699-61-6

Usage

InChI:InChI=1/C9H14O2/c10-8-4-7-9(11-8)5-2-1-3-6-9/h1-7H2

Upstream product

• 108-94-1 cyclohexanone 
• 107-13-1 acrylonitrile 
• 292638-85-8 acrylic acid methyl ester 
• 185-70-6 1-oxaspiro(2.5)octane 
• 105-36-2 ethyl bromoacetate 
• 1940-19-8 1-vinylcyclohexanol 
• 79-10-7 acrylic acid 
• 922-67-8 propynoic acid methyl ester 
• 183207-21-8 N,N-Dibenzyl-3-(1-hydroxy-cyclohexyl)-propionamide 
• 3395-91-3 Methyl 3-bromopropionate 

Downstream Products

• 69245-96-1 4-(cyclohex-1-en-1-yl)butan-2-one/4-cyclohexylidenebutan-2-one 
• 927-49-1 dipentyl ketone 
• 60416-25-3 3-(cyclohex-1-enyl)propionaldehyde 
• 1394163-03-1 C₁₆H₂₅NO 
• 6963-45-7 1-(3-hydroxypropyl)-cyclohexanol 
• 73089-99-3 1-[2-(1-Hydroxycyclopentyl)ethyl]cyclohexanol 
• 101861-89-6 3-(1-hydroxy-cyclohexyl)-propionic acid amide 
• 65173-43-5 ethyl 3-(cyclohex-1-en-1-yl)propionate 
• 176-91-0 1-oxaspiro<4,5>decane 

Relevant academic research and scientific papers

Samarium (II) iodide-induced intermolecular coupling of a,b-unsaturated esters with ketones: Reactions of methyl propiolate and ethyl buta-2,3-dienoate with cyclohexanone and its application to synthesis of a terpene carboxylic acid

The reactions of methyl propiolate and ethyl buta-2,3-dienoate with cyclohexanone induced by SmI2 occurred either at a- or b-position to yield different products depending on with or without a proton source. The synthesis of terpenic acid was demonstrated using this reaction.

Tandem cross-metathesis/hydrogenation/cyclization reactions by using compatible catalysts

(Matrix presented) A one-pot tandem cross-metathesis/hydrogenation/cyclization procedure was achieved at room temperature, under 1 atm of hydrogen, in the presence of a ruthenium catalyst and PtO2 showing the compatibility of the two catalysts. This tandem reaction allows the synthesis of substituted lactones and lactols from acrylic acid and acrolein, respectively, in the presence of unsaturated alcohols.

Homoaldol and aldol reactions from common enolates and oxirance: Reaction of reductively generated chromium enolates through cationic rearrangement

Enolates generated from α-bromo esters by the reduction with Bu6CrLi3 react with oxiranes to afford γ-hydroxy esters and β-hydroxy esters, depending on the Lewis acid used as a promoter.

Samarium(II) iodide-mediated intermolecular coupling reactions of N,N- dibenzylenamides with carbonyl compounds and transformation of the product, N,N-dibenzyl-γ-hydroxyamide to δ-aminoalcohol

Samarium(II) iodide-mediated intermolecular coupling reactions of N,N- dibenzylenamides (1a-d) with carbonyl compounds (2a-i) produced the corresponding N,N-dibenzyl-γ-hydroxyamides (3a-i) in moderate to good yields. Attempts to remove the two benzyl groups of 3a using hydrogenolysis and Birch reduction were unsuccessful. On the other hand, the lithium aluminum hydride reduction of 3a produced 10 in 61% yield, and dedibenzylation using 20% Pd(OH)2 on carbon gave the corresponding δ- aminoalcohol (11).

Samarium diiodide promoted spirolactonization of cycloalkanones

Reaction of cycloalkanones with methyl 3-bromopropionate and SmI2 afforded formation of spiroanellated γ-lactones, pinacols and unprecedented 3-(1-hydroxycycloalkyl)-1-oxaspiro[n,m]alkan-2-ones.