30132-23-1

Basic information

• Product Name: ethyl 3-bromo-2-oxocyclohexanecarboxylate
• Synonyms: ethyl 3-bromo-2-oxocyclohexanecarboxylate;2-Oxo-3-bromocyclohexanecarboxylic acid ethyl ester;3-Bromo-2-oxo-1-cyclohexanecarboxylic acid ethyl ester;2-Bromo-6-(carbethoxy)cyclohexanone;2-Bromo-6-(ethoxycarbonyl)cyclohexanone;2-Carbethoxy-6-bromocyclohexanone;6-Bromo-2-(carbethoxy)cyclohexanone;Ethyl 6-bromocyclohexanone-2-carboxylate
• CAS NO: 30132-23-1
• Molecular Formula: C₉H₁₃BrO₃
• Molecular Weight: 249.10172
• EINECS: 250-065-6
• Mol File: 30132-23-1.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 295.9°Cat760mmHg
• Flash Point: 132.7°C
• Appearance: /
• Density: 1.453
• Vapor Pressure: 0.00148mmHg at 25°C
• Refractive Index: 1.5280
• Storage Temp.: -20°C Freezer
• Solubility: Acetone; Dichloromethane; Ethyl Acetate; Methanol
• PKA: 10.39±0.40(Predicted)
• CAS DataBase Reference: ethyl 3-bromo-2-oxocyclohexanecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3-bromo-2-oxocyclohexanecarboxylate(30132-23-1)
• EPA Substance Registry System: ethyl 3-bromo-2-oxocyclohexanecarboxylate(30132-23-1)

Safety Data

• Hazardous Substances Data: 30132-23-1(Hazardous Substances Data)

Usage

Uses

Ethyl 3-Bromo-2-oxocyclohexanecarboxylate is an intermediate in the synthesis of trans-1,2-Dimethylcyclopentane (D464925). trans-1,2-Dimethylcyclopentane was found in sedimentary rocks and was one of the hydrocarbons used to determine its maturation history.

InChI:InChI=1/C9H13BrO3/c1-2-13-9(12)6-4-3-5-7(10)8(6)11/h6-7H,2-5H2,1H3

Upstream product

• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 7726-95-6 bromine 
• 35244-45-2 ethyl-2-(1-piperidinyl)-1-cyclohexenecarboxylate 
• 35244-51-0 ethyl-2-(1-piperidinyl)-2-cyclohexenecarboxylate 

Downstream Products

• 3400-80-4 ethyl 2-oxocyclohex-3-ene-1-carboxylate 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 118-61-6 2-hydroxy-benzoic acid ethyl ester 
• 76488-64-7 2-(4-Ethoxy-phenylamino)-4,5,6,7-tetrahydro-benzothiazole-4-carboxylic acid ethyl ester 
• 76488-56-7 2-(2-Bromo-phenylamino)-4,5,6,7-tetrahydro-benzothiazole-4-carboxylic acid ethyl ester 
• 76488-63-6 2-(2-Ethoxy-phenylamino)-4,5,6,7-tetrahydro-benzothiazole-4-carboxylic acid ethyl ester 
• 50483-99-3 trans-DL-1,2-cyclopentanedicarboxylic acid 
• 71911-75-6 ethyl C-<3-(ethoxycarbonyl)-2-oxocyclohexyl>malonate 
• 76488-61-4 2-(2-Methoxy-phenylamino)-4,5,6,7-tetrahydro-benzothiazole-4-carboxylic acid ethyl ester 
• 49844-36-2 6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylic acid ethyl ester 
• 1461-96-7 cis-1,2-cyclopentanedicarboxylic acid 
• 33814-66-3 ethyl 2-phenyl-4,5,6,7-tetrahydro-4H-cyclohexa[d]thiazole-4-carboxylate 
• 882490-17-7 (S)-(2-phenyl-4,5,6,7-tetrahydrobenzo[d]thiazol-4-yl)methanol 
• 882490-20-2 (S)-(2-phenyl-4,5,6,7-tetrahydrobenzo[d]thiazol-4-yl)methyl 4-methylbenzenesulfonate 

Relevant articles and documents

Construction of the Fused Pentacycle of Talatisamine via a Combination of Radical and Cationic Cyclizations

The fused 6/7/5/6/6-membered (ABCDE) ring system of talatisamine was synthesized in 22 steps. After preparation of the AE-ring structure from 2-(ethoxycarbonyl)cyclohexanone, elaboration of the carboskeleton was realized by sequential additions of allyl magnesium bromide and the lithiated C-ring. The C11-bridgehead radical derived from the ACE-ring underwent the 7-endo cyclization with the enone moiety to form the B-ring in C10-stereoselective and C11-stereospecific manners. The 6-endo cyclization of the remaining D-ring was in turn attained by using the silyl enol ether as the nucleophile and the PhSeCl-activated olefin as the electrophile. These radical and cationic cyclizations were demonstrated to be highly chemoselective, and they significantly contributed to streamlining the route to the intricately fused pentacycle of talatisamine.

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