102821-72-7

Basic information

• Product Name: 5-(2-FLUORO-PHENYL)-CYCLOHEXANE-1,3-DIONE
• Synonyms: 5-(2-FLUORO-PHENYL)-CYCLOHEXANE-1,3-DIONE;5-(2-fluorophenyl)-1,3-Cyclohexanedione
• CAS NO: 102821-72-7
• Molecular Formula: C₁₂H₁₁FO₂
• Molecular Weight: 206.21
• Mol File: 102821-72-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 335.6 °C at 760 mmHg
• Flash Point: 128.6 °C
• Appearance: /
• Density: 1.228 g/cm³
• Vapor Pressure: 0.000119mmHg at 25°C
• Refractive Index: 1.536
• CAS DataBase Reference: 5-(2-FLUORO-PHENYL)-CYCLOHEXANE-1,3-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2-FLUORO-PHENYL)-CYCLOHEXANE-1,3-DIONE(102821-72-7)
• EPA Substance Registry System: 5-(2-FLUORO-PHENYL)-CYCLOHEXANE-1,3-DIONE(102821-72-7)

Safety Data

• Hazardous Substances Data: 102821-72-7(Hazardous Substances Data)

Usage

General Description

5-(2-Fluoro-phenyl)-cyclohexane-1,3-dione is an organic compound with the chemical formula C12H11FO2. It is a cyclic diketone with a cyclohexane ring and a fluorophenyl substituent. 5-(2-FLUORO-PHENYL)-CYCLOHEXANE-1,3-DIONE is used in organic synthesis and pharmaceutical research as a building block for the synthesis of various compounds, including potential drug candidates. It has also been studied for its potential biological activity and has shown promise as a potential anti-inflammatory and analgesic agent. Additionally, it has been investigated for its potential use in material science and as a precursor for the synthesis of functionalized cyclohexanone derivatives.

InChI:InChI=1/C12H11FO2/c13-12-4-2-1-3-11(12)8-5-9(14)7-10(15)6-8/h1-4,8H,5-7H2

Upstream product

• 446-52-6 2-Fluorobenzaldehyde 
• 148775-25-1 4-(2-fluorophenyl)but-3-en-2-one 
• 105-53-3 diethyl malonate 

Downstream Products

• 1609374-94-8 5-(2-fluorophenyl)-2-(1-((2-methoxyphenyl)amino)ethylidene)cyclohexane-1,3-dione 
• 1083067-18-8 2-acetyl-5-(2-fluorophenyl)cyclohexane-1,3-dione 
• 239130-85-9 7-(2-fluorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one 

Relevant articles and documents

Cyclohexane 1,3-diones and their inhibition of mutant SOD1-dependent protein aggregation and toxicity in PC12 cells

Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease characterized by the progressive loss of motor neurons. Currently, there is only one FDA-approved treatment for ALS (riluzole), and that drug only extends life, on average, by 2-3 months. Mutations in Cu/Zn superoxide dismutase (SOD1) are found in familial forms of the disease and have played an important role in the study of ALS pathophysiology. On the basis of their activity in a PC12-G93A-YFP high-throughput screening assay, several bioactive compounds have been identified and classified as cyclohexane-1,3-dione (CHD) derivatives. A concise and efficient synthetic route has been developed to provide diverse CHD analogs. The structural modification of the CHD scaffold led to the discovery of a more potent analog (26) with an EC50 of 700 nM having good pharmacokinetic properties, such as high solubility, low human and mouse metabolic potential, and relatively good plasma stability. It was also found to efficiently penetrate the blood-brain barrier. However, compound 26 did not exhibit any significant life span extension in the ALS mouse model. It was found that, although 26 was active in PC12 cells, it had poor activity in other cell types, including primary cortical neurons, indicating that it can penetrate into the brain, but is not active in neuronal cells, potentially due to poor selective cell penetration. Further structural modification of the CHD scaffold was aimed at improving global cell activity as well as maintaining potency. Two new analogs (71 and 73) were synthesized, which had significantly enhanced cortical neuronal cell permeability, as well as similar potency to that of 26 in the PC12-G93A assay. These CHD analogs are being investigated further as novel therapeutic candidates for ALS.

PROCESS FOR THE PRODUCTION OF OPTICALLY ACTIVE CYCLIC ENAMINONE DERIVATIVES

A process for the production of optically active cyclic enaminone derivatives characterized by aminating one of the carbonyl groups of a cyclic 1,3-diketone derivative having a symmetry plane to obtain an optically isomeric mixture of chiral cyclic enamin