65093-64-3

Basic information

• Product Name: 1-Cyclohexene-1-acetic acid, 3-oxo-, ethyl ester
• CAS NO: 65093-64-3
• Molecular Formula: C10H14O3
• Molecular Weight: 182.219
• Mol File: 65093-64-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-Cyclohexene-1-acetic acid, 3-oxo-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Cyclohexene-1-acetic acid, 3-oxo-, ethyl ester(65093-64-3)
• EPA Substance Registry System: 1-Cyclohexene-1-acetic acid, 3-oxo-, ethyl ester(65093-64-3)

Safety Data

• Hazardous Substances Data: 65093-64-3(Hazardous Substances Data)

Upstream product

• 4969-01-1 1,4-dioxaspiro[4.5]decan-7-one 
• 105-36-2 ethyl bromoacetate 
• 105694-62-0 ethyl (3-hydroxy-1-cyclohexenyl)ethanoate 
• 504-02-9 1,3-cylohexanedione 
• 930-68-7 cyclohexenone 
• 22406-80-0 ethyl 2-(1-hydroxycyclohex-2-enyl)acetate 
• 5682-75-7 3-chloro-2-cyclohexenone 
• 35116-15-5 Dibasic magnesium salt of ethyl hydrogen malonate 

Downstream Products

• 927831-75-2 ethyl (E/Z)-2-{3-[(trimethylsilyl)oxy]cyclohex-2-en-1-yliden}acetate 
• 98959-73-0 (3-oxo-cyclohex-1-enyl)-acetic acid methylamide 
• 99062-44-9 3-(2-methylamino-ethyl)-cyclohex-2-enone 
• 103206-14-0 ((E)-3-ethoxy-cyclohex-2-enyliden)-acetic acid 
• 103206-14-0 ((Z)-3-ethoxy-cyclohex-2-enyliden)-acetic acid 
• 105640-85-5 [2-((E)-3-ethoxy-cyclohex-2-enyliden)-ethyl]-methyl-amine 
• 40996-91-6 3-vinyl-cyclohex-2-enone 
• 927831-76-3 ethyl 2-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)sulfanyl]-2-(3-oxocyclohex-1-en-1-yl)acetate 
• 106168-04-1 (3-ethoxy-cyclohex-2-enyliden)-acetic acid ethyl ester 
• 100378-61-8 2-(3-oxocyclohex-1-enyl)acetic acid 

Relevant articles and documents

Chemo-Enzymatic Oxidative Rearrangement of Tertiary Allylic Alcohols: Synthetic Application and Integration into a Cascade Process

A chemo-enzymatic catalytic system, comprised of Bobbitt's salt and laccase from Trametes versicolor, allowed the [1,3]-oxidative rearrangement of endocyclic allylic tertiary alcohols into the corresponding enones under an Oxygen atmosphere in aqueous media. The yields were in most cases quantitative, especially for the cyclopent-2-en-1-ol or the cyclohex-2-en-1-ol substrates without an electron withdrawing group (EWG) on the side chain. Transpositions of macrocyclic alkenols or tertiary alcohols bearing an EWG on the side chain were instead carried out in acetonitrile by using an immobilized laccase preparation. Dehydro-Jasmone, dehydro-Hedione, dehydro-Muscone and other fragrance precursors were directly prepared with this procedure, while a synthetic route was developed to easily transform a cyclopentenone derivative into trans-Magnolione and dehydro-Magnolione. The rearrangement of exocyclic allylic alcohols was tested as well, and a dynamic kinetic resolution was observed: α,β-unsaturated ketones with (E)-configuration and a high diastereomeric excess were synthesized. Finally, the 2,2,6,6-tetramethyl-1-piperidinium tetrafluoroborate (TEMPO+BF4?)/laccase catalysed oxidative rearrangement was combined with the ene-reductase/alcohol dehydrogenase cascade process in a one-pot three-step synthesis of cis or trans 3-methylcyclohexan-1-ol, in both cases with a high optical purity. (Figure presented.).

Novel PDC catalyzed oxidative rearrangement of tertiary allylic alcohols to β-substituted enones

Novel pyridinium dichromate (PDC) catalyzed oxidative rearrangement for the conversion of tertiary allylic alcohols to ?-substituted enones is described. Using a catalytic amount of PDC with PhI(OAc)2 as a co-oxidant in the presence of magnesium sulfate and water under oxygen was found effective for this rearrangement.