76358-81-1

Basic information

• Product Name: tert-butyl(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)dimethylsilane
• Synonyms: tert-butyl(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)dimethylsilane
• CAS NO: 76358-81-1
• Molecular Weight: 270.531
• Mol File: 76358-81-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: tert-butyl(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)dimethylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)dimethylsilane(76358-81-1)
• EPA Substance Registry System: tert-butyl(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)dimethylsilane(76358-81-1)

Safety Data

• Hazardous Substances Data: 76358-81-1(Hazardous Substances Data)

Upstream product

• 2216-51-5 (-)-menthol 
• 29681-57-0 tert-butyldimethylsilane 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 72726-46-6 tert-butyl(dimethyl)(phenylseleno)silane 
• 753488-83-4 (1S,2R,4R)-2-(2,3-dimethylbut-2-en-1-yloxy)-1-isopropyl-4-methylcyclohexane 
• 195863-85-5 (1S,2R,4R)-1-isopropyl-4-methyl-2-(2-methylprop-2-en-1-yloxy)cyclohexane 
• 180477-54-7 (1S,2R,4R)-1-isopropyl-4-methyl-2-(3-methylbut-2-en-1-yloxy)cyclohexane 
• 72726-45-5 tert-butyldimethylsilyl iodide 

Downstream Products

• 10458-14-7 (2R,5S)-menthone 
• 61949-23-3 menthyl formate 
• 2623-23-6 L-menthyl acetate 
• 2216-51-5 (-)-menthol 

Relevant articles and documents

Dehydrogenative Silylation of Alcohols Under Pd-Nanoparticle Catalysis

Pd-nanoparticle-catalyzed dehydrogenative coupling between various hydrosilanes and alcohols was shown to provide silyl ethers in good and reproducible yields. The synthetic methodology is effective for a wide range of simple and bulky silanes and secondary alcohols, while keeping various other functional groups intact. The procedure also exhibits high selectivity for the silylation of primary versus secondary alcohols in 1,2-diols, and allows the successive silylation of alkynols and hydrogenation of the triple bond to afford Z-alkenols in good yields.

Hydromethylation of Unactivated Olefins

A solution to the classic unsolved problem of olefin hydromethylation is presented. This highly chemoselective method can tolerate labile and reactive chemical functionalities and uses a simple set of reagents. An array of olefins, including mono-, di-, and trisubstituted olefins, are all smoothly hydromethylated. This mild protocol can be used to simplify the synthesis of a specific target or to directly "edit" complex natural products and other advanced materials. The method is also amenable to the simple installation of radioactive and stable labeled methyl groups.

Allyl, methallyl, prenyl, and methylprenyl ethers as protected alcohols: Their selective cleavage with diphenyldisulfone under neutral conditions

Diphenyldisulfone is a mild and efficient reagent for selective cleavage of methylprenyl (2,3-dimethylbut-2-en-1-yl), prenyl (3-methylbut-2-en1-yl), and methallyl (2-methylallyl) ethers. These reaction conditions are compatible with the presence of other protecting groups such as acetals, acetates, and allyl, benzyl, and TBDMS ethers. Exposure of 2,3-dimethylbut-2-en-1-yl and 3-methylbut-2-en1-yl ethers to diphenyldisulfone led to the formation of 2,3-dimethylbuta-1,3-diene and isoprene, respectively. 2-Methylallyl ethers undergo isomerization to 2-methylpropenyl ethers, which are easily hydrolyzed into the corresponding free alcohols and isobutyraldehyde.