15378-40-2

Upstream product

• 52939-54-5 4-cyclohexylhepta-1,6-dien-4-ol 
• 79646-42-7 (E)-1-cyclohexyl-2-buten-1-ol 
• 244176-58-7 5-bromomethyl-3-cyclohexylisoxazoline 
• 63511-92-2 (E)-crotonaldehyde diethyl acetal 
• 1088-01-3 tricyclohexylborane 
• 4630-82-4 methyl cyclohexylcarboxylate 
• 18736-82-8 1-cyclohexyl-but-2-en-1-ol 
• 69036-26-6 1-cyclohexyl-3-buten-1-ol 
• 95123-13-0 1-cyclohexylbut-3-en-1-one 
• 2043-61-0 cyclohexanecarbaldehyde 
• 64-17-5 ethanol 
• 931-48-6 2-cyclohexylacetylene 
• 542-18-7 cyclohexyl chloride 
• 106-95-6 allyl bromide 

Downstream Products

• 97060-51-0 (3RS,1'RS)- and (3RS,1'SR)-3-(3'cyclohexyl-1'-methyl-3'-oxopropyl)1-methyl-2-pyrrolidinone 
• 122968-89-2 (E,3RS,1'RS)-3-(1'-cyclohexyl-1'-hydroxy-2'-butenyl)-1-methyl-2-pyrrolidinone 
• 97060-50-9 3-(1-cyclohexyl-1-hydroxy-2-butenyl)-N-methylpyrrolidone 
• 164595-88-4 (2'RS,3'RS)- and (2'RS,3'SR)-1-(5'-cyclohexyl-2',3'-dimethyl-1',5'-dioxopentyl)pyrrolidine 
• 122969-86-2 (E,2'RS,3'SR)-1-(3'-cyclohexyl-3'-hydroxy-2'methyl-1'-oxo-4'-hexenyl)pyrrolidine 
• 122968-56-3 (E,2'RS,3'RS)-1-(3'-cyclohexyl-3'-hydroxy-2'methyl-1'-oxo-4'-hexenyl)pyrrolidine 
• 97060-47-4 N-(3-cyclohexyl-3-hydroxy-2-methyl-4-hexenoyl)pyrrolidine 
• 62106-65-4 Cyclohexyl 2-methylpropyl ketone 
• 1415351-65-3 (E,S)-S-4-cyclohexylbut-3-en-2-yl 1H-imidazole-1-carbothioate 
• 1613417-22-3 (S)-(E)-S-4-cyclohexyl-2-(3-methoxyphenyl)but-3-en-2-yl methylcarbamothioate 
• 79646-42-7 (2E,1R)-1-cyclohexyl-2-buten-1-ol 
• 18736-82-8 (2E,1S)-1-cyclohexyl-2-buten-1-ol 
• 1613417-12-1 (S)-(E)-S-4-cyclohexylbut-3-en-2-yl 1H-indol-6-yl(methyl)carbamothioate 
• 1613417-10-9 (S)-(E)-tert-butyl 6-((((4-cyclohexylbut-3-en-2-yl)thio)carbonyl)(methyl)amino)-1H-indole-1-carboxylate 

Relevant academic research and scientific papers

A new palladium-catalysed synthesis of 1,1-dialkylbuta-1,3-dienes via organoboron intermediates

Iodobenzene and tetrakis(triphenylphosphine)palladium(0) [(C6H5)3P]4Pd catalyse a new synthesis of 1,1-dialkylbuta-1,3-dienes, starting from 1,1-diethoxybut-2-ene and trialkylboranes, in the presence of Schlosser's superbase LIC-KOR.

Tuning of α-Silyl Carbocation Reactivity into Enone Transposition: Application to the Synthesis of Peribysin D, E-Volkendousin, and E-Guggulsterone

A reliable method for enone transposition has been developed with the help of silyl group masking. Enantio-switching, substituent shuffling, and Z-selectivity are the highlights of the method. The developed method was applied for the first total synthesis of peribysin D along with its structural revision. Formal synthesis of E-guggulsterone and E-volkendousin was also claimed using a short sequence.

Cooperative Electrocatalytic and Chemoselective Alcohol Oxidation by Shvo's Catalyst

A new electrocatalytic conversion of alcohols to ketones and aldehydes was developed based on an electrochemical study of Shvo's complex. The oxidation of secondary alcohols was efficiently performed under mild conditions using a catalytic amount of Shvo's catalyst, in combination with a sub-stoichiometric amount of 2,6-dimethoxy-1,4-benzoquinone in N,N-dimethylformamide at 80 °C. The hydroquinone thus formed is continuously reoxidized with the aid of an electrochemical device. Excellent yields for different ketones, aromatic as well as aliphatic and α,β-unsaturated ketones, are obtained. In addition, chemoselectivity towards oxidation of the secondary alcohol is achieved when converting vicinal diols such as 1,2-octanediol and 1,2-decanediol. (Figure presented.).

Dihydrothiophenes containing quaternary stereogenic centres by sequential stereospecific rearrangements and ring-closing metathesis

Stereospecific [3,3]-sigmatropic rearrangement of O-substituted thiocarbamate derivatives of enantiopure allylic alcohols provides allylic thiocarbamates as single enantiomers. Intramolecular arylation by rearrangement of their allyllithium derivatives provides allylic tertiary thiols. Allylation and ring-closing metathesis gives 2,5-dihydrothiophenes containing sulfur-bearing quaternary centres. This journal is the Partner Organisations 2014.

Iron-catalyzed aerobic oxidation of allylic alcohols: The issue of C=C bond isomerization

An aerobic oxidation of allylic alcohols using Fe(NO3) 3·9H2O/TEMPO/NaCl as catalysts under atmospheric pressure of oxygen at room temperature was developed. This eco-friendly and mild protocol provides a convenient pathway to the synthesis of stereodefined α,β-unsaturated enals or enones with the retention of the C-C double-bond configuration.

Synthesis of Z-alkenes from Rh(I)-catalyzed olefin isomerization of β,γ-unsaturated ketones

Developing olefin isomerization reactions to reach kinetically controlled Z-alkenes is challenging because formation of trans-alkenes is thermodynamically favored under the traditional catalytic conditions using acids, bases, or transition metals as the catalysts. A new synthesis of Z-alkenes from Rh(I)-catalyzed olefin isomerization of β,γ-unsaturated ketones to α,β-unsaturated ketones was developed, providing an easy and efficient way to access various Z-enones.

Difluoro-λ3-bromane-induced oxidative carbon-carbon bond-forming reactions: Ethanol as an electrophilic partner and alkynes as nucleophiles

Reported here for the first time are the oxidative couplings of alkynes and primary alcohols yielding conjugated enones. Although the BF3-catalyzed reaction of terminal alkynes with p-trifluoromethylphenyl(difluoro)-λ3-bromane results in the fluoro-λ3-bromanation of triple bonds to afford (E)-β-fluorovinyl-λ3-bromanes, reaction of an alkyne with the difluoro-λ3-bromane in the presence of an alcohol and BF3-Et2O affords directly conjugated enones in good yields. The reaction proceeds in a highly stereo- and regioselective manner under metal-free conditions. Interestingly, no formation of enones was detected, when difluoro-λ3-iodane p-CF3C6H4IF2 was used instead of the λ3-bromane. A mechanism involving a λ3-bromane-induced oxidation of an alcohol to an aldehyde, [2 + 2] cyclization with alkynes yielding 2H-oxetes, and finally the electrocyclic ring opening is discussed. Copyright

Chromium catalyzed oxidation of (homo-)allylic and (homo-)propargylic alcohols with sodium periodate to ketones or carboxylic acids

Primary and secondary (homo-)allylic and (homo-)propargylic alcohols can be oxidized under slightly acidic conditions at or below room- temperature with sodium periodate in the presence of sodium dichromate as the catalyst to the corresponding carboxylic acids and ketones, respectively.

Ring opening of 5-(bromomethyl)-2-isoxazolines with magnesium metal in absolute MeOH

Ring opening of 5-(bromomethyl)- and 5-(phenylsulfonylmethyl)-2- isoxazolines with magnesium in absolute methanol at -23 °C and room temperature afforded regiospecifically β,γ-enoximes and (E)-α,β-enoximes, respectively.

Homogeneous chromium(VI)-catalyzed oxidations of allylic alcohols by alkyl hydroperoxides: Influence of the nature of the alkyl group on the product distribution

The chromium oxide-catalyzed oxidation of allylic alcohols - R1CH(OH)CR2=CHR3 - by ROOH (R= t-Bu, PhCMe2) affords generally a mixture of R1COCR2=CHR3 and R1CH=CR2COR3. The rate of the reaction and the ratio between the two oxidized compounds both depend on the nature of R. It has been concluded that the oxidative species and the reactive intermediates contain this R group.