50557-37-4

Upstream product

• 76644-52-5 rac-3-acetoxycyclohexene 
• 57466-29-2 Acetic acid (1S,4S)-4-hydroxy-cyclohex-2-enyl ester 
• 141986-92-7 C₁₈H₂₂O₆ 
• 141986-90-5 C₁₄H₁₆O₃ 
• 57466-29-2 cis-2-cyclohexene-1,4-diol monoacetate 
• 91923-19-2 1-acetoxy-4-trifluoroacetoxy-2-cyclohexene 
• 91923-19-2 trans-4-acetoxy-1-trifluoroacetoxy-cyclohex-2-ene 
• 141986-89-2 C₁₄H₁₆O₂ 
• 2886-59-1 1-methoxycyclohexa-1,4-diene 

Relevant academic research and scientific papers

The thio-adduct facilitated, enzymatic kinetic resolution of 4-hydroxycyclopentenone and 4-hydroxycyclohexenone

The addition of 3,4-dimethoxybenzyl thiol 8, as a benzyl thiol surrogate, to racemic 4-hydroxycyclopent-2-enone 2 and 4-hydroxycyclohex-2-enone 15 gave the corresponding cis-adducts (±)-3-(3,4-dimethoxybenzylthio)-4- hydroxycyclopentanone 4b and (±)-3-(3,4-dimethoxybenzylthio)-4- hydroxycyclohexanone 16 with good diastereocontrol. In both cases, subsequent treatment with vinyl acetate, in the presence of a lipase enabled enantiomer resolution. Thus, (+)-16 and the acetate of its enantiomer, (-)-(1R,2S)-2-(3,4- dimethoxybenzylthio)-4-oxocyclohexyl acetate, (-)-17 were isolated in 98% enantiomeric excess. Based on the 1,4-dioxygenation pattern, (-)-17 can be used to prepare both enantiomers of 4-(tert-butyldimethylsilyloxy)cyclohex-2-enone 19. Firstly, saponification, with a sub-stoichiometric amount of NaOMe, followed by a one-pot silyl ether formation-sulfide elimination sequence gave (+)-19. Then using the same starting material a 6-step sequence, featuring a diastereoselective NaBH4 reduction and a Cope-type sulfoxide elimination, gave (-)-19.

Synthesis of (±) cyclohexane-1(R), 2(R), 4(R)-triol-triphosphate, a deoxygenated analog of myo-inositol-1,4,5-triphosphate

For the use in the studies of inositol-phosphates, (±) cyclohexane-1(R), 2(R), 4(R)-triol-triphosphate 2 was synthesized from anisole. The synthesis used 1,2-benzenedimethanol as a ketone and phosphate protective group which induced easy crystallization of the intermediates. Regeneration of the free ketone 9 under mild conditions followed by its selective reduction and phosphorylation by the phosphite method gave the expected compound 2.

1-ACETOXY-2-CYCLOHEXENE OXIDATION IN THE PRESENCE OF MOLYBDENUM, VANADIUM AND CHROMIUM COMPOUNDS

A study has been made on the catalytic oxidation of ACH-2 with molecular oxygen.The composition of reaction products (1-acetoxy-2-cyclohexene-4-one, 1-acetoxy-2-cyclohexene-4-ol) and their formation pathway have been analyzed.In MoO2(acac)2 catalysis, 1-acetoxy-2,3-epoxycyclohexane is formed. In an ACH-2 medium, the catalytic HP-decomposition mechanism and reaction yields have been investigated.The HP-decomposition have been shown to proceed through intermediate complexes over catalysts with the following overall decomposition rate constants: The hydroperoxide decomposes mainly heterolytically in the presence of MoO2(acac)2.With Cr(acac)2 the radical decomposition fraction amounts to under 1percent.

PALLADIUM-CATALYZED 1,4-ACETOXY-TRIFLUOROACETOXYLATION OF 1,3-DIENES

Palladium-catalyzed oxidation of conjugated dienes in acetic acid containing CF3COOH/LiOOCCF3 results in the formation of 1-acetoxy-4-trifluoroacetoxy-2-alkenes.