768-48-9

Basic information

• Product Name: 4-Acetoxy-2-cyclopenten-1-one
• Synonyms: 4-Acetoxy-2-cyclopenten-1-one;4-OXOCYCLOPENT-2-ENYL ACETATE
• CAS NO: 768-48-9
• Molecular Formula: C₇H₈O₃
• Molecular Weight: 140.13662
• Mol File: 768-48-9.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 223 °C at 760 mmHg
• Flash Point: 92 °C
• Appearance: /
• Density: 1.16 g/cm³
• Vapor Pressure: 0.0987mmHg at 25°C
• Refractive Index: 1.481
• CAS DataBase Reference: 4-Acetoxy-2-cyclopenten-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Acetoxy-2-cyclopenten-1-one(768-48-9)
• EPA Substance Registry System: 4-Acetoxy-2-cyclopenten-1-one(768-48-9)

Safety Data

• Hazardous Substances Data: 768-48-9(Hazardous Substances Data)

Usage

Description

4-Acetoxy-2-cyclopenten-1-one, also known as acetyl cyclopentenone, is a chemical compound with the molecular formula C7H8O3. It is a cyclic enol ether with a five-membered ring structure, known for its characteristic sweet, floral odor. 4-Acetoxy-2-cyclopenten-1-one is highly reactive and is typically handled with caution due to its flammability and potential for causing skin and eye irritation.

Uses

Used in Pharmaceutical Industry:
4-Acetoxy-2-cyclopenten-1-one is used as a building block in organic synthesis for the production of various pharmaceuticals. It serves as a key intermediate in the synthesis of natural products with diverse biological activities, making it a valuable component in the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical industry, 4-Acetoxy-2-cyclopenten-1-one is used as a starting material for the synthesis of various agrochemicals. Its versatility allows for the creation of compounds with potential applications in pest control and crop protection.
Used in Fragrance Industry:
Due to its sweet, floral odor, 4-Acetoxy-2-cyclopenten-1-one is used as a fragrance ingredient in the perfumery and cosmetics industry. Its unique scent profile contributes to the creation of various fragrances and scents in a wide range of products.

InChI:InChI=1/C7H8O3/c1-5(8)10-7-3-2-6(9)4-7/h2-3,7H,4H2,1H3

Upstream product

• 59995-47-0 4-Hydroxycyclopent-2-enone 
• 108-24-7 acetic anhydride 
• 108-05-4 vinyl acetate 
• 60895-01-4 3(S)-acetoxy-5-(R)-hydroxy-cyclopent-1-ene 
• 116195-10-9 3-tert-Butoxy-4-<<(exo-2'-hydroxy-7',7'-dimethylbicyclo<2.2.1>heptanyl)methyl>thio>cyclopentanone 
• 930-60-9 maleic anhydride 
• 98-00-0 (2-furyl)methyl alcohol 
• 765-56-0 4-bromocyclopent-2-enone 
• 64-19-7 acetic acid 
• 73448-15-4 4-tert-butoxycyclopent-2-en-1-one 
• 930-30-3 cyclopent-2-enone 

Downstream Products

• 108886-63-1 11-cis-5-methyl-4-<1-methyl-3-(2,6,6-trimethylcyclohex-1-enyl)prop-2-enylidene>cyclopent-2-enylidene-acetaldehyde 
• 59995-47-0 4-Hydroxycyclopent-2-enone 
• 237765-99-0 3-allyl-2-<1-hydroxy-4-acetoxycyclopent-2-enyl>cyclopent-4-enone 

Relevant articles and documents

Highly Reactive and Tracelessly Cleavable Cysteine-Specific Modification of Proteins via 4-Substituted Cyclopentenone

A rapid and cysteine-specific modification of proteins using 4-substituted cyclopentenone via a Michael addition tandem elimination reaction was developed. Compared to the classical method, this reaction featured fast kinetics with a stable product. More importantly, this conjugation could be tracelessly removed by exchange with a Michael addition donor. The conjugation and regeneration process not only exhibited little change to the structures or conformations of the proteins but also exhibited little disturbance to their biological functions, such as their enzymatic activities.

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.