33371-97-0

Usage

Chemical Properties

clear colorless to slightly yellow liquid

InChI:InChI=1/C8H14O2/c1-2-10-8-6-4-3-5-7(8)9/h8H,2-6H2,1H3/t8-/m1/s1

Upstream product

• 58101-72-7 C₈H₁₅ClOSi 
• 108-94-1 cyclohexanone 
• 73249-96-4 (cyclohex-1-en-1-yloxy)(ethoxy)dimethylsilane 
• 64-17-5 ethanol 
• 286-20-4 cyclohexane-1,2-epoxide 
• 2562-37-0 1-nitrocyclohexene 
• 60308-50-1 2-hydroxycyclohexanone dimer 
• 10499-40-8 2-Ethoxy-cyclohexanonoxim 
• 533-60-8 cyclohexanone-2-ol 

Downstream Products

• 127534-29-6 2-(1-methyl-1H-indol-3-yl)cyclohexan-1-one 
• 228395-56-0 1-ethoxy-2-(hexyloxy)benzene 
• 94259-20-8 1,2-dihexyloxybenzene 
• 4342-47-6 2-ethoxy-cyclohexylamine 
• 94-71-3 2-Ethoxyphenol 
• 804563-81-3 Acetic acid (1S,2S)-1-cyano-2-ethoxy-cyclohexyl ester 
• 804563-81-3 Acetic acid (1S,2R)-1-cyano-2-ethoxy-cyclohexyl ester 
• 6782-77-0 cyclohexane-1,2-dione-bis-phenylhydrazone 

Relevant academic research and scientific papers

Flexible stereoselective functionalizations of ketones through umpolung with hypervalent iodine reagents

The functionalization of carbonyl compounds in the α-position has gathered much attention as a synthetic route because of the wide biological importance of such products. Through polarity reversal, or "umpolung", we show here that typical nucleophiles, such as oxygen, nitrogen, and even carbon nucleophiles, can be used for addition reactions after tethering them to enol ethers. Our findings allow novel retrosynthetic planning and rapid assembly of structures previously accessible only by multistep sequences. A Nu approach: An efficient α-functionalization of ketones with a range of simple and useful nucleophiles is possible by using hypervalent iodine reagents (see scheme; Nu′ can be the Nu itself or a protected form of this nucleophile group).

Ring-opening reactions of epoxides catalyzed by molybdenum(VI) dichloride dioxide

Transformation of epoxides to β-alkoxy alcohols, acetonides, and α-alkoxy ketones is achieved by using molybdenum(VI) dichloride dioxide (MoO2Cl2) as a catalyst. Alcohol, aldehyde, oxime, tosyl, and tert-butyldimethylsilyl functional groups are tolerated during the methanolysis and acetonidation of the functionalized epoxides. No polymerization product is observed with any of the epoxides. Direct conversion of epoxides devoid of sensitive functional groups into the corresponding α-methoxy ketone is achieved in a single step by using the MoO2Cl 2/Oxone system. Georg Thieme Verlag Stuttgart.

Diastereo- and enantioselective synthesis of cis-2- hydroxycyclohexanamine and corresponding ethers by asymmetric reductive amination

A series of homochiral cis-2-alkoxy- and 2-aryloxyeyclohexanamines 5b- 5e has been synthesised by means of asymmetric reductive amination of the corresponding racemic 2-oxygenated cyclohexanones 2 with ee-values ranging from 95 to >99%. The respective 2-hydroxy and 2-cyclohexyl derivatives 5g-5h have been prepared from the 2-phenoxycyclohexanamine 4e. Relative and absolute stereochemistry has been elucidated.

CHEMISTRY OF α-NITROEPOXIDES: SYNTHESIS OF USEFUL INTERMEDIATES VIA NUCLEOPHILIC RING OPENING OF α-NITROEPOXIDES

Various α-nitroepoxides are converted into corresponding 1,2-diketones via two different ways of ring opening viz. with Pd(O) and with DMSO/BF3*EtO2 (or ClSiMe3).In addition to this, a variety of nucleophiles are reacted with α-nitrocyclopentene oxide 6 and α-nitrocyclohexene oxide 7 to form the corresponding α-substituted ketones which are useful intermediates in organic synthesis.Two of the products so obtained viz. 32 and 33 are also transformed further into optically active thialactones 38 and 39 respectively via baker's yeast reduction followed by lactonisation.

A NEW APPROACH TO α-ALKOXY- AND α-ALKYLTHIOKETONES FROM CONJUGATED NITROALKENES

α-Substituted ketones are obtained in two steps by reduction of the α,β-unsaturated nitroalkenes using SnCl2*2H2O in alcoholic media followed by hydrolysis with levulinic acid.

Production of alkoxy phenolic compounds

Alkoxy phenols such as o-methoxyphenol (guaiacol) and o-ethoxyphenol are prepared from substituted cycloaliphatic ketones by dehydrogenation thereof in the presence of a Group VIII noble metal catalyst, preferably palladium supported on carbon, at a temperature of 150° C., to 250° C. The reaction is carried out neat or in the liquid phase using an alicyclic ester reaction solvent having a boiling point ranging from about 150° C., to 250° C. The substituted cycloaliphatic ketone reactant, such as 2-chlorocyclohexanone is prepared by chlorination of cyclohexanone with subsequent conversion of the 2-chlorocyclohexanone to the alkoxy-cyclohexanone compound which is dehydrogenated.

Method for the production of alkoxycyclohexanones

Alkoxy phenols such as o-methoxyphenol (guaiacol) and o-ethoxyphenol are prepared from substituted cycloaliphatic ketones by dehydrogenation thereof in the presence of a Group VIII noble metal catalyst, preferably palladium supported on carbon, at a temperature of 150° to 250° C. The reaction is carried out neat or in the liquid phase using an alicyclic ester reaction solvent having a boiling point ranging from about 150° to 250° C. The substituted cycloaliphatic ketone reactant, such as 2-chlorocyclohexanone is prepared by chlorination of cyclohexanone with subsequent conversion of the 2-chlorocyclohexanone to the alkoxy-cyclohexanone compound which is dehydrogenated.