137334-09-9

Basic information

• Product Name: tert-butyl 2-oxocyclohexanecarboxylate
• CAS NO: 137334-09-9
• Molecular Weight: 198.262
• Mol File: 137334-09-9.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: tert-butyl 2-oxocyclohexanecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 2-oxocyclohexanecarboxylate(137334-09-9)
• EPA Substance Registry System: tert-butyl 2-oxocyclohexanecarboxylate(137334-09-9)

Safety Data

• Hazardous Substances Data: 137334-09-9(Hazardous Substances Data)

Upstream product

• 1056477-06-5 2-bromocyclohexanone 
• 201230-82-2 carbon monoxide 
• 75-65-0 tert-butyl alcohol 
• 111-16-0 heptanedioic acid 
• 5176-27-2 N-tert-butyloxycarbonyl-pyrrole 
• 108-94-1 cyclohexanone 
• 55623-59-1 di-tert-butyl pimelate 
• 142-79-0 pimeloyl chloride 

Downstream Products

• 104323-54-8 tert-butyl 3-(4'-pentenyl)-2-oxocyclohexanecarboxylate 
• 1034980-92-1 (R)-tert-butyl 1-[3-[(2R)-2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl]-3-oxo-propyl]-2-oxocyclohexanecarboxylate 
• 1158184-27-0 (S,E)-2-oxo-1-(3-oxo-3-phenyl-prop-1-enyl)-cyclohexanecarboxylic acid tert-butyl ester 

Relevant articles and documents

Williamson Ether Synthesis with Phenols at a Tertiary Stereogenic Carbon: Formal Enantioselective Phenoxylation of β-Keto Esters

The enantioselective formation of α-aryloxy-β-keto esters is described for the first time. Lewis acid catalyzed enantioselective chlorination of β-keto esters and subsequent SN2 reactions with phenols yielded α-aryloxy-β-keto esters with up to 96 % ee. Favorskii rearrangement of α-chloro-β-keto esters was also found to give 1,2-diesters with slightly reduced enantiopurity.

Highly enantioselective chlorination of β-keto esters and subsequent SN2 displacement of tertiary chlorides: A flexible method for the construction of quaternary stereogenic centers

Highly enantioselective chlorination of β-oxo esters and subsequent stereospecific substitution of tertiary chlorides are described. Enantioselective chlorination of β-keto esters and malonates was performed using a chiral Lewis acid catalyst prepared from Cu(OTf)2 and the newly developed spirooxazoline ligand 2 to yield the desired α-chlorinated products with high enantioselectivity (up to 98% ee). Nucleophilic substitution of the resulting chlorides proceeded smoothly to afford a variety of chiral molecules such as α-amino, α-alkylthio, and α-fluoro esters, without loss of enantiopurity. The results of X-ray crystallographic analysis proved that Walden inversion occurs at the chlorinated tertiary carbon center. These results supported the fact that the substitution proceeds via an S N2 mechanism.

Preparation of β-oxoesters by carbonylation of α-haloacyl derivatives

A one-pot method for the preparation of β-oxoesters by carbonylation of α-haloacyl derivatives using PdCl2 (PPh3)2-EtNCH2C6H5Cl-NaOAc system as a catalyst is described.