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

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

Uses

Used in Organic Synthesis:
3-Oxocyclobutanecarboxylic acid is used as a synthetic building block for the production of various organic compounds. Its unique structure and reactivity make it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Oxocyclobutanecarboxylic acid is used as a key intermediate in the development of new drugs. Its incorporation into drug molecules can enhance their efficacy, selectivity, and pharmacokinetic properties, leading to improved therapeutic outcomes.
Used in Agrochemical Industry:
3-Oxocyclobutanecarboxylic acid is also employed in the agrochemical industry for the synthesis of novel pesticides and other crop protection agents. Its use in this sector can contribute to the development of more effective and environmentally friendly products.
Used in Specialty Chemicals:
3-Oxocyclobutanecarboxylic acid finds application in the production of specialty chemicals, such as additives, coatings, and polymers. Its versatility in organic synthesis allows for the creation of innovative materials with unique properties and applications.

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

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 
• 87121-89-9 ethyl 3-oxocyclobutanecarboxylate 
• 100535-42-0 3-dimethylaminomethyl-cyclobutanon-diethylacetal 
• 100050-26-8 3,3-diethoxy-cyclobutanecarboxylic acid dimethylamide 
• 198995-91-4 benzyl 3-oxocyclobutane-1-carboxylate 
• 850643-25-3 3-Oxo-cyclobutanecarboxylic Acid [(3-benzyloxy-phenyl)-(3-chloro-pyrazin-2-yl)-methyl]-amide 
• 766513-34-2 C₁₄H₁₁F₆NO₂ 
• 183616-18-4 3-(hydroxymethyl)-cyclobutan-1-one 
• 917827-84-0 N-benzyl-N-methyl-3-oxocyclobutanecarboxamide 

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-(benzyloxy)-1-cyclobutanone

The invention relates to the technical field of organic synthesis, and specifically relates to synthesis of a medical intermediate 3-(benzyloxy)-1-cyclobutanone, according to the invention, 3-dibromo-2,3-dibromo-2,3,3-tetramethylpiperidine and diisopropyl malonate are used as initial raw materials; firstly, cyclobutane (I) is obtained through a nucleophilic substitution reaction; deprotection andhydrolysis are carried out on a compound (I) under the action of an acid to obtain 3-oxocyclobutanecarboxylic acid (II), the compound (II) is converted into a carboxylic acid silver salt, a Hunsdiecker reaction is carried out on the carboxylic acid silver salt and elemental bromine to obtain alkyl bromide (III), and a nucleophilic substitution reaction is performed on the compound (III) and benzylalcohol to obtain 3-(benzyloxy)-1-cyclobutanone (IV). The method provides a simple industrial production route for 3-(benzyloxy)-1-cyclobutanone, and has the advantages of simple reaction operation,mild reaction conditions and low cost.

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.

Preparation method of 3-oxo-cyclobutanecarboxylic acid

The invention relates to a preparation method of 3-oxo-cyclobutanecarboxylic acid. The preparation method comprises the following steps: enabling 3,3-dimethoxy cyclobutane-1,1-diisopropyl dicarboxylate to react for 4h in a certain concentration of strong alkaline solution at the room temperature; then, adding a certain volume of concentrated hydrochloric acid, continuously carrying out a reflux reaction for 24-48h, and finishing the reaction; cooling the product to the room temperature, extracting by using ethyl acetate, carrying out spin drying, and carrying out recrystallization on the obtained crude product to obtain the pure product. The preparation method is easier in reaction raw material obtaining and rapid in reaction; ethyl ether is not used in the aftertreatment, so that the operation is safe; furthermore, the product is good in yield and high in purity.

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.

CYCLIC AMINE SUBSTITUTED OXAZOLIDINONE CETP INHIBITOR

CCompounds having the structure of Formula I, including pharmaceutically acceptable salts of the compounds, are CETP inhibitors and are useful for raising HDL-cholesterol, reducing LDL-cholesterol, and for treating or preventing atherosclerosis. In the compound of Formula I, A3 is a substitiuted phenyl group or indanyl group.Formula (I)

Elucidating the Origin of diastereoselectivity in a self-replicating system: Selfishness versus altruism

We have investigated a diastereoselective self-replicating system based on a cycloaddition of a fulvene derivative and a maleimide using a two-pronged approach of combining NMR spectroscopy with computational modelling. Two diastereomers are formed with identical rates in the absence of replication. When replication is enabled, one diastereomer takes over the resources as a "selfish" autocatalyst, while exploiting the competitor as a weak "altruist", resulting in a diastereoselectivity of 16:1. We applied 1D and 2D NMR spectroscopic techniques supported by ab initio chemical shifts as well as ab initio molecular dynamics simulations to study the structure and dynamics of the underlying network. This powerful combination allowed us to decipher the energetic and structural rationale behind the observed behaviour, while static computational methods currently used in the field did not.

Trifluoromethyl-substituted analogues of 1-aminocyclobutane-1-carboxylic acid

Trifluoromethyl-substituted analogues of the 1-amino-cyclobutane-1- carboxylic acid - 1-amino-3-(trifluoromethyl) cyclobutanecarboxylic and 1-amino-3,3-bis(trifluoromethyl)cyclobutane-carboxylic acids - have been synthesized from 1,3-dibromoacetone dimethyl ketal. The key step of the syntheses is a transformation of the acid moiety into the trifluoromethyl group using SF4 and HF. Georg Thieme Verlag Stuttgart.

AZETIDINE AND CYCLOBUTANE DERIVATIVES AS JAK INHIBITORS

The present invention relates to azetidine and cyclobutane derivatives, as well as their compositions, methods of use, and processes for preparation, which are JAK inhibitors useful in the treatment of JAK-associated diseases including, for example, inflammatory and autoimmune disorders, as well as cancer.

AMINO ACID COMPOUNDS

[Problem] To provide novel compounds that are S1P1 receptor agonists and exhibit an immunosuppressive activities by inducing lymphocyte sequestration in secondary lymphoid tissues. In addition, to provide a pharmaceutical agent which comprises the compounds as an effective component, in particular to provide a therapeutic and/or prophylactic agent for an autoimmune disease and the like. [Solving Means] Amino acid compounds that are represented by the following Formula (1) are provided