119478-74-9

Basic information

• Product Name: 2-Cyclohexen-1-one, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (4S)-
• CAS NO: 119478-74-9
• Molecular Formula: C12H22O2Si
• Molecular Weight: 226.391
• Mol File: 119478-74-9.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: 2-Cyclohexen-1-one, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclohexen-1-one, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (4S)-(119478-74-9)
• EPA Substance Registry System: 2-Cyclohexen-1-one, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (4S)-(119478-74-9)

Safety Data

• Hazardous Substances Data: 119478-74-9(Hazardous Substances Data)

Upstream product

• 121652-00-4 (S)-(-)-4-hydroxy-2-cyclohexan-1-one 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 171734-48-8 tert-butyl(dimethyl)({(1S)-4-[(trimethylsilyl)oxy]cyclohex-3-en-1-yl}oxy)silane 
• 794526-34-4 (3R,4S)-3-benzylthio-4-hydroxycyclohexan-1-one 
• 77-95-2 D-(-)-quinic acid 
• 73143-44-9 (3R,4S)-3-O,4-O-cyclohexylidene-3,4-dihydroxycyclohexanone 
• 942514-50-3 (1R,4S)-4-((tert-butyldimethylsilyl)oxy)cyclohex-2-enol 
• 1215294-97-5 (2S,4S)-4-(tert-butyldimethylsilyloxy)-2-(3,4-dimethoxybenzylsulfinyl)cyclohexanone 
• 1215294-85-1 (3R,4S)-3-(3,4-dimethoxybenzylthio)-4-hydroxycyclohexanone 
• 2886-59-1 1-methoxycyclohexa-1,4-diene 
• 4096-34-8 cyclohex-3-enone 
• 85808-18-0 βγ-epoxycyclohexanone 
• 121573-17-9 (3aR,7aS)-2,2-dimethyltetrahydrobenzo[d][1,3]dioxol-5(6H)-one 
• 101917-46-8 (3aS,4R,6R,7aR)-6-Hydroxymethyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-4,6-diol 

Downstream Products

• 663169-50-4 (S)-3-[(1R,4S)-4-(tert-butyldimethylsilanoxy)-1-hydroxycyclohex-2-enyl]-1-(4-methoxybenzyloxy)azetidin-2-one 
• 663169-51-5 (R)-3-[(1S,4S)-4-(tert-butyldimethylsilanoxy)-1-hydroxycyclohex-2-enyl]-1-(4-methoxybenzyloxy)azetidin-2-one 
• 67772-76-3 (+)-5-hydroxy-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one 
• 67772-77-4 (2R,3S,4S)-2,3-Epoxy-4-hydroxy-6-methyl-5-cyclohexen-1-one 
• 532989-51-8 (2R,3S,4S)-4-tert-butyldimethylsilyloxy-2,3-epoxy-6-phenylselenylcyclohexan-1-one 
• 532989-52-9 (1R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-3-phenylselanyl-7-oxa-bicyclo[4.1.0]heptan-2-one 
• 532989-54-1 (1R,5S,6S)-3-Bromo-5-(tert-butyl-dimethyl-silanyloxy)-3-phenylselanyl-7-oxa-bicyclo[4.1.0]heptan-2-one 
• 532989-53-0 (1R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxymethyl-3-phenylselanyl-7-oxa-bicyclo[4.1.0]heptan-2-one 
• 1024596-67-5 (4S)-2-hydroxymethyl-4-O-(tert-butyldimethylsilyl)cyclohex-2-en-1-on-4-ol 
• 942514-50-3 (1R,4S)-4-((tert-butyldimethylsilyl)oxy)cyclohex-2-enol 
• 697741-23-4 (1S,4S)-4-((tert-butyldimethylsilyl)oxy)cyclohex-2-enol 
• 1020850-34-3 (4S₆R,4S₆S)-4-tert-butyldimethylsilyloxy-6-methylcyclohex-2-en-1-one 
• 473536-57-1 (4S,6R)-4-[(tert-butyldimethylsilyl)oxy]-6-methyl-2-cyclohexen-1-one 
• 1219637-06-5 C₂₂H₄₄O₂Si₃ 

Relevant articles and documents

Synthesis of Two Useful, Enantiomerically Pure Derivatives of (S)-4-Hydroxy-2-cyclohexenone

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Further study on synthesis of the cyclobakuchiols

Abstract Two results are described. First, quinic acid was transformed into the monoacetate of 2-cyclohexene-1,4-diol. The Ni-catalyzed allylic substitution of the monoacetate with CH2C(Me)MgBr/ZnCl2/TMEDA followed by oxidation of th

Temporary thio-derivatization in the synthesis of (+)-4-acetylbromoxone

A stereocontrolled synthesis of the marine natural products (+)-bromoxone (1) and (+)-4-acetylbromoxone (2) is reported. The sequence features the enzymatic kinetic resolution of 4-hydroxycyclohexenone (6) via its S-benzyl adduct. Thereafter, a base-mediated elimination-silylation generated an optically active (-)-4S-4-tert-butyldimethylsilyoxycyclohexenone (5), which then underwent diastereoselective epoxidation. Saegusa-Ito oxidation enabled formation of the corresponding α,β-unsaturated ketone 13. Bromination-elimination and subsequent removal of the silicon protecting group afforded (+)-bromoxone (1) which was converted into (+)-(4S,5R,6R)-4-acetoxy-2- bromo-5,6-epoxycyclohex-2-enone (2) [(+)-4-acetylbromoxone]. Using a luciferase gene reporter assay ED50 for NFκB inhibition of 9 μM was determined.

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.