189625-12-5

Basic information

• Product Name: [(1R,4S)-4-HYDROXY-2-CYCLOPENTEN-1-YL]CARBAMIC ACID, 1,1-DIMETHYLETHYL ESTER
• Synonyms: (1R,4S)-4-HYDROXY-1-N-TERT-BUTOXYCARBOXY-2-CYCLOPENTENAMINE;[(1R,4S)-4-HYDROXY-2-CYCLOPENTEN-1-YL]CARBAMIC ACID, 1,1-DIMETHYLETHYL ESTER;Carbamic acid, [(1R,4S)-4-hydroxy-2-cyclopenten-1-yl]-, 1,1-dimethylethyl;[(1R,4S)-4-Hydroxy-2-cyclopenten-1-yl]carbamic acid tert-butyl ester;(1R,4S)-4-hydroxy-1-n-tertbutoxycarboxy-,2-cyclope;(1R,4S)-(4-Hydroxy-cyclopent-2-enyl)-carbamic acid tert-butyl ester;tert-butyl N-[(1R,4S)-4-hydroxycyclopent-2-en-1-yl]carbamate;tert-Butyl ((1R,4S)-4-hydroxycyclopent-2-en-1-yl)carbamate
• CAS NO: 189625-12-5
• Molecular Formula: C₁₀H₁₇NO₃
• Molecular Weight: 199.25
• Product Categories: N-BOC
• Mol File: 189625-12-5.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [(1R,4S)-4-HYDROXY-2-CYCLOPENTEN-1-YL]CARBAMIC ACID, 1,1-DIMETHYLETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: [(1R,4S)-4-HYDROXY-2-CYCLOPENTEN-1-YL]CARBAMIC ACID, 1,1-DIMETHYLETHYL ESTER(189625-12-5)
• EPA Substance Registry System: [(1R,4S)-4-HYDROXY-2-CYCLOPENTEN-1-YL]CARBAMIC ACID, 1,1-DIMETHYLETHYL ESTER(189625-12-5)

Safety Data

• Hazardous Substances Data: 189625-12-5(Hazardous Substances Data)

Usage

General Description

The chemical compound [(1R,4S)-4-hydroxy-2-cyclopenten-1-yl]carbamic acid, 1,1-dimethylethyl ester is a carbamate ester that is commonly used as a pesticide and insecticide. It is derived from the natural compound cyclopentenol, and its hydroxy group makes it an effective inhibitor of acetylcholinesterase, an enzyme essential for nerve impulse transmission. [(1R,4S)-4-HYDROXY-2-CYCLOPENTEN-1-YL]CARBAMIC ACID, 1,1-DIMETHYLETHYL ESTER is known for its strong toxicity to insects and other pests, and is used in agricultural and horticultural applications to protect crops from damage. Additionally, it has also been studied for its potential use in pharmaceuticals due to its inhibition of acetylcholinesterase and potential neuroprotective effects.

Upstream product

• 189625-14-7 (2S,4R)-acetic acid 4-tert-butoxycarbonylaminocyclopent-2-enyl ester 
• 657397-01-8 (2R)-(4-oxocyclopent-2-enyl)-carbamic acid tert-butyl ester 
• 108-05-4 vinyl acetate 
• 657396-96-8 (4-hydroxycyclopent-2-enyl)-carbamic acid tert-butyl ester 
• 220241-57-6 di-tert-butyl [(1R,4S)-4-hydroxycyclopent-2-en-1-yl]imidodicarbonate 
• 51779-32-9 iminodicarboxylic acid di-tert-butyl ester 
• 60410-16-4 (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 667457-57-0 (R)-(-)-N-(tert-butoxycarbonyl)-6-amino-4-oxo-octa-2,7-diene 
• 667457-58-1 (R)-(-)-N-(tert-butoxycarbonyl)-6-amino-4-oxo-nona-2,7-diene 
• 667457-53-6 (S_S,R)-(+)-N-(p-toluenesulfinyl)-6-amino-4-oxo-octa-2,7-diene 
• 667457-54-7 (S_S,R)-(+)-N-(p-toluenesulfinyl)-6-amino-4-oxo-nona-2,7-diene 
• 667457-51-4 (S_S,R)-(+)-dimethyl [2-oxo-4-(p-toluenesulfinylamino)-hex-5-enyl]-phosphonate 
• 667457-52-5 (S_S,R)-(+)-dimethyl [2-oxo-4-(p-toluenesulfinylamino)-hept-5-enyl]-phosphonate 

Downstream Products

• 189625-14-7 (2S,4R)-acetic acid 4-tert-butoxycarbonylaminocyclopent-2-enyl ester 
• 657397-01-8 (2R)-(4-oxocyclopent-2-enyl)-carbamic acid tert-butyl ester 
• 657397-03-0 (2R,4S)-acetic acid 4-tert-butoxycarbonylaminocyclopent-2-enyl ester 
• 1092096-28-0 (1R, 4R)-4-[(tert-butoxycarbonyl)amino]-2-cyclopenten-1-yl 4-nitrobenzoate 

Relevant articles and documents

Asymmetric synthesis of cis-aminocyclopentenols, building blocks for medicinal chemistry

A highly efficient one-pot multistep process involving an asymmetric Pd(II)-catalyzed Overman rearrangement and a Ru(II)-catalyzed ring-closing metathesis reaction has been developed for the preparation of (R)- or (S)-aminocyclopenta-2-enes. The rapid strategy employed and the relatively mild conditions of the one-pot process allowed the multigram synthesis of the carbocycles in high enantiomeric excess (92% ee). The synthetic utility of these compounds was demonstrated by the stereoselective incorporation of hydroxyl groups, generating cis-4- and cis-5-aminocyclopenta-2-en-1-ols, important building blocks for medicinal chemistry.

Total synthesis of (-)-agelastatin A

(Chemical Equation Presented) A new route to (-)-agelastatin A is reported. The requisite nitrogen functionalities of the agelastatin core have been installed by intramolecular aziridination of an azidoformate and subsequent regioselective azidation, lead

Synthesis of 4-azacyclopent-2-enones and 5,5-dialkyl-4-azacyclopent-2- enones

Three different methods are reported for the preparation of 4-azacyclo-2-enones 1, two of which allow the preparation of the compounds in optically active form. In addition, a facile route to 4-aza-5,5- dimethylcyclopent-2-enones 2 is disclosed.