198022-60-5

Basic information

• Product Name: (+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid
• Synonyms: (+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid
• CAS NO: 198022-60-5
• Molecular Weight: 286.328
• Mol File: 198022-60-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid(198022-60-5)
• EPA Substance Registry System: (+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid(198022-60-5)

Safety Data

• Hazardous Substances Data: 198022-60-5(Hazardous Substances Data)

Usage

Description

(+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid is a complex chiral chemical compound characterized by a cyclopentane ring, a carboxylic acid group, and a (1S,2R) configuration. It features a methylene group, a propenyl oxycarbonyl group, and a phenyl group, which may contribute to its potential bioactivity and interest in medicinal chemistry and drug discovery.

Uses

Used in Medicinal Chemistry:
(+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid is used as a bioactive compound for its potential applications in medicinal chemistry. Its unique structure and chirality may offer specific interactions with biological targets, making it a candidate for the development of new drugs.
Used in Drug Discovery:
In the field of drug discovery, (+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid is utilized as a lead compound. Its complex structure and chiral nature could be exploited to design and optimize new pharmaceutical agents targeting various diseases and conditions.
Used in Pharmaceutical Industry:
(+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid is used as a chemical intermediate in the pharmaceutical industry. Its synthesis and modification can lead to the production of new drug molecules with improved efficacy and selectivity.
Used in Research and Development:
(+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid is employed as a research tool in academic and industrial laboratories. Its study can provide insights into the structure-activity relationships of bioactive compounds and contribute to the advancement of medicinal chemistry.

Upstream product

• 90474-14-9 4-Methylene-cyclopentane-1,2-dicarboxylic acid 
• 6261-04-7 2,3,4-tris(ethoxycarbonyl)cyclopentanone 
• 1703-61-3 rac-4-oxocyclopentane-1,2-dicarboxylic acid 
• 914637-96-0 diethyl 4-oxo-1,2-cyclopentanedicarboxylate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 139228-09-4 5-methylenetetrahydrocyclopenta[c]furan-1,3-dione 
• 343956-49-0 4-Methylene-cyclopentane-1,2-dicarboxylic acid diethyl ester 
• 4373-15-3 1,2,3,4-butanetetracarboxylic acid tetraethyl ester 
• 4534-68-3 1,2,3,4-butanetetracarboxylic acid 

Downstream Products

• 198022-62-7 (2E)-3-phenyl-2-propenyl (1R,2S)-4-methylene-2-{[(2E)-3-phenyl-2-propenyloxycarbonyl]amino}cyclopentanecarboxylate 
• 198022-65-0 (-)-(1R,2S)-2-amino-4-methylenecyclopentanecarboxylic acid 

Relevant articles and documents

Practical syntheses of chiral α-amino acids and chiral half-esters by kinetic resolution of urethane-protected α-amino acid N-carboxyanhydrides and desymmetrization of cyclic meso-anhydrides with new modified cinchona alkaloid catalysts

The large-scale applications of the kinetic resolution of urethane-protected α-amino acid N-carboxyanhydrides (UNCAs) and the desymmetrization of cyclic meso-anhydrides using modified cinchona alkaloids are described. These asymmetric reactions are effective organocatalytic methods for the synthesis of chiral a-amino acids 6 and chiral half-esters 2 on an industrial scale, because the organocatalyst recovery and product purification can be carried out by a simple extractive procedure obviating a chromatographic purification step. The modified cinchona alkaloid catalysts (DHQD) 2AQN and (DHQ)2AQN, as reported by Deng and co-workers, are not readily available and therefore not suitable for industrial-scale synthesis. Various O-alkylated quinidine and quinine derivatives were prepared and screened as catalysts for the kinetic resolution of phenylalanine UNCA with alcohol. The readily prepared O-propargylquinidine (OPQD) and O-propargylquinine (OPQ) were discovered to be highly enantioselective and practical catalysts. These new catalysts were applied to the synthesis of chiral propargylglycine 24 and the key intermediate of BAY10-8888/PLD-118, 26, on an industrial scale, by the kinetic resolution of UNCA 22 and the desymmetrization of cyclic meso-anhydride 25, respectively.

Novel antifungal β-amino acids: Synthesis and activity against Candida albicans

A series of novel β-amino acids has been synthesized and tested for their in vitro antifungal activity against Candida albicans. A steep SAR was observed. β-Amino acid 21 (BAY 10-8888/PLD-118) revealed the most favourable activity-tolerability profile and was selected for clinical studies as a novel antifungal for the oral treatment of yeast infections.