127199-16-0

Basic information

• Product Name: Carbamic acid, (2-fluorocyclopropyl)-, 1,1-dimethylethyl ester, (1R-cis)- (9CI)
• Synonyms: Carbamic acid, (2-fluorocyclopropyl)-, 1,1-dimethylethyl ester, (1R-cis)- (9CI);(1R-cis)-(2-Fluorocyclopropyl)carbamic acid tert-butyl ester;tert-butyl ((1R,2S)-2-fluorocyclopropyl)carbamate(WX191572);Carbamic acid,N-[(1R,2S)-2-fluorocyclopropyl]-, 1,1-dimethylethyl ester
• CAS NO: 127199-16-0
• Molecular Formula: C₈H₁₄FNO₂
• Molecular Weight: 175.2006632
• Product Categories: N-BOC
• Mol File: 127199-16-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 238.4 °C at 760 mmHg
• Flash Point: 98 °C
• Appearance: White to off-white powder
• Density: 1.09 g/cm³
• Vapor Pressure: 0.0426mmHg at 25°C
• Refractive Index: 1.444
• PKA: 11.37±0.40(Predicted)
• CAS DataBase Reference: Carbamic acid, (2-fluorocyclopropyl)-, 1,1-dimethylethyl ester, (1R-cis)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (2-fluorocyclopropyl)-, 1,1-dimethylethyl ester, (1R-cis)- (9CI)(127199-16-0)
• EPA Substance Registry System: Carbamic acid, (2-fluorocyclopropyl)-, 1,1-dimethylethyl ester, (1R-cis)- (9CI)(127199-16-0)

Safety Data

• Hazardous Substances Data: 127199-16-0(Hazardous Substances Data)

Usage

General Description

Carbamic acid, (2-fluorocyclopropyl)-, 1,1-dimethylethyl ester, (1R-cis)- (9CI) is a chemical compound that is commonly used in pharmaceutical research and development. It is an ester of carbamic acid, containing a 2-fluorocyclopropyl group and a 1,1-dimethylethyl group. Carbamic acid, (2-fluorocyclopropyl)-, 1,1-dimethylethyl ester, (1R-cis)- (9CI) is typically synthesized for its potential pharmacological properties and is of interest in the study of drug design and discovery. Its 1R-cis configuration indicates a specific stereochemistry that can influence its biological activity. Further research is ongoing to explore the potential applications and effects of this compound in various fields.

InChI:InChI=1/C8H14FNO2/c1-8(2,3)12-7(11)10-6-4-5(6)9/h5-6H,4H2,1-3H3,(H,10,11)/t5-,6+/m0/s1

Upstream product

• 1493-01-2 fluorodiiodomethane 
• 7150-72-3 t-butyl N-vinylcarbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 141042-21-9 (-)-cis-2-fluorocyclopropylamine hydrochloride 
• 114152-95-3 (1R*,2R*)-2-fluorocyclopropylamine hydrochloride 
• 114152-95-3 (1R*,2S*)-2-fluorocyclopropylamine hydrochloride 
• 127199-14-8 (1S,2S)-2-fluorocyclopropane-1-carboxylic acid 
• 75-65-0 tert-butyl alcohol 
• 156816-78-3 2-fluorocyclopropane-carboxylic acid 

Downstream Products

• 143062-84-4 (1R,2S)-2-fluorocyclopropylamine p-toluenesulfonic acid salt 

Relevant articles and documents

Novel process for synthesizing 2 -fluorocyclopropylamine with high selectivity and asymmetric synthesis

A novel highly selective asymmetric synthesis process of 2 -fluorocyclopropylamine (Structural I). The method provided by the invention uses 1 - fluorine -1 - benzene (propylene) sulfonyl methane and chiral epichlorohydrin to construct chiral cyclopropane under basic conditions, and a new synthetic route not only achieves a special cis-trans selectivity, but also has a highly specific stereoselectivity. The synthesis route is efficient, the reaction condition is mild, the method is suitable for large industrial production in a green environment, 2 -fluorocyclopropylamine production cost is greatly reduced.

Synthetic studies on the key component of the new generation of quinolonecarboxylic acid, DU-6859. 1. Synthesis of (1R,2S)-2-fluorocyclopropylamine by the use of optical resolution

The title synthesis was achieved by employing highly cis-selective cyclopropanation of N-benzyl-N-vinylcarbamates with zinc-monofluorocarbenoid, deprotection of the formed N-benzyl-N-(cis-2-fluorocyclopropyl)carbamates, and optical resolution of the resul

(Fluorocyclopropyl)quinolones. 2. Synthesis and stereochemical structure- activity relationships of chiral 7-(7-amino-5-azaspiro[2.4]heptan-5-yl)-1- (2-fluorocyclopropyl)quinolone antibacterial agents

A series of novel chiral 7-(7-amino-5-azaspiro[2.4]heptan-5-yl)-8-chloro- 1-(2-fluorocyclopropyl)-quinolones were synthesized as a continuation of a research project of 1-(2-fluorocyclopropyl)-quinolones by considering stereochemical and physicochemical properties of the molecule. Absolute configurations of the 1-(cis-2-fluorocyclopropyl) moiety and the 7-(7-amino- 5-azaspiro-[2.4]heptan-5-yl) moiety were determined by X-ray crystallographic analysis. Stereochemical structure-activity relationship studies indicated that 1-[(1R,2S)-2-fluorocyclopropyl] and 7-[(7S)-amino-5-azaspiro[2.4]heptan- 5-yl] derivatives are more potent against Gram-positive and Gram-negative bacteria than the other stereoisomers and 7-[(7S)-7-amino-5-azaspiro[2.4]- heptan-5-yl]-8-chloro-1-[(1R,2S)-2-fluorocyclopropyl]quinolone (33) is the most potent of all stereoisomers. Pharmacokinetic profiles and physicochemical properties of the selected compounds were also examined, and it was found that 33 (DU-6859a) possesses moderate lipophilicity and good pharmacokinetic profiles.