107259-06-3

Basic information

• Product Name: TERT-BUTYL (1-FORMYLCYCLOPROPYL)CARBAMATE
• Synonyms: TERT-BUTYL (1-FORMYLCYCLOPROPYL)CARBAMATE;(1-Formyl-cyclopropyl)-carbamic acid tert-butyl ester;1-((pivaloyloxy)amino)cyclopropanecarbaldehyde;1-(tert-Butoxycarbonylamino)cyclopropanecarboxaldehyde;1-(tert-Butoxycarbonylamino)cyclopropanecarboxaldehyde (1-Formylcyclopropyl)carbamic acid tert-butyl ester;Carbamic acid, N-(1-formylcyclopropyl)-, 1,1-dimethylethyl ester;tert-Butyl(l -formylcyclopropyl)carbamate
• CAS NO: 107259-06-3
• Molecular Formula: C₉H₁₅NO₃
• Molecular Weight: 185.22
• Mol File: 107259-06-3.mol
• Article Data: 29

Chemical Properties

• Melting Point: 76.5-78.50℃
• Boiling Point: 280.708 °C at 760 mmHg
• Flash Point: 123.568 °C
• Appearance: /
• Density: 1.102 g/cm³
• PKA: 10.88±0.20(Predicted)
• CAS DataBase Reference: TERT-BUTYL (1-FORMYLCYCLOPROPYL)CARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL (1-FORMYLCYCLOPROPYL)CARBAMATE(107259-06-3)
• EPA Substance Registry System: TERT-BUTYL (1-FORMYLCYCLOPROPYL)CARBAMATE(107259-06-3)

Safety Data

• Hazardous Substances Data: 107259-06-3(Hazardous Substances Data)

Usage

General Description

Tert-butyl (1-formylcyclopropyl)carbamate is a chemical compound that is used in organic synthesis as a reagent for the preparation of various pharmaceuticals and agrochemicals. It is a carbamate derivative of tert-butyl and cyclopropyl, and is commonly used as a protecting group for amines in organic chemistry. tert-Butyl (1-formylcyclopropyl)carbamate is known for its stability and compatibility with a wide range of reaction conditions, making it a versatile tool in the synthesis of complex organic molecules. Additionally, it has also been studied for its potential as a herbicidal and insecticidal agent.

Upstream product

• 88950-64-5 1-<(tert-butyloxy)carbonylamino>cyclopropane-1-carboxylic acid 
• 161521-10-4 1-<(t-butoxycarbonyl)amino>cyclopropane-1-carbonyl-N,O-dimethylhydroxylamide 
• 107259-05-2 1-tert-butoxycarbonylamino-cyclopropanecarboxylic Acid Ethyl Ester 
• 107017-73-2 tert-butyl (1-(hydroxymethyl)cyclopropyl)carbamate 

Downstream Products

• 1027338-34-6 tert-butyl N-[1-(aminomethyl)cyclopropyl]carbamate 
• 1268810-09-8 tert-butyl N-(1-ethynylcyclopropyl)carbamate 
• 1414358-09-0 tert-butyl N-[1-[3-[(2R)-2-[[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidin-1-yl]-2-cyano-3-oxo-prop-1-enyl]cyclopropyl]carbamate 

Relevant articles and documents

The Alkyne Moiety as a Latent Electrophile in Irreversible Covalent Small Molecule Inhibitors of Cathepsin K

Irreversible covalent inhibitors can have a beneficial pharmacokinetic/pharmacodynamics profile but are still often avoided due to the risk of indiscriminate covalent reactivity and the resulting adverse effects. To overcome this potential liability, we introduced an alkyne moiety as a latent electrophile into small molecule inhibitors of cathepsin K (CatK). Alkyne-based inhibitors do not show indiscriminate thiol reactivity but potently inhibit CatK protease activity by formation of an irreversible covalent bond with the catalytic cysteine residue, confirmed by crystal structure analysis. The rate of covalent bond formation (kinact) does not correlate with electrophilicity of the alkyne moiety, indicative of a proximity-driven reactivity. Inhibition of CatK-mediated bone resorption is validated in human osteoclasts. Together, this work illustrates the potential of alkynes as latent electrophiles in small molecule inhibitors, enabling the development of irreversible covalent inhibitors with an improved safety profile.

CATHEPSIN INHIBITORS

This invention relates to compounds that are useful as inhibitors, in particular as inhibitors of Cathepsin K (CatK), and to a method of inhibiting cathepsin activity, comprising administering a compound or formulation comprising a compound according to the invention.

ANTIBACTERIAL ANNULATED PYRROLIDIN-2-ONE DERIVATIVES

The invention relates to antibacterial compounds of formula I wherein X represents sulphur or CH=CH; R1 represents H, PO3H2, SO3H, phosphonooxymethyl or the group -CO-R2 wherein R2 is as defined in the claims M is one of the groups MA and MB represented below wherein A represents a bond or C≡C and R1A, R2A, R3A and R1B are as defined in the claims; and to salts thereof.