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

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

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

Downstream Products

• 65277-17-0 2-Amino-cyclohex-1-enecarboxylic acid tert-butyl ester 
• 344758-16-3 2-Oxo-1-pent-2-ynyl-cyclohexanecarboxylic acid tert-butyl ester 
• 104323-54-8 tert-butyl 3-(4'-pentenyl)-2-oxocyclohexanecarboxylate 
• 344449-21-4 tert-butyl 1-benzyl-2-oxocyclohexanecarboxylate 
• 89100-18-5 1-Allyl-2-oxo-cyclohexanecarboxylic acid tert-butyl ester 
• 113655-45-1 methyl 7-(2-oxo-1-t-butoxycarbonylcyclohexyl)hept-5-ynoate 
• 126907-54-8 6-tert. butoxycarbonyl-7-(4-methoxycarbonylphenyl)heptanoic acid methyl ester 
• 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 
• 1381800-83-4 t-butyl 1-azido-2-oxocyclohexanecarboxylate 
• 1381800-60-7 t-butyl 1-chloro-2-oxocyclohexanecarboxylate 
• 1381800-91-4 t-butyl 1-amino-2-oxocyclohexanecarboxylate 
• 1381801-06-4 t-butyl 1-(benzylthio)-2-methyl-3-oxobutyrate 
• 1381801-07-5 t-butyl 1-[(furan-2-yl)methylthio]-2-oxocyclohexanecarboxylate 

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.

Rh2(II)-catalyzed ester migration to afford 3 H-indoles from trisubstituted styryl azides

Rh2(II)-Complexes trigger the formation of 3H-indoles from ortho-alkenyl substituted aryl azides. This reaction occurs through a 4π-electron-5-atom electrocyclization of the rhodium N-aryl nitrene followed by a [1,2]-migration to afford only 3H-indoles. The selectivity of the migration is dependent on the identity of the β-styryl substituent.

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.

Catalytic Michael reactions of ketoesters with a camphor-derived acrylate equivalent: Stereoselective access to all-carbon quaternary centers

(Chemical Equation Presented) A camphor-based α′-hydroxy enone reagent acts as a chiral acrylate equivalent in copper-catalyzed Michael reactions of β-keto esters and affords products that possess all-carbon quaternary stereocenters of high enantiomeric purity.

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.

C/O-Alkylation Ratios in the Ring-Closures of 7-Halo-3-oxo Esters

Four acyclic 7-halo-3-oxo esters have been treated with bases under various conditions to obtain six-membered ring compounds.These halo keto esters give more O-alkylation (C/O = 0.18-3.2) than do the analogous halo ketones.