40264-04-8

Usage

Uses

Used in Pharmaceutical Industry:
(1S,2S)-2-phenylcyclopentanamine serves as an intermediate in the synthesis of various pharmaceuticals, leveraging its unique stereochemistry and reactivity to produce compounds with specific therapeutic effects.
Used in Organic Synthesis:
As a chiral amine, (1S,2S)-2-phenylcyclopentanamine is utilized in organic synthesis to create enantiomerically pure compounds, which are essential in the development of drugs with targeted biological activity.
Used in Material Science:
(1S,2S)-2-phenylcyclopentanamine's structural properties allow it to be incorporated into the development of new materials with specialized properties, such as chiral catalysts or functional polymers, contributing to advances in material science.

Upstream product

• 825-54-7 cyclopent-1-en-1-ylbenzene 
• 477789-52-9 methyl-bis-(2-phenyl-cyclopentyl)borane 
• 1198-34-1 2-Phenylcyclopentanone 
• 542-92-7 cyclopenta-1,3-diene 
• 39203-22-0 di-tert-butyl 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate 
• 591-50-4 iodobenzene 
• 83849-01-8 2-phenylcyclopentan-1-one oxime 
• 477789-51-8 chloro-bis-(2-phenyl-cyclopentyl)borane 

Downstream Products

• 676464-29-2 (1S,2R)-2-phenylcyclopentanamine 
• 902458-04-2 trans-(1R,2S)-2-phenylcyclopentylamine 
• 676464-30-5 (1R,2S)-N-(2-phenylcyclopentyl)acetamide 

Relevant academic research and scientific papers

An exclusive approach to 3,4-disubstituted cyclopentenes and alkylidene cyclopentenes via the palladium catalyzed ring opening of azabicyclic olefins with aryl halides

A simple and efficient method for the stereoselective ring opening of bicyclic hydrazines with various aryl halides under palladium catalysis has been elaborated. The reactions afforded trans-3,4-disubstituted cyclopentenes or alkylidene cyclopentenes in good to excellent yields. By taking advantage of multiple points of functionalization in the synthesized trans-3-phenyl-4- hydrazino-cyclopentene, we have synthesized the antidepressant Cypenamine (trans-2-phenylcyclopentylamine).

Cyclopentyl sulfonamide derivatives

The present invention provides certain cyclopentyl sulfonamide derivatives of formula (I): useful for potentiating glutamate receptor function in a mammal. It also relates to novel cyclopentyl sulfonamide derivatives, to processes for their preparation and to pharmaceutical compositions containing them.

Design and synthesis of a novel series of 1,2-disubstituted cyclopentanes as small, potent potentiators of 2-amino-3-(3-hydroxy-5-methyl-isoxazol-4-yl)propanoic acid (AMPA) receptors

2-Amino-3-(3-hydroxy-5-methyl-isoxazol-4-yl)propanoic acid (AMPA) potentiators are ligands that act as positive allosteric modulators at the AMPA receptors. We recently disclosed a novel series of 2-arylpropylsulfonamides that were potent potentiators of responses mediated through AMPA receptors. To further define the structural requirements for activity in this series, new ring-constrained analogues were prepared and a new stereocenter was introduced. The potentiating activity was highly dependent on the stereochemistry at the 2-position of the disubstituted cyclopentane and was independent of the relative stereochemistry at the 1-position. Compound (R,R)-10 represents a potent, novel potentiator of iGluR4 flip receptors (EC50 = 22.6 nM).

ORGANOBORANES FOR SYNTHESIS. 7. AN IMPROVED GENERAL SYNTHESIS OF PRIMARY AMINES FROM ALKENES via HYDROBORATION-ORGANOBORANE CHEMISTRY

Triorganylboranes, R3B, and diorganylborinicesters, R2BOR', react readily with preformed chloramine or hydroxylamine-O-sulfonic acid to produce the corresponding primary amines, RNH2.However, the product of the reaction following hydrolysis is the boronic acid, RB(OH)2, limiting the yield to 67percent for R3B and to 50percent for R2BOR'.This problem has now been overcome with the help of lithium dimethylborohydride, readily converted in situ to dimethylborane.The hydroboration of representative alkenes by dimethylborane provides the corresponding monoorganyldimethylborane, RMe2B.Treatment of this intermediate with hydroxylamine-O-sulfonic acid provides the desired amines, RNH2, in isolated yields of 73percent to 95percent.The reaction proceeds with complete retention, reproducing the precise structure of the organic group in the organoboranes, RMe2B.