163457-22-5

Basic information

• Product Name: 1-CBZ-3,3-DIFLUOROPYRROLIDINE
• Synonyms: 1-CBZ-3,3-DIFLUOROPYRROLIDINE;Benzyl 3,3-difluoropyrrolidine-1-carboxylate
• CAS NO: 163457-22-5
• Molecular Formula: C₁₂H₁₃F₂NO₂
• Molecular Weight: 241.23
• Product Categories: pharmacetical
• Mol File: 163457-22-5.mol

Chemical Properties

• Boiling Point: 321°C at 760 mmHg
• Flash Point: 147.9°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 0.000307mmHg at 25°C
• Refractive Index: 1.526
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-CBZ-3,3-DIFLUOROPYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CBZ-3,3-DIFLUOROPYRROLIDINE(163457-22-5)
• EPA Substance Registry System: 1-CBZ-3,3-DIFLUOROPYRROLIDINE(163457-22-5)

Safety Data

• Hazardous Substances Data: 163457-22-5(Hazardous Substances Data)

Usage

Chemical Family

Belongs to the pyrrolidine family

Versatility

Acts as a versatile building block in organic synthesis

Industry Applications

Widely used in pharmaceutical and agrochemical industries

Reactivity

Known for its unique reactivity

Intermediate Role

Commonly used as a key intermediate in the synthesis of various biologically active compounds

Substituents

Contains 3,3-difluoro substituents

Medicinal Chemistry

Valuable tool in medicinal chemistry

Enhancement

Enhances the biological activity and pharmacokinetic properties of the final compounds

Field Importance

Important compound in drug discovery and development

InChI:InChI=1/C12H13F2NO2/c13-12(14)6-7-15(9-12)11(16)17-8-10-4-2-1-3-5-10/h1-5H,6-9H2

Upstream product

• 501-53-1 benzyl chloroformate 
• 130312-02-6 benzyl 3-oxopyrrolidine-1-carboxylate 
• 100858-33-1 (3R)-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester 

Downstream Products

• 316131-01-8 3,3-difluoropyrrolidine 

Relevant articles and documents

Aminodifluorosulfinium salts: Selective fluorination reagents with enhanced thermal stability and ease of handling

Diethylaminodifluorosulfinium tetrafluoroborate (XtalFluor-E) and morpholinodifluorosulfinium tetrafluoroborate (XtalFluor-M) are crystalline fluorinating agents that are more easily handled and significantly more stable than Deoxo-Fluor, DAST, and their analogues. These reagents can be prepared in a safer and more cost-efficient manner by avoiding the laborious and hazardous distillation of dialkylaminosulfur trifluorides. Unlike DAST, Deoxo-Fluor, and Fluolead, XtalFluor reagents do not generate highly corrosive free-HF and therefore can be used in standard borosilicate vessels. When used in conjunction with promoters such as Et3N3HF, Et3N2HF, or DBU, XtalFluor reagents effectively convert alcohols to alkyl fluorides and carbonyls to gem-difluorides. These reagents are typically more selective than DAST and Deoxo-Fluor and exhibit superior performance by providing significantly less elimination side products.

Aminodifluorosulfinium Tetrafluoroborate salts as stable and crystalline deoxofluorinating reagents

Aminodifluorosulfinium tetrafluoroborate salts were found to act as efficient deoxofluorinating reagents when promoted by an exogenous fluoride source and, In most cases, exhibited greater selectivity by providing less elimination byproduct as compared to DAST and DeoxoFluor. Aminodifluorosulfinium tetrafluoroborates are easy handled crystalline salts that show enhanced thermal stability over dialkylaminosulfur trifluorides, are storage-stable, and unlike DAST and Deoxo-Fluor do not react violently with water.

HETEROCYCLIC CETP INHIBITORS

Compounds of formula Ia and Ib wherein A, B, C and R1 are described herein.

CYCLOHEXYLALANINE DERIVATIVES AS DIPEPTIDYL PEPTIDASE-IV INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES

The present invention is directed to novel cyclohexylalanine derivatives which are inhibitors of the dipeptidyl peptidase-IV enzyme ("DP-IV inhibitors") and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

1,2,4-OXADIAZOLE DERIVATIVES AS DIPEPTIDYL PEPTIDASE-IV INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES

The present invention is directed to novel 1,2,4-oxadiazole derivatives which are inhibitors of the dipeptidyl peptidase-IV enzyme ("DP-IV inhibitors") and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

FUSED PHENYLALANINE DERIVATIVES AS DIPEPTIDYL PEPTIDASE-IV INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES

The present invention is directed to fused phenylalanine derivatives which are inhibitors of the dipeptidyl peptidase-IV enzyme ("DP-IV inhibitors") and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

FUSED BENZENE DERIVATIVE AND USE

The present invention provides a compound represented by the general formula: [wherein Ring A represents an optionally substituted 5- to 8-membered ring, Ring B represents a further optionally substituted 4- to 10-membered ring, Ring C represents a further optionally substituted benzene ring, X1 represents carbon atom, X2 represents a carbon atom, an oxygen atom, etc., W represents a nitrogen atom, etc., Y11 represents a group represented by the formula CR2R3' (wherein R2 represents a hydrogen atom, a cyano group, a nitro group, etc., and R3' represents a hydrogen atom, a cyano group, a nitro group, etc., respectively), Y21 represents a group represented by the formula CR4R5' (wherein R4 represents a hydrogen atom, a cyano group, a nitro group, etc., and R5' represents a hydrogen atom, a cyano group, a nitro group, etc., respectively), etc., and R1 represents an electron-withdrawing group, respectively. The formula represents a single bond or a double bond] or a salt thereof, which is useful as an androgen receptor modulator.

PHENYLALANINE DERIVATIVES AS DIPEPTIDYL PEPTIDASE INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES

The present invention is directed to phenylalanine derivatives which are inhibitors of the dipeptidyl peptidase-IV enzyme ("DP-IV inhibitors") and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

Fluoropyrrolidine amides as dipeptidyl peptidase IV inhibitors

Amides derived from fluorinated pyrrolidines and 4-substituted cyclohexylglycine analogues have been prepared and evaluated as inhibitors of dipeptidyl dipeptidase IV (DP-IV). Analogues which incorporated (S)-3-fluoropyrrolidine showed good selectivity for DP-IV over quiescent cell proline dipeptidase (QPP). Compound 48 had good pharmacokinetic properties and was orally active in an oral glucose tolerance test in lean mice.