178312-47-5

Basic information

• Product Name: ETHYL 4,4-DIFLUOROCYCLOHEXANECARBOXYLATE
• Synonyms: ETHYL 4,4-DIFLUOROCYCLOHEXANECARBOXYLATE;Ethyl 4,4-difluorocyclohexanedicarboxylate;Cyclohexanecarboxylic acid, 4,4-difluoro-, ethyl ester (9CI);Cyclohexanecarboxylic acid, 4,4-difluoro-, ethyl ester;4,4-Difluoro-1-(ethoxycarbonyl)cyclohexane;Ethyl 4,4-difluorocyclohexane-1-carboxylate;Ethyl 4,4-dilfuorocyclohexanecarboxylate
• CAS NO: 178312-47-5
• Molecular Formula: C₉H₁₄F₂O₂
• Molecular Weight: 192.2
• EINECS: 1312995-182-4
• Product Categories: CARBOXYLICESTER;Drug Intermediates;Esters;Ring Systems
• Mol File: 178312-47-5.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 84-86°C/8mm
• Flash Point: 84-86°C/8mm
• Appearance: /
• Density: 1.1 g/cm³
• Vapor Pressure: 0.28mmHg at 25°C
• Refractive Index: 1.417
• Storage Temp.: 2-8°C
• CAS DataBase Reference: ETHYL 4,4-DIFLUOROCYCLOHEXANECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 4,4-DIFLUOROCYCLOHEXANECARBOXYLATE(178312-47-5)
• EPA Substance Registry System: ETHYL 4,4-DIFLUOROCYCLOHEXANECARBOXYLATE(178312-47-5)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 178312-47-5(Hazardous Substances Data)

Usage

Uses

4,4-Difluorocyclohexanecarboxylic Acid Ethyl Ester is used as a reactant in the preparation of antiretroviral drug Maraviroc (M193000), which is CCR-5 receptor antagonist used for the treatment of HIV.

InChI:InChI=1/C9H14F2O2/c1-2-13-8(12)7-3-5-9(10,11)6-4-7/h7H,2-6H2,1H3

Upstream product

• 17159-79-4 ethyl 4-oxocyclohexane-1-carboxylate 
• 444578-35-2 ethyl 4,4-dichlorocyclohexanecarboxylate 
• 1072935-22-8 ethyl 4,4-bis(trifluoroacetoxy)cyclohexanoate 
• 874-61-3 4-oxocyclohexanecarboxylic acid 
• 253276-02-7 4-chloro-cyclohex-3-enecarboxylic acid ethyl ester 
• 90942-89-5 ethyl 4-(hydroxyimino)cyclohexane-1-carboxylate 
• 3618-04-0 4-hydroxycyclohexyl carboxylic acid ethyl ester 

Downstream Products

• 122665-97-8 4,4-difluorocyclohexanecarboxylic acid 
• 1443256-99-2 4,4-difluorocyclohexanecarboxylic acid hydrazide 

Relevant articles and documents

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.

Substituted imidazo[1,2-b]pyridazines as protein kinase inhibitors

The present invention provides protein kinase having one of the following structures (I), (II) or (III): or a stereoisomer, prodrug, tautomer or pharmaceutically acceptable salt thereof, wherein R, R1, R2 and X are as defined herein. Compositions and methods for using the same in the treatment of cancer, autoimmune, inflammatory and other Pim kinase-associated conditions are also disclosed.