130745-59-4

Basic information

• Product Name: CYCLOHEXANONE, 4-[[(1,1-DIMETHYLETHYL)DIPHENYLSILYL]OXY]-
• Synonyms: CYCLOHEXANONE, 4-[[(1,1-DIMETHYLETHYL)DIPHENYLSILYL]OXY]-;4-(tert-Butyl-diphenyl-silanyloxy)-cyclohexanone;4-[(tert-Butyl-diphenylsilyl)oxy]cyclohexanone;4-{[tert-Butyl(diphenyl)silyl]oxy}cyclohexan-1-one
• CAS NO: 130745-59-4
• Molecular Formula: C₂₂H₂₈O₂Si
• Molecular Weight: 352.547
• Mol File: 130745-59-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: CYCLOHEXANONE, 4-[[(1,1-DIMETHYLETHYL)DIPHENYLSILYL]OXY]-(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOHEXANONE, 4-[[(1,1-DIMETHYLETHYL)DIPHENYLSILYL]OXY]-(130745-59-4)
• EPA Substance Registry System: CYCLOHEXANONE, 4-[[(1,1-DIMETHYLETHYL)DIPHENYLSILYL]OXY]-(130745-59-4)

Safety Data

• Hazardous Substances Data: 130745-59-4(Hazardous Substances Data)

Upstream product

• 13482-22-9 4-hydroxycyclohexanone 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 543724-48-7 tert-butyl-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-diphenyl-silane 
• 22428-87-1 4,4-ethylenedioxycyclohexan-1-ol 
• 150-76-5 4-methoxy-phenol 
• 952589-06-9 (1R,4R)-4-((tert-butyldiphenylsilyl)oxy)cyclohexanol 
• 69125-55-9 4-hydroxy-1-methoxy-1-cyclohexene 
• 4746-97-8 cyclohexanedione monoethylene ketal 

Downstream Products

• 130745-65-2 trans-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]cyclohexanol 
• 130745-64-1 cis-4-(tert-butyl-diphenylsilyloxy)-cyclohexanol 
• 478798-39-9 methyl 5-(tert-butyldiphenylsilyloxy)-2-oxo-cyclohexan-1-carboxylate 
• 543724-50-1 4-(tert-butyldiphenylsilyloxy)cyclohex-2-enone 
• 448961-24-8 (4S)-4-t-butyldiphenylsilyloxy-2-carbomethoxycyclohexan-1-one 
• 448961-23-7 rac-4-t-butyldiphenylsilyloxy-2-carbomethoxycyclohexan-1-one 
• 951386-29-1 2-isopropylidene-4-(tert-butyldiphenylsilyloxy)cyclohexanone 
• 543724-51-2 2-bromo-4-(tert-butyl-diphenyl-silanyloxy)-cyclohex-2-enone 
• 543724-54-5 (3-bromo-4-hept-6-enylidene-cyclohex-2-enyloxy)-tert-butyl-diphenyl-silane 
• 543724-55-6 3-(tert-butyl-diphenyl-silanyloxy)-6-hept-6-enylidene-cyclohex-1-enecarbaldehyde 

Relevant articles and documents

GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with a defect in glyoxylate metabolism, for example a disease or disorder associated with the enzyme glycolate oxidase (GO) or alterations in oxalate metabolism. Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.

GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme glycolate oxidase (GO). Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.

Oxidation of alcohols to aldehydes or ketones with 1-acetoxy-1,2- benziodoxole-3(1H)-one derivatives

Various benzylic and aliphatic alcohols were smoothly oxidized to the corresponding aromatic aldehydes and ketones as well as aliphatic ketones by treatment with 1-acetoxy-5-nitro-1,2-benziodoxole-3(1H)-one (ANBX), 1-acetoxy-5-bromo-1,2-benziodoxole-3(1H)-one (ABBX), 1-acetoxy-5-chloro-1,2- benziodoxole-3(1H)-one (ACBX), and 1-acetoxy-5-fluoro-1,2-benziodoxole-3(1H)-one (AFBX). These new tri-valent iodine compounds were prepared from 5-substituted 2-iodobenzoic acids and meta-chloroperoxybenzoic acid (m-CPBA). ANBX and ABBX were the most effective reagents for this oxidation of alcohols, and this present reaction is very attractive because of the ease of product isolation and the reusability of the reagents.

Oxidation of Alcohols to Aldehydes or Ketones with 1-Acetoxy-1,2-benziodoxole-3(1H)-one Derivatives

Various benzylic and aliphatic alcohols were smoothly oxidized to the corresponding aromatic aldehydes and ketones as well as aliphatic ketones by treatment with 1-acetoxy-5-nitro-1,2-benziodoxole-3(1H)-one (ANBX), 1-acetoxy-5-bromo-1,2-benziodoxole-3(1H)-one (ABBX), 1-acetoxy-5-chloro-1,2-benziodoxole-3(1H)-one (ACBX), and 1-acetoxy-5-fluoro-1,2-benziodoxole-3(1H)-one (AFBX). These new trivalent iodine compounds were prepared from 5-substituted 2-iodobenzoic acids and meta-chloroperoxybenzoic acid (m-CPBA). ANBX and ABBX were the most effective reagents for this oxidation of alcohols, and this present reaction is very attractive because of the ease of product isolation and the reusability of the reagents.

2-iodoxybenzenesulfonic acid as an extremely active catalyst for the selective oxidation of alcohols to aldehydes, ketones, carboxylic acids, and enones with oxone

Electron-donating group-substituted 2-iodoxybenzoic acids (IBXs) such as5-Me-IBX (1g), 5-MeO-IBX (1h), and 4,5-Me2-IBX were superior to IBX 1a as catalysts for the oxidation of alcohols with Oxone (a trad emark of DuPont) under nonaqueous conditions, although Oxone was almost insoluble in most organic solvents. The catalytic oxidation proceeded more rapidly and cleanly in nitromethane. Furthermore, 2-iodoxybenzenesulfonic acid (IBS, 6a) was much more active than modified IBXs. Thus, we established a highly efficient and selective method for the oxidation of primary and secondary alcohols to carbonyl compounds such as aldehydes, carboxylic acids, and ketones with Oxone in nonaqueous nitromethane, acetonitrile, or ethyl acetate in the presence of 0.05-5molpercentof 6a, which was generated in situ from 2-iodobenzenesulfonic acid (7a) or its sodium salt. Cycloalkanones could be further oxidized to α,β- cycloalkenones or lactones by controlling the amounts of Oxone under the same conditions as above. When Oxone was used under nonaqueous conditions, Oxone wastes could be removed by simple filtration. Based on theoretical calculations, we considered that the relatively ionic character of the intramolecular hypervalent iodine-OSO2 bond of IBS might lower the twisting barrier of the alkoxyperiodinane intermediate 16.

A diene-transmissive approach to the quassinoid skeleton

Several tetracyclic molecules were prepared by diene-transmissive Diels-Alder cycloadditions. Control over the stereochemical outcome of the cycloaddition was achieved and the structural features of the precursors affecting the stereochemistry is discussed. Useful information was gathered concerning the factors governing this stereocontrol, which will be indispensable for the future of this strategy.

Enantioselective deprotonation of protected 4-hydroxycyclohexanones

A series of derivatives of 4-hydroxycyclohexanone (1a-g) with the hydroxy group protected as a silyl ether (1a,b), ether (1d,g), an acetal (1c), or an ester (1e,f) were deprotonated with chiral, optically pure, lithium amides 3-9. The resulting non-racemic enolates were trapped as enol acetates. The enantioselectivity of deprotonation was up to 74percent ee.

Thermal -Sigmatropic Shift of Previtamin D3 to Vitamin D3: Synthesis and Study of Pentadeuterio Derivatives

Specifically pentadeuteriated previtamin D3 11 has been synthesized to impart thermal stability to the otherwise labile material.A 12-step synthesis of the trideuteriated A-ring 14b from p-methoxyphenol was developed and employed the addition of (methyl-d3)magnesium iodide to either the keto thiomethylene intermediate 23 or the keto dioxane 27.The enantiomerically pure trideuterio A-ring (-)-14b was then coupled with the deuteriated CD fragment 13b followed by hydrogenation to afford pentadeuteriated previtamin D3 11.A primary deuterium kinetic isotope effect (KIE) study of the -sigmatropic hydrogen migration in the conversion of previtamin D3 to vitamin D3 indicated a more "normal" primary deuterium isotope effect (as compared to a previously reported literature value of ca. 45).At 80 deg C, a kH/kD for the previtamin D3 to vitamin D3 isomerization was determined to be ca. 6.2.At 25 deg C, this -sigmatropic hydrogen migration proceeds with a kH/kD of ca. 11.4.The revisible, first-order -sigmatropic hydrogen shift of previtamin D3 to D3, determined over the temperature range 60.1-85.5 deg C is characterized by the following activation parameters: log AH = 8.8 and EaH = 19.6 kcal/mol.Deuteriated pre-D3, which rearranges over this temperature range, is characterized by the activation parameters log AD = 9.5 and EaD = 21.9 kcal/mol.