester) 

Relevant articles and documents

Stereospecific Electrophilic Fluorocyclization of α,β-Unsaturated Amides with Selectfluor

An efficient fluorocyclization of α,β-unsaturated amides through a formal halocyclization process is developed. The reaction proceeds under transition-metal-free conditions and leads to the formation of fluorinated oxazolidine-2,4-diones with excellent regio- and diastereoselectivity. The evaluation of the reaction mechanism based on preliminary experiments and density functional theory calculations suggests that a synergetic syn-oxo-fluorination occurs and is followed by an anti-oxo substitution reaction. The reaction opens a new window in the field of stereospecific fluorofunctionalization.

Preparation method of cyclopentolate hydrochloride

The invention relates to a preparation method of an M-type cholinoceptor blocker cyclopentolate hydrochloride. The preparation method comprises that phenylacetic acid as an initial raw material and cyclopentanone undergoes a reaction to produce 2-(1-hydroxycyclopentyl)-phenylacetic acid (as intermediate 3), the 2-(1-hydroxycyclopentyl)-phenylacetic acid undergoes a replacement reaction and the reaction product undergoes a salification reaction to produce cyclopentolate hydrochloride. The preparation method can be operated simply, is safe and controllable, has low labor protection demands and is suitable for industrial production.

Kinetics and Mechanism of the Ivanov Reaction: Reaction of Aldehydes and Ketones with Phenylacetic Acit Magnesium Enediolate

Stopped-flow kinetics of the reaction between aldehydes or ketones and the magnesium enediolate of phenylacetic acid in THF are second order at enediolate concentrations -3 M.At concentrations of 10-3 - 3*10-2 M, the formation of a bis(enediolate) requires a more complex kinetic equation.Second-order rate constans are reported for the reaction of the enediolate with a number of aldehydes and ketones at 25 deg C.Entropies of activation for cyclohexanone, benzaldehyde, 2-methylpropanal, and 2,2-dimethylpropanal are positive, and enthalpy-entropy compensation is observed.Ef fects of cycloalkanone ring size and benzaldehyde substituents are small and are ascribable to a transition state with a very small C-C bond order.A two-step mechanism is proposed, with preequilibrium formation of a coordination intermediate which, in some cases, is accompanied by a change in the magnesium coordination number.Effects of alkyl groups on aldehyde and ketone reactivity stem mainly from steric desolvation.