59995-50-5

Basic information

• Product Name: 2-Cyclopenten-1-one, 4-(acetyloxy)-, (S)-
• CAS NO: 59995-50-5
• Molecular Formula: C7H8O3
• Molecular Weight: 140.139
• Mol File: 59995-50-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Cyclopenten-1-one, 4-(acetyloxy)-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclopenten-1-one, 4-(acetyloxy)-, (S)-(59995-50-5)
• EPA Substance Registry System: 2-Cyclopenten-1-one, 4-(acetyloxy)-, (S)-(59995-50-5)

Safety Data

• Hazardous Substances Data: 59995-50-5(Hazardous Substances Data)

Usage

General Description

2-Cyclopenten-1-one, 4-(acetyloxy)-, (S)- is a chemical compound with the molecular formula C8H10O3. It is a chiral molecule, with the (S)-enantiomer being the biologically active form. 2-Cyclopenten-1-one, 4-(acetyloxy)-, (S)- is commonly known as levofloxacin, which is an antibiotic used to treat bacterial infections. It works by inhibiting the bacterial enzyme DNA gyrase, thereby preventing the replication and repair of bacterial DNA. Levofloxacin is commonly prescribed for respiratory tract infections, urinary tract infections, and skin infections caused by susceptible bacteria. It is available in various forms, including oral tablets, oral solutions, and intravenous infusions. However,

Upstream product

• 108-05-4 vinyl acetate 
• 59995-47-0 4-Hydroxycyclopent-2-enone 
• 86-55-5 1-naphthalenecarboxylic acid 
• 768-48-9 4-acetoxy-cyclopentenone 
• 108-95-2 phenol 
• 108-24-7 acetic anhydride 
• 61305-37-1 (S)-4-tetrahydropyranyloxy-2-cyclopenten-1-one 
• 59995-47-0 (R)-(+)-4-hydroxy-2-cyclopentenone 

Relevant articles and documents

4-Heterosubstituted Cyclopentenone Antiviral Compounds: Synthesis, Mechanism, and Antiviral Evaluation

Racemic 4-oxocyclopent-2-en-1-yl acetate was used in a short synthesis of nucleoside analogues with pyrimidine and purine heterobases. The protocol is based on a typical nucleophilic substitution process. Uracil, thymine, 6-chloropurine, and some adenines gave the expected 4-heterosubstituted products along with the isomeric 2-heterosubstituted compounds as minor components. Samples of selected products were evaluated for their antiviral activity in a primary screening against a variety of viruses belonging to different classes. One of the compounds was found to be highly active against human papilloma virus (HPV).

Enzymatic kinetic resolution studies of racemic 4-hydroxycyclopent-2-en- 1-one using Lipozyme IM

Enzymatic kinetic resolution studies of (±)-4-hydroxycyclopent-2-en-1- one 2 were taken up in organic solvents by transesterification with vinyl acetate and alcoholysis of its acetate 3 as an alternative to the desymmetrization of meso-cyclopentenediol to provide faster and economic access to enantiomerically pure 4-(R)-tert-butyldimethylsilyloxycyclopent-2- en-1-one 1. Parameters were screened using Lipozyme IM as catalyst. Although enantioselectivity observed was moderate (E=24, by alcoholysis of 3 with 2-butanol), trends in the effect of solvent, water content and alcohol structure showed useful directions for screening of other enzymes for optimization of the method to useful levels of efficiency.

AN ASYMMETRIC SYNTHESIS OF CIS-4-t-BUTYLDIMETHYLSILOXY-2-CYCLOPENTEN-1-OL AND CIS-4-TETRAHYDROPYRANYLOXY-2-CYCLOPENTEN-1-OL, VERSATILE CHIRAL SYNTHETIC INTERMEDIATE FOR PROSTANOIDS

cis-4-t-Butyldimethylsiloxy-2-cyclopenten-1-ol and cis-4-tetrahydropyranyloxy-2-cyclopenten-1-ol were obtained with high enantiomeric excesses (ee) by the reaction of cis-3,4-epoxycyclopentan-1-ol derivatives with chiral lithium amide.An application to the syntheses of both (S)- and (R)-4-hydroxy-2-cyclopentenone was demonstrated.