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

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

Uses

Used in Pharmaceutical Research and Development:
Carbamic acid, (2-fluorocyclopropyl)-, 1,1-dimethylethyl ester, (1R-cis)(9CI) is used as a research compound for its potential pharmacological properties. Its unique structure and stereochemistry make it a valuable tool in drug design and discovery, allowing researchers to investigate its interactions with biological targets and evaluate its therapeutic potential.
Used in Drug Design and Discovery:
In the field of drug design and discovery, Carbamic acid, (2-fluorocyclopropyl)-, 1,1-dimethylethyl ester, (1R-cis)(9CI) is utilized as a starting point for the development of new pharmaceutical agents. Its specific stereochemistry and functional groups can be modified or optimized to enhance its biological activity, selectivity, and pharmacokinetic properties, leading to the creation of novel therapeutic agents with improved efficacy and safety profiles.
Used in Stereochemistry Studies:
The 1R-cis configuration of Carbamic acid, (2-fluorocyclopropyl)-, 1,1-dimethylethyl ester, (1R-cis)(9CI) makes it an interesting subject for stereochemistry studies. Researchers can investigate the impact of stereochemistry on the compound's biological activity, selectivity, and pharmacokinetics, providing valuable insights into the role of stereochemistry in drug action and development.
Used in Chemical Synthesis:
Carbamic acid, (2-fluorocyclopropyl)-, 1,1-dimethylethyl ester, (1R-cis)(9CI) can also be used as a building block or intermediate in the synthesis of more complex organic compounds. Its unique functional groups and stereochemistry can be exploited in various synthetic routes, enabling the preparation of novel compounds with potential applications in various fields, including pharmaceuticals, materials science, and agrochemicals.

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

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

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.

Stereoselective synthesis of cis -2-fluorocyclopropanecarboxylic acid

A rhodium-catalyzed cyclopropanation of 1-fluoro-1-(phenylsulfonyl)ethylene and diazo esters is described as an effective method for the stereoselective synthesis of cis-2-fluorocyclopropanecarboxylic acid. This process provides an example of the cyclopro

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.

Synthetic Studies on the Key Component of the New Generation of Quinolonecarboxylic Acid, DU-6859. 2. Asymmetric Synthesis of (1R,2S)-2-Fluorocyclopropylamine

The title synthesis was achieved by featuring diastereoface-selective cyclopropanation of (4R,5S)-4,5-diphenyl-3-vinyl-2-oxazolidinone and its related compounds, the chiral conformationally rigid N-vinylcarbamates, with zinc-monofluorocarbenoid, followed

Fluorocyclopropyl quinolones. 1. Synthesis and structure-activity relationships of 1-(2-fluorocyclopropyl)-3-pyridonecarboxylic acid antibacterial agents

A series of 1-(2-fluorocyclopropyl)-3-pyridonecarboxylic acids has been prepared. These derivatives are characterized by having a fluorine atom at the 2-position on the cyclopropane ring as the N1 substituent and consist of both cis and trans stereoisomers. Structure-activity relationship studies indicate that the cis derivatives are more potent against Gram-positive bacteria than the corresponding trans counterparts, but the difference in potency against most Gram-negative bacteria is much smaller. The inhibitory effect of compounds 4, 5, 26, 27, 38, and 39 on supercoiling activity of DNA gyrase obtained from E. coli KL-16 correlated with their MICs against the same strain and also depend on their (26, 27, 38, 39) stereochemistry. Introduction of a fluorine atom on the cyclopropyl group resulted in the reduction of lipophilicity compared with the corresponding nonfluorinated quinolones.

Synthesis and optical resolution of dl-cis-2-fluorocyclopropylamine, the key component of the new generation of quinolonecarboxylic acid, DU-6859

The title synthesis was accomplished by featuring highly cis-selective cyclopropanation of an N-vinylcarbamate with zinc-monofluorocarbenoid followed by deprotection of the formed N-(cis-2-fluorocyclopropyl)carbamate. Optical resolution of dl-cis-2-fluoro

Asymmetric Synthesis of (1R,2S)-2-Fluorocyclopropylamine, the Key Intermediate of the New Generation of Quinolonecarboxylic Acid, DU-6859

The title synthesis was achieved by featuring diastereoface selective cyclopropanation of (4R,5S)-4,5-diphenyl-3-vinyl-2-oxazolidinone, the chiral and conformationally rigid N-vinylcarbamate, with zincmonofluorocarbenoid followed by hydrogenolysis of form