1655-07-8

Basic information

• Product Name: Ethyl 2-oxocyclohexanecarboxylate
• Synonyms: 2-oxo-cyclohexanecarboxylicaciethylester;Ethyl 1-oxo-2-cyclohexanecarboxylate;Ethyl 2-cyclohexanone-1-carboxylate;Ethyl 2-oxo-1-cyclohexanecarboxylate;Ethyl 2-oxocylohexanecarboxylate;Ethyl 2-oxylcyclohexanecarboxylic;AKOS 91391;AKOS MSC-0386
• CAS NO: 1655-07-8
• Molecular Formula: C₉H₁₄O₃
• Molecular Weight: 170.21
• EINECS: 216-731-5
• Product Categories: API intermediates;Building Blocks;C8 to C9;Carbonyl Compounds;Chemical Synthesis;Esters;Organic Building Blocks
• Mol File: 1655-07-8.mol

Chemical Properties

• Melting Point: 101 °C
• Boiling Point: 106 °C11 mm Hg(lit.)
• Flash Point: 185 °F
• Appearance: Clear colorless to pale yellow liquid
• Density: 1.064 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.065mmHg at 25°C
• Refractive Index: n20/D 1.477(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Sparingly), Methanol (Sparingly)
• PKA: 12.06±0.20(Predicted)
• Water Solubility: Soluble in water.
• BRN: 608356
• CAS DataBase Reference: Ethyl 2-oxocyclohexanecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2-oxocyclohexanecarboxylate(1655-07-8)
• EPA Substance Registry System: Ethyl 2-oxocyclohexanecarboxylate(1655-07-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-37/39-26-36
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 1655-07-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Ethyl 2-oxocyclohexanecarboxylate is used as a chemical intermediate for the production of other chemicals. For example, it can react with 4-methyl-aniline to obtain 2-oxo-cyclohexanecarboxylic acid p-toluidide. The reaction occurs with the reagent DMAP.
Used in Biocatalysis:
Ethyl 2-oxocyclohexanecarboxylate is also utilized in biocatalysis, a process that employs biological catalysts, such as enzymes, to facilitate chemical reactions. This application allows for more efficient and environmentally friendly synthesis of target compounds.

Synthesis Reference(s)

Canadian Journal of Chemistry, 42, p. 1333, 1964 DOI: 10.1139/v64-205The Journal of Organic Chemistry, 53, p. 878, 1988 DOI: 10.1021/jo00239a038Tetrahedron Letters, 7, p. 2201, 1966

InChI:InChI=1/C9H14O3/c1-2-12-9(11)7-5-3-4-6-8(7)10/h7H,2-6H2,1H3/t7-/m0/s1

Upstream product

• 108-75-8 2,4,6-trimethyl-pyridine 
• 34243-82-8 1-bromo-2-oxo-cyclohexanecarboxylic acid ethyl ester 
• 91-22-5 quinoline 
• 30132-23-1 ethyl 3-bromo-2-oxocyclohexanecarboxylate 
• 2050-20-6 diethyl pimelate 
• 141-52-6 sodium ethanolate 
• 3779-30-4 pentane-1,1,5,5-tetracarboxylic acid tetraethyl ester 
• 1655-06-7 (1R,2S)-ethyl 2-hydroxycyclohexanecarboxylate 
• 102369-46-0 6-oxo-cyclohex-3-enecarboxylic acid ethyl ester 
• 15219-34-8 Oxalyl bromide 
• 108-94-1 cyclohexanone 
• 95-92-1 oxalic acid diethyl ester 
• 60-29-7 diethyl ether 
• 105-58-8 Diethyl carbonate 

Downstream Products

• 855600-28-1 1-(5-methoxy-1-methyl-2-oxo-indolin-3-ylidenemethyl)-2-oxo-cyclohexanecarboxylic acid ethyl ester 
• 93865-05-5 3-(1-ethoxycarbonyl-2-oxo-cyclohexyl)-propionic acid ethyl ester 
• 38778-80-2 2-p-anisidino-cyclohex-1-enecarboxylic acid ethyl ester 
• 6279-91-0 ethyl 2-oxo-1-propylcyclohexanecarboxylate 
• 27334-56-1 1-methoxymethyl-2-oxo-cyclohexanecarboxylic acid ethyl ester 
• 25096-42-8 1-Ethoxycarbonyl-cyclohexen-⁽¹⁾-ol-⁽²⁾-methoxymethylaether 
• 69881-57-8 2-oxo-1-(3-oxo-butyl)-cyclohexanecarboxylic acid ethyl ester 
• 25342-01-2 2-cyanomethylene-cyclohexanecarboxylic acid ethyl ester 
• 83051-34-7 3-methyl-7,8,9,10-tetrahydro-6H-dibenzopyran-6-one 
• 19178-21-3 2-methyl-5,6,7,8-tetrahydronquinazolin-4(3H)-one 
• 61771-75-3 ethyl 1-allyl-2-oxocyclohexanecarboxylate 
• 42894-09-7 ethyl 1-(2-cyanoethyl)-2-oxocyclohexanecarboxylate 
• 16064-21-4 2-sulfanylidene-1,2,3,4,5, 6,7,8-octahydroquinazolin-4-one 
• 106421-32-3 methyl 2-oxo-1-(2’-methoxycarbonylethyl)cyclohexanecarboxylate 

Relevant articles and documents

Phosphate tricyclic coumarin analogs as steroid sulfatase inhibitors: Synthesis and biological activity

In the present work, we report convenient methods for the synthesis and biological evaluation of phosphate tricyclic coumarin derivatives as potential steroid sulfatase inhibitors. The described synthesis includes the straightforward preparation of 7-hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one, 3-hydroxy-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one and 3-hydroxy-8,9,10,11-tetrahydro-7H-cyclohepta[c]chromen-6-one modified with various phosphate moieties. The inhibitory effects of the synthesized compounds were tested on STS isolated from human placenta as well as the MCF-7, MDA-MB-231 and MDA-MB-435S cancer cell lines. Most of the new STS inhibitors possessed IC50 values between 21 to 159 μM. In the course of our investigation, the largest inhibitory effects in the STS enzyme assays were observed for the three compounds 9p, 9r and 9s, with IC50 values of 36.4, 37.8 and 21.5 μM, respectively (IC50 value of 1.0 μM for the 665-COUMATE used as a reference). The compound 9r, exhibited the highest potency against MCF-7, an estrogen receptor positive (ER+) cell line, with a GI50 value of 24.7 μM. The structure-activity relationships of the synthesized coumarin derivatives with the STS enzyme are discussed.

Solvent-free Dieckmann condensation reactions of diethyl adipate and pimelate

Dieckmann condensation reactions of diethyl adipate and pimelate proceeded efficiently in the absence of solvent, and the reaction products were collected by a direct distillation from the solvent-free reaction mixture.

Enantioselective α-Amination of Acyclic 1,3-Dicarbonyls Catalyzed by N-Heterocyclic Carbene

Herein, we describe a method for the catalytic enantioselective α-amination of α-substituted acyclic 1,3-ketoamides and 1,3-amidoesters that affords the products possessing N-substituted quaternary stereocenters with a chiral N-heterocyclic carbene (NHC). The reaction is based on the utilization of an intrinsic Br?nsted base characteristic of NHC that enables the catalytic formation of a chiral ion pair comprising the enolate and the azolium ion. A series of challenging open-chain α-substituted 1,3-dicarbonyls are aminated via this method with ee's of ≤99%.

Radical Aza-Cyclization of α-Imino-oxy Acids for Synthesis of Alkene-Containing N-Heterocycles via Dual Cobaloxime and Photoredox Catalysis

Nitrogen-containing heterocycles are prevalent in both naturally and synthetically bioactive molecules. We report herein an unprecedented protocol for radical aza-cyclization of α-imino-oxy acids with pendant alkenes via synergistic photoredox and cobaloxime catalysis. With or without alkenes as the intermolecular cross-coupling partners, the transformation provides a variety of corresponding alkene-containing dihydropyrrole products in satisfactory yields. In the presence of external alkenes, the tandem reaction generates E-selective coupling products with excellent chemo- and stereoselectivity.

Cobalt-Catalyzed Cross-Couplings between Alkenyl Acetates and Aryl or Alkenyl Zinc Pivalates

CoBr2 (5 mol %) in the presence of 2,2′-bipyridyl (5 mol %) enables electrophilic alkenylations between easily accessible alkenyl acetates or tosylates and various functionalized aryl zinc pivalates at ambient temperature. This cobalt-catalyzed

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Regioselective catalytic asymmetric C-alkylation of isoxazolinones by a base-free palladacycle-catalyzed direct 1,4-addition

Isoxazolinones constitute a class of heterocycles utilized for the development of novel drug candidates. The cyclic oxime ester motif is also synthetically useful as it contains functional handles which have previously been used to provide access to an assortment of valuable compound classes not easily accessible by alternative approaches. However, asymmetric methods towards isoxazolinones are notoriously scarce. Herein we report the first catalytic asymmetric alkylations of isoxazolinones forming all-C-substituted quaternary stereocenters. The present studies were driven by the question of how to control the regioselectivity in the competition of different nucleophilic positions. The investigation of a direct 1,4-addition uncovered that a sterically demanding palladacycle catalyst directs the reactivity in the absence of a base nearly exclusively to the nucleophilic C atom, while at the same time it allows for high enantioselectivity and TONs up to 1900.

Selective transformations of carbonyl functions in the presence of α,β-unsaturated ketones: Concise asymmetric total synthesis of decytospolides A and B

Enones selectively react with a combination of PPh3 and TMSOTf to produce phosphonium silyl enol ethers, which work as protective groups of enones during the reduction of other carbonyl functions and can be easily deprotected to regenerate parent enones at workup. Furthermore, the first ketone selective alkylations in the presence of enones were also accomplished. This in situ protection method was applied to concise asymmetric total syntheses of decytospolides A and B.

1-(Arylmethyl)-5,6,7,8-tetrahydroquinazolline-2,4-diones and Analogs and the Use Thereof

Disclosed are novel 1-(arylmethyl)-5,6,7,8-tetrahydroquinazoline-2,4-diones and analogs thereof, represented by the Formula I, wherein Ar, A, B, R3-R6 are defined herein. Compounds having Formula I are PARP inhibitors. Therefore, compounds of the invention may be used to treat clinical conditions that are responsive to the inhibition of PARP activity, such as cancer.

Synthesis of five-and six-membered 1,3,3-trimethyl-2-(trimethylsilyl) cycloalkenes: A novel preparation of alkyl/alkenyl/aryl 2,5,5-trimethyl-1- cyclopentenyl ketones

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