154748-49-9

Basic information

• Product Name: Carbamic acid, (3-oxocyclobutyl)-, 1,1-dimethylethyl ester (9CI)
• Synonyms: Carbamic acid, (3-oxocyclobutyl)-, 1,1-dimethylethyl ester (9CI);3-OXOCYCLOBUTYLCARBAMIC ACID, 1,1-DIMETHYLETHYL ESTER;3-(tert-Butyloxycarbonylamino)cyclobutan-1-one;(3-Oxo-cyclobutyl)-carbamic acid tert-butyl ester;Tert-butyl3-oxocyclobutylcarbamate;tert-butyl 3-oxocyclobuty...;CarbaMic acid, N-(3-oxocyclobutyl)-, 1,1-diMethylethyl ester;3-(Boc-amino)cyclobutanone
• CAS NO: 154748-49-9
• Molecular Formula: C9H15NO3
• Molecular Weight: 185.2203
• EINECS: 2017-001-1
• Product Categories: N-BOC;Amines;Building Blocks;C8 to C9;C9;Chemical Synthesis;Ethers;New Products for Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Oxygen Compounds
• Mol File: 154748-49-9.mol

Chemical Properties

• Melting Point: 120-125℃
• Boiling Point: 302.1 °C at 760 mmHg
• Flash Point: 136.5 °C
• Appearance: /
• Density: 1.1 g/cm³
• Vapor Pressure: 0.00101mmHg at 25°C
• Refractive Index: 1.474
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 11.60±0.20(Predicted)
• CAS DataBase Reference: Carbamic acid, (3-oxocyclobutyl)-, 1,1-dimethylethyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (3-oxocyclobutyl)-, 1,1-dimethylethyl ester (9CI)(154748-49-9)
• EPA Substance Registry System: Carbamic acid, (3-oxocyclobutyl)-, 1,1-dimethylethyl ester (9CI)(154748-49-9)

Safety Data

• Statements: 52-51/53-36/37/38
• Safety Statements: 3/9-4-22-26-28-29-35-44
• RIDADR: 3077
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 154748-49-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Carbamic acid, (3-oxocyclobutyl)-, 1,1-dimethylethyl ester (9CI) is used as a synthetic intermediate for the preparation of 5-HT1-like receptor agonists. These agonists are important in the development of medications targeting various central nervous system disorders, such as migraine, anxiety, and depression.
Used in Antiviral Drug Synthesis:
In the field of antiviral drug development, Carbamic acid, (3-oxocyclobutyl)-, 1,1-dimethylethyl ester (9CI) is utilized to synthesize (oxadiazolyl)quinoline derivatives. These derivatives have been identified as highly potent inhibitors of the Hepatitis C Virus (HCV) NS4B protein, which plays a crucial role in the viral replication process. By targeting this protein, these inhibitors can potentially help in the development of effective treatments for HCV infections.
Used in Chemical Synthesis:
Carbamic acid, (3-oxocyclobutyl)-, 1,1-dimethylethyl ester (9CI) can also be employed as a versatile building block in the synthesis of various organic compounds. Its unique structural features and reactivity make it a valuable component in the development of new molecules with potential applications in various industries, such as agrochemicals, materials science, and specialty chemicals.

Form

Solid

InChI:InChI=1/C9H15NO3/c1-9(2,3)13-8(12)10-6-4-7(11)5-6/h6H,4-5H2,1-3H3,(H,10,12)

Upstream product

• 130369-04-9 (3-methylene-cyclobutyl)-carbamic acid tert-butyl ester 
• 1035374-20-9 3-aminocyclobutan-1-one hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 75-65-0 tert-butyl alcohol 
• 23761-23-1 3-oxocyclobutanecarboxylic acid 
• 130233-77-1 3-oxocyclobutane-1-carbonyl chloride 
• 4640-43-1 N-3-aminocyclobutan-1-one 
• 7150-72-3 t-butyl N-vinylcarbamate 

Downstream Products

• 389890-43-1 tert-butyl (1,3-cis)-N-(3-hydroxycyclobutyl)carbamate 
• 1029720-19-1 tert-butyl (3,3-difluorocyclobutyl)carbamate 
• 1355328-30-1 N-(3,3-difluorocyclobutyl)formamide 
• 1448348-04-6 (4S)-N-(1-(2-Chlorophenyl)-2-(3,3-difluorocyclobutylamino)-2-oxoethyl)-N-(3-fluoro-phenyl)-2-oxooxazolidine-4-carboxamide 
• 1448345-75-2 (S)-N-((R)-1-(2-chlorophenyl)-2-(3,3-difluorocyclobutylamino)-2-oxoethyl)-N-(3-fluorophenyl)-2-oxo-3-(pyrimidin-2-yl)oxazolidine-4-carboxamide 
• 1448348-05-7 (S)-N-(1-(2-Chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-N-(3-fluoro-phenyl)-6-oxopiperidine-2-carboxamide 
• 1448348-25-1 (S)-N-((S)-1-( 2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-N-(3-fluorophenyl)-5-oxomorpholine-3-carboxamide 
• 1448346-14-2 (S)-N-((S)-1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-N-(3-fluorophenyl)-5-oxo-4-(pyrimidin-2-yl)morpholine-3-carboxamide 
• 1448348-39-7 5-((2S)-N-(1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-1-(4-cyano pyridin-2-yl)-5-oxopyrrolidine-2-carboxamido)isophthalamide 
• 1448347-64-5 (2S)-N-(1-(2-Chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-1-(4-cyanopyridin-2-yl)-N-(3,5-dicyanophenyl)-5-oxopyrrolidine-2-carboxamide 
• 1448348-13-7 (2S)-4-(tert-Butyldimethylsilyloxy)-N-(1-(2-chlorophenyl)-2-(3,3-difluorocyclobut-ylamino)-2-oxoethyl)-N-(3-fluorophenyl)-4-methyl-5-oxopyrrolidine-2-carboxamide 
• 1448348-14-8 (2S)-4-(tert-Butyldimethylsilyloxy)-N-(1-(2-chlorophenyl)-2-(3,3-difluorocyclobutyl-amino)-2-oxoethyl)-1-(4-cyanopyridin-2-yl)-N-(3-fluorophenyl)-4-methyl-5-oxopyrrolidine-2-carboxamide 
• 1448348-22-8 (4S)-N-(1-(2-Chlorophenyl)-2-(3,3-difluorocyclobutylamino)-2-oxoethyl)-N-(3-fluoro-phenyl)-1-methyl-2-oxoimidazolidine-4-carboxamide 
• 1448348-21-7 Ethyl 2-((4S)-4-((1-(2-chlorophenyl)-2-(3,3-difluorocyclobutylamino)-2-oxoethyl)(3-fluorophenyl)carbamoyl)-2-oxoimidazolidin-1-yl)acetate 

Relevant articles and documents

Preparation method of tert-butyl 3-oxocyclobutyl carbamate

The invention belongs to the technical field of medicines, and particularly relates to a preparation method of tert-butyl 3-oxocyclobutyl carbamate (I). The method comprises the following steps: protecting a compound IV to generate a compound III, carrying out Hofmann degradation reaction to obtain a compound II, and finally, carrying out deprotection to obtain a compound I. Compared with the prior art, the method is low in technical route cost and mild in reaction condition, avoids the use of toxic reagents with larger danger coefficients, is green and environment-friendly, and has good application value.

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A method for Ni-catalyzed hydroalkylation of internal alkynes with cycloketone oxime esters was developed. The reaction has a broad substrate scope. This hydroalkylation shows excellent regio-and stereo-selectivity. This method enables readily available starting materials to be used to access a range of cyano-substituted single-configuration trisubstituted alkenes. These are valuable feedstock chemicals and are widely used in synthetic and medicinal chemistry.

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