25209-52-3

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

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

Downstream Products

• 4410-77-9 benzylidenecyclopentane 
• 55930-33-1 N-Hydroxy-2-(1-hydroxy-cyclopentyl)-2-phenyl-acetamide 
• 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) 
• 126497-27-6 2-cyclopentylidene-1-phenylacetic acid 
• 752943-22-9 (1-hydroxy-cyclopentyl)-phenyl-acetic acid-(2-piperidino-ethyl ester) 

Relevant academic research and scientific papers

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 intermediate

The invention belongs to the technical field of pharmaceutical chemicals, and relates to a preparation method of a cyclopentolate hydrochloride intermediate. Methyl phenylacetate is used as a raw material, the price is low, the methyl phenylacetate is commercially produced, the goods source is sufficient, and the quality is stable. The commercially available Grignard reagent is adopted, so that the risk that flammable and explosive reagents are used and are not controlled when the Grignard reagent is self-made is avoided. Commercially available Grignard reagents have been industrially produced and are convenient and easy to obtain. And the intermediate is purified by adopting a crystallization solvent, so that the purity of the intermediate is ensured, the preparation yield of the cyclopentolate hydrochloride is increased, and subsequent crystallization and impurity removal processes are reduced. And the production risk and the labor protection requirement of workers are reduced, environmental protection is facilitated, and the economic benefit is improved. The yield of phenylacetic acid can reach 95% or above, the purity of phenylacetic acid can reach 99.9% or above, the production requirements of the cyclopentolate hydrochloride intermediate are completely met, and the yield and purity of the product 2-(1-hydroxycyclopentyl)-phenylacetic acid are much higher than those of 2-(1-hydroxycyclopentyl)-phenylacetic acid produced by a common method.

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.

OXAZOLIDINONE COMPOUNDS AND DERIVATIVES THEREOF

Compounds of Formula (I) and Formula (II) are useful inhibitors of tankyrase. Compounds of Formula (I) and Formula (II) have the following structure: where the definitions of the variables are provided herein.

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.

Contribution to the Stability of Cyclodrin Hydrochloride. Part 1: The Mechanism of Degradation of Cyclodrin Hydrochloride and the Detection of Its Degradation Products in the Presence of the Intact Active Agent

The mechanism of degradation of cyclodrin hydrochloride was elucidated.For this purpose, methods were divised which permit to determine the intact active agent in the presence of its degradation products.The simultaneous use of different solvent systems for the separation of the substances as well as utilization of several revealing reagents of varying specificity justify the conclusion that no further degradation products are formed.Attempts to detect the cyclopentyl residue (which is presumably released in the form of cyclopentanol during the cleavage of α-(1-hydroxycyclopentyl) phenyl acetic acid) failed.