23761-23-1

Basic information

• Product Name: 3-Oxocyclobutanecarboxylic acid
• Synonyms: 3-OXO-CYCLOBUTANECARBOXYLIC ACID;(3-oxocyclobutyl)carboxylic acid;IFLAB-BB F2124-0041;CYCLOBUTANECARBOXYLIC ACID, 3-OXO-;3-Oxocyclobutanecarboxylic;3-Oxycyclobutanecarboxylic acid;3-Oxo-cyclobutanecarboxylic acid ,95%;3-Oxocyclobutanecarboxyli...
• CAS NO: 23761-23-1
• Molecular Formula: C5H6O3
• Molecular Weight: 114.1
• Product Categories: API intermediates;Pharmaceutical intermediate;Miscellaneous Reagents;Building Blocks/Intermediates
• Mol File: 23761-23-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: 69-70℃
• Boiling Point: 296°C
• Flash Point: 147°C
• Appearance: Off-white/Solid
• Density: 1.431
• Vapor Pressure: 0.000345mmHg at 25°C
• Refractive Index: 1.531
• Storage Temp.: Room temperature.
• PKA: 4.35±0.20(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 3-Oxocyclobutanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Oxocyclobutanecarboxylic acid(23761-23-1)
• EPA Substance Registry System: 3-Oxocyclobutanecarboxylic acid(23761-23-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 26-37-60
• TSCA: No
• Hazardous Substances Data: 23761-23-1(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

3-Oxocyclobutanecarboxylic Acid (cas# 23761-23-1) is a compound useful in organic synthesis.

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 3841, 1988 DOI: 10.1021/jo00251a033

InChI:InChI=1/C5H6O3/c6-4-1-3(2-4)5(7)8/h3H,1-2H2,(H,7,8)

Synthetic route

3,3-dimethoxycyclobutane-1,1-dicarboxylic acid diisopropyl ester (115118-68-8) → 3-oxocyclobutanecarboxylic acid (23761-23-1)

Conditions	Yield
With hydrogenchloride In water for 10h; Reflux;	98%
With hydrogenchloride for 60h; Heating;	97%
With hydrogenchloride; water for 60h; Heating / reflux;	96.8%

diethyl 3,3-dimethoxycyclobutane-1,1-dicarboxylate (115118-67-7) → 3-oxocyclobutanecarboxylic acid (23761-23-1)

Conditions	Yield
With hydrogenchloride; water for 50h; Heating / reflux;	70%

3-methylenecyclobutane-1-carboxylic acid (15760-36-8) → 3-oxocyclobutanecarboxylic acid (23761-23-1)

Conditions	Yield
With sodium periodate; osmium(VIII) oxide
With potassium osmate(VI) dihydrate; sodium periodate In tetrahydrofuran; water at 28℃; Industry scale;

3-methylenecyclobutanecarbonitrile (15760-35-7) → 3-oxocyclobutanecarboxylic acid (23761-23-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; potassium hydroxide / ethanol / 2 h / Reflux 2: potassium osmate(VI) dihydrate; sodium periodate / tetrahydrofuran; water / 28 °C / Industry scale View Scheme

Upstream product

• 15760-36-8 3-methylenecyclobutane-1-carboxylic acid 
• 15760-35-7 3-methylenecyclobutanecarbonitrile 
• 115118-67-7 diethyl 3,3-dimethoxycyclobutane-1,1-dicarboxylate 
• 115118-68-8 3,3-dimethoxycyclobutane-1,1-dicarboxylic acid diisopropyl ester 

Downstream Products

• 98431-64-2 N,N-dimethyl-3-oxocyclobutane-1-carboxamide 
• 1186202-25-4 2,4-dioxo-1,3-diazaspiro[3.4]octane-2-carboxylic acid 
• 73550-55-7 Cis-ACBD 
• 117488-23-0 1-aminocyclobutane-cis-1,3-dicarboxylic acid 
• 145549-76-4 tert-butyl 3-oxocyclobutane-1-carboxylate 
• 98231-07-3 3,3-dimethoxycyclobutanecarboxylic acid methyl ester 
• 198995-91-4 benzyl 3-oxocyclobutane-1-carboxylate 
• 917827-89-5 N-benzyl-3-oxocyclobutanecarboxamide 
• 1186047-07-3 3-hydroxy-3-(3-methoxyphenyl)cyclobutane-1-carboxylic acid 
• 1374134-33-4 methyl 3-(2-fluoro-4-methoxyphenyl)-3-hydroxycyclobutanecarboxylate 
• 1245647-19-1 3-(((tert-butyldimethylsilyl)oxy)methyl)cyclobutan-1-ol 
• 112623-19-5 3-(hydroxymethyl)cyclobutanol 
• 939775-62-9 3-((tert-butyldimethylsilyl)oxy)methylcyclobutan-1-one 
• 1234616-26-2 3-(3,3-difluorocyclobutyl)-3-oxopropanenitrile 

Relevant articles and documents

Preparation method 3 - oxocyclobutane-based carboxylic acid

The invention discloses a preparation method of 3 -oxocyclobutane-based carboxylic acid, and belongs to the technical field of synthesis of medical intermediates. The ketone is protected from 1, 3 -dihydroxyacetone by condensation with trimethyl orthoformate to give 2, 2 -dimethoxy -1, 3 -propanediol, followed by reaction with malonate to give 3, 3 -dimethylcyclobutyl -1, 1 -dicarboxylic acid diester, followed by hydrolysis under acidic conditions. Decarboxylation and deprotection to yield 3 -oxocyclobutane-based carboxylic acids. The method has the advantages of high yield, common and easily available raw materials, simple flow and industrial amplification prospect.

Preparation method of 3-oxocyclobutylcarboxylic acid

The invention belongs to the technical field of organic synthesis, and specifically relates to a preparation method of 3-oxocyclobutylcarboxylic acid. According to the preparation method, 3,3-dimethoxylcyclobutyl-1,1-diisopropyl dicarboxylate, methanol, and sodium hydroxide are taken as the raw materials, and raw materials react with hydrochloric acid to prepare 3-oxocyclobutylcarboxylic acid. Thereactions are quick, the method is simple, the technology is safe, the raw materials are easily available and cheap, the yield of the two-step reactions can reach 80% or more, and the production purity and yield are effectively increased.

ANTIBACTERIAL AGENTS

Antibacterial compounds of formula (I) are provided, as well as stereoisomers and pharmaceutically acceptable salts and esters thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of such compounds.