139278-54-9

Basic information

• Product Name: Silane, [(1-methylene-2-propenyl)oxy]tris(1-methylethyl)-
• CAS NO: 139278-54-9
• Molecular Formula: C13H26OSi
• Molecular Weight: 226.434
• Mol File: 139278-54-9.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Silane, [(1-methylene-2-propenyl)oxy]tris(1-methylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, [(1-methylene-2-propenyl)oxy]tris(1-methylethyl)-(139278-54-9)
• EPA Substance Registry System: Silane, [(1-methylene-2-propenyl)oxy]tris(1-methylethyl)-(139278-54-9)

Safety Data

• Hazardous Substances Data: 139278-54-9(Hazardous Substances Data)

Upstream product

• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 
• 78-94-4 methyl vinyl ketone 

Downstream Products

• 33553-25-2 2-(2-oxopropyl)cyclohex-2-en-1-one 
• 162733-38-2 ((R)-3-Methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-((S)-1-methyl-4-triisopropylsilanyloxy-cyclohex-3-enyl)-methanone 
• 139278-40-3 (1S,4R)-4,7,7-Trimethyl-2-(1-methyl-4-triisopropylsilanyloxy-cyclohex-3-enecarbonyl)-2-aza-bicyclo[2.2.1]heptan-3-one 

Relevant articles and documents

Asymmetric Diels-Alder Reactions of Chiral N-Methacryloylsultams with 1,3-Dienes

R2AlCl-coordinated N-methacryloylsultam 1c undergoes efficient, endo-selective and highly diastereoface controlled -additions to cyclopentadiene, isoprene, (E)-piperylene and the 2-silyloxydienes 10 and 12.The resulting cystalline cycloadducts are smoothly reduced with LiAlH4 providing the recovered auxiliary and the corresponding enentiomerically pure alcohols.

Concise total syntheses of palominol, dolabellatrienone, β-araneosene, and isoedunol via an enantioselective Diels-Alder macrobicyclization

Concise total syntheses of four members of the dolabellane family of diterpenoid natural products are reported. Key features of the developed route include the first demonstration of an enantioselective, intramolecular Type I Diels-Alder macrobicyclization, the first example of a stereoselective π-allyl Stille coupling reaction involving a farnesyl-derived intermediate, a powerful new reagent for the formation of dithianes with acid-sensitive molecules, and a unique and highly efficient ring-contraction sequence based on a modified Wolff photochemical rearrangement. Copyright

Regio- and stereoselective nickel-catalyzed homoallylation of aldehydes with 1,3-dienes

Ni(acac)2 catalyzes homoallylation of aldehydes with 1,3-dienes in the presence of triethylborane. Triethylborane serves as a reducing agent delivering a formal hydride to the C2 position of 1,3-dienes, thus generating a formal homoallyl anion species and enabling the novel homoallylation of aldehydes. The reaction proceeds smoothly at room temperature in the absence of any phosphane or nitrogen ligands and is highly regioselective and stereoselective for a wide variety combination of aldehydes and 1,3-dienes: e.g., isoprene and benzaldehyde combine to give a mixture of anti- and syn-1-phenyl-3-methyl-4-penten-1-ol (2.2) in a ratio of 15:1 in 90% yield. Under the conditions, sterically congested aliphatic aldehydes and ketones show low yields. In such cases, diethylzinc serves as a substitute for triethylborane and yields the expected products in good yields with similarly high regio- and stereoselectivity. 1,3-Cyclohexadiene is one exception among 24 kinds of dienes examined and undergoes allylation (not homoallylation) selectively.