17159-79-4

Basic information

• Product Name: Ethyl 4-oxocyclohexanecarboxylate
• Synonyms: ETHYL 4-CYCLOHEXANONECARBOXYLATE;ETHYL 4-OXOCYCLOHEXANECARBOXYLATE;ETHYL CYCLOHEXANONE-4-CARBOXYLATE;CYCLOHEXANONE-4-CARBOXYLIC ACID ETHYL ESTER;4-CYCLOHEXANONECARBOXYLIC ACID ETHYL ESTER;4-(ETHOXYCARBONYL)CYCLOHEXANONE;4-OXO-CYCLOHEXANECARBOXYLIC ACID ETHYL ESTER;ethyl 4-oxocyclohexancarboxylate
• CAS NO: 17159-79-4
• Molecular Formula: C₉H₁₄O₃
• Molecular Weight: 170.21
• EINECS: 1806241-263-5
• Product Categories: Drug Intermediates;Esters;Ring Systems;Aliphatics;Intermediates & Fine Chemicals;Pharmaceuticals;Maraviroc;Building Blocks;C8 to C9;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 17159-79-4.mol

Chemical Properties

• Melting Point: 221-226 °C
• Boiling Point: 150-152 °C40 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.068 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0238mmHg at 25°C
• Refractive Index: n20/D 1.461(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform, Methanol
• Water Solubility: insoluble
• BRN: 2520501
• CAS DataBase Reference: Ethyl 4-oxocyclohexanecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 4-oxocyclohexanecarboxylate(17159-79-4)
• EPA Substance Registry System: Ethyl 4-oxocyclohexanecarboxylate(17159-79-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 17159-79-4(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Research:
Ethyl 4-oxocyclohexanecarboxylate is used as a research compound for studying cyclohexanone monooxygenase and its mutants as catalysts. This helps in understanding the enzyme's role in various biological processes and its potential applications in drug development.
2. Used in the Preparation of Dopamine Agonists:
Ethyl 4-oxocyclohexanecarboxylate is used as an intermediate in the synthesis of dopamine agonists, which are important in the treatment of various neurological and psychiatric disorders, such as Parkinson's disease and hyperprolactinemia.
3. Used in the Synthesis of Tetracyclic Diterpenes:
Ethyl 4-oxocyclohexanecarboxylate is employed as a key component in the preparation of the skeleton of tetracyclic diterpenes. These complex organic compounds have diverse applications in the pharmaceutical, agrochemical, and fragrance industries.
4. Used in Chemical Research and Development:
As a cyclohexanone derivative, Ethyl 4-oxocyclohexanecarboxylate is utilized in various chemical research and development processes, particularly in the synthesis of novel compounds and the investigation of their properties and potential applications.

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

Upstream product

• 3618-04-0 4-hydroxycyclohexyl carboxylic acid ethyl ester 
• 99-96-7 4-hydroxy-benzoic acid 
• 72948-75-5 tris-ethyl 3-acetylpentane-1,3,5-tricarboxylate 
• 67-63-0 isopropyl alcohol 
• 55704-60-4 4-oxo-cyclohexane-1,1-dicarboxylic acid diethyl ester 
• 57899-62-4 triethyl 4-oxocyclohexane-1,1,3-tricarboxylate 
• 64-17-5 ethanol 
• 63579-89-5 triethyl pentane-1,3,5-tricarboxylate 
• 72653-21-5 ethyl 1-acetyl-4-oxocyclohexane-1-carboxylate 
• 120-47-8 Ethyl 4-hydroxybenzoate 
• 3618-04-0 trans-4-hydroxy-cyclohexane carboxylic acid ethyl ester 
• 874-61-3 4-oxocyclohexanecarboxylic acid 
• 6940-58-5 pentane-1,3,5-tricarboxylic acid 
• 90942-89-5 ethyl 4-(hydroxyimino)cyclohexane-1-carboxylate 

Downstream Products

• 22650-19-7 4-methoxy-3-cyclohexancarbonsaureethylester 
• 1489-97-0 ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate 
• 93245-98-8 1,4-dioxaspiro[4.5]decane-8-carbaldehyde 
• 322725-63-3 6-fluoro-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid ethyl ester 
• 452333-58-3 ethyl 4-fluorocyclohex-3-ene-1-carboxylate 
• 178312-47-5 ethyl 4,4-difluorocyclohexane-1-carboxylate 
• 628294-72-4 6-methoxy-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid ethyl ester 
• 218779-74-9 ethyl 4-(2-(tert-butoxy)-2-oxoethylidene)cyclohexanecarboxylate 
• 219770-56-6 ethyl 4-(N,N-di(phenylmethyl)amino)cyclohexanecarboxylate 
• 116779-08-9 4,4-bis(4-hydroxyphenyl)cyclohexane carboxylic acid ethyl ester 
• 907211-31-8 6-fluoro-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid 
• 23521-81-5 (1,4-dioxaspiro[4.5]dec-8-yl)methanol 
• 145576-28-9 ethyl 4-methylidenecyclohexanecarboxylate 
• 923266-93-7 ethyl 4,4-dihydroperoxycyclohexanecarboxylate 

Relevant articles and documents

Design and synthesis of orally active dispiro 1,2,4,5-tetraoxanes; Synthetic antimalarials with superior activity to artemisinin

The design and synthesis of dispiro- and spirotetraoxanes through acid-catalyzed cyclocondensation of bis(hydroperoxides) with ketones were investigated. Various modular synthetic methods were used to enable many different analogues to be prepared from common achiral synthetic intermediates and some of the key reactions employed include reductive amination and mixed anhydride amide coupling reactions. The synthesis of 1,2,4,5-tetraoxanes was also dependent on several factors, including the structure of the ketone or aldehyde, temperature, solvent, pH, and the equilibria between the ketone and the precursors of cyclic peroxides. The required 1,2,4,5-tetraoxane was formed by crosscondensation of the bis(hydroperoxide) and the 1,4-cyclohexanedione was obtained in low temperature. Reductive amination of the ketone with various amino compounds also produced compounds in moderate to good quantities.

Mild Functionalization of Tetraoxane Derivatives via Olefin Metathesis: Compatibility of Ruthenium Alkylidene Catalysts with Peroxides

An easy and mild functionalization method of tetraoxane derivatives via olefin metathesis is reported. This reaction offers a new method to afford fully functionalized tetraoxanes in high yields. This method is also utilized in the functionalization of bioactive compounds.

The Silicon-Hydrogen Exchange Reaction: A Catalytic σ-Bond Metathesis Approach to the Enantioselective Synthesis of Enol Silanes

The use of chiral enol silanes in fundamental transformations such as Mukaiyama aldol, Michael, and Mannich reactions as well as Saegusa-Ito dehydrogenations has enabled the chemical synthesis of enantiopure natural products and valuable pharmaceuticals. However, accessing these intermediates in high enantiopurity has generally required the use of either stoichiometric chiral precursors or stoichiometric chiral reagents. We now describe a catalytic approach in which strongly acidic and confined imidodiphosphorimidates (IDPi) catalyze highly enantioselective interconversions of ketones and enol silanes. These "silicon-hydrogen exchange reactions"enable access to enantiopure enol silanes via tautomerizing σ-bond metatheses, either in a deprotosilylative desymmetrization of ketones with allyl silanes as the silicon source or in a protodesilylative kinetic resolution of racemic enol silanes with a carboxylic acid as the silyl acceptor.

An investigation into the role of 2,6-lutidine as an additive for the RuCl3-NaIO4 mediated oxidative cleavage of olefins to ketones

2,6-Lutidine has been identified as a beneficial additive for the oxidative cleavage of olefins to ketones by NaIO4 in the presence of catalytic RuCl3, improving the yield and shortening the reaction times. In the absence of 2,6-lutidine reactions stalled at the diol intermediate with incomplete conversion to the desired ketones. The reaction protocol described herein also avoids the use of harmful solvents such as CCl4 and DCE and is tolerant of a range of functional groups.

SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds having potency in the modulation of NMDA receptor activity. Such compounds can be used in the treatment of conditions such as depression and related disorders. Orally delivered formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

Development of Fluorinated Analogues of Perhexiline with Improved Pharmacokinetic Properties and Retained Efficacy

We designed and synthesized perhexiline analogues that have the same therapeutic profile as the parent cardiovascular drug but lacking its metabolic liability associated with CYP2D6 metabolism. Cycloalkyl perhexiline analogues 6a-j were found to be unsuitable for further development, as they retained a pharmacokinetic profile very similar to that shown by the parent compound. Multistep synthesis of perhexiline analogues incorporating fluorine atoms onto the cyclohexyl ring(s) provided a range of different fluoroperhexiline analogues. Of these, analogues 50 (4,4-gem-difluoro) and 62 (4,4,4′,4′-tetrafluoro) were highly stable and showed greatly reduced susceptibility to CYP2D6-mediated metabolism. In vitro efficacy studies demonstrated that a number of derivatives retained acceptable potency against CPT-1. Having the best balance of properties, 50 was selected for further evaluation. Like perhexiline, it was shown to be selectively concentrated in the myocardium and, using the Langendorff model, to be effective in improving both cardiac contractility and relaxation when challenged with high fat buffer.

Photoinduced Oxidation of Secondary Alcohols Using 4-Benzoylpyridine as an Oxidant

Photoinduced oxidation of secondary alcohols to ketones was achieved by utilizing an equimolar amount of 4-benzoylpyridine as an oxidant. This transformation proceeds at ambient temperature and exhibits high compatibility with polar functionalities including benzoyl, silyl, and methoxymethyl alcohol protecting groups as well as tosyloxy, bromo, sulfonyl, carbamate, ester, and carboxylic acid units. The present oxidation is solely promoted by the action of organic molecules without the aid of metallic reagents. (Chemical Equation Presented).

FLUORO-PERHEXILINE COMPOUNDS AND THEIR THERAPEUTIC USE

The present invention pertains generally to the field of therapeutic compounds. More specifically the present invention pertains to certain fluoro-perhexiline compounds of the following formula (also referred to herein as FPER compounds) that are useful, for example, in the treatment of disorders (e.g., diseases) including, for example, those which are known to be treated with, or known to be treatable with, perhexiline, including, for example, disorders that are ameliorated by the inhibition of carnitine palmitoyltransferase (CPT); cardiovascular disorders such as: angina pectoris; heart failure (HF); ischaemic heart disease (IHD); cardiomyopathy; cardiac dysrhythmia; stenosis of a heart valve; hypertrophic cardiomyopathy (HCM); coronary heart disease; and other disorders, for example, diabetes and cancer. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, for example, in therapy.

CYCLOHEXYL OR PIPERIDINYL CARBOXAMIDE ANTIBIOTIC DERIVATIVES

The invention relates to antibiotic cyclohexyl or piperidinyl carboximide derivatives of formula (I) wherein R1 represents hydrogen, halogen, (C1-C4)alkyl, (C1-C4)alkoxy, cyano or COOR2, R2 being (C1-C4)alkyl;one or two of U, V, W and X represent(s) N and the remaining represent each CH, or, in the case of X, may also represent CRX, RX being a halogen atom;either B represents N and A represents CH2CH2 or CH(OR3)CH2, or B represents CH or C(OR4) and A represents OCH2, CH2CH(OR5), CH(OR6)CH2, CH(OR7)CH(OR8), CH═CH or CH2CH2;each of R3, R4, R5, R6, R7, and R8 represents independently hydrogen, SO3H, PO3H2, CH2OPO3H2 or COR9, R9 being either CH2CH2COOH or such that R9—COOH is naturally occurring amino acid or dimethylaminoglycine;and to salts of such compounds of formula (I).

CYCLOHEXYL OR PIPERIDINYL CARBOXAMIDE ANTIBIOTIC DERIVATIVES

The invention relates to antibiotic cyclohexyl or piperidinyl carboxamide derivatives of formula (I) wherein R1 represents hydrogen, halogen, (C1-C4)alkyl, (C1-C4)alkoxy, cyano or COOR2, R2 being (C1-C4)alkyl; one or two of U, V, W and X represent(s) N and the remaining represent each CH, or, in the case of X, may also represent CRx, Rx being a halogen atom; either B represents N and A represents CH2CH2 or CH(OR3)CH2, or B represents CH or C(OR4) and A represents OCH2, CH2CH(OR5), CH(OR6)CH2, CH(OR7)CH(OR8), CH=CH or CH2CH2; each of R3, R4, R5, R6, R7 and R8 represents independently hydrogen, SO3H, PO3H2, CH2OPO3H2 or COR9, R9 being either CH2CH2COOH or such that R9-COOH is a naturally occurring amino acid or dimethylaminoglycine; and to salts of such compounds of formula (I).