138663-83-9

Basic information

• Product Name: Silane, [(3-cyclohexyloxiranyl)ethynyl]trimethyl-, cis-
• CAS NO: 138663-83-9
• Molecular Formula: C13H22OSi
• Molecular Weight: 222.403
• Mol File: 138663-83-9.mol

Chemical Properties

• CAS DataBase Reference: Silane, [(3-cyclohexyloxiranyl)ethynyl]trimethyl-, cis-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, [(3-cyclohexyloxiranyl)ethynyl]trimethyl-, cis-(138663-83-9)
• EPA Substance Registry System: Silane, [(3-cyclohexyloxiranyl)ethynyl]trimethyl-, cis-(138663-83-9)

Safety Data

• Hazardous Substances Data: 138663-83-9(Hazardous Substances Data)

Upstream product

• 38002-45-8 3-bromo-1-(trimethylsilyl)-1-propyne 
• 143798-87-2 3-trimethylsilylprop-2-ynyldiisobutyltelluronium bromide 
• 2043-61-0 cyclohexanecarbaldehyde 
• 42134-57-6 (Z)-4-cyclohexyl-1-trimethylsilyl-3-buten-1-yne 

Downstream Products

• 79015-64-8 (S)-1-Cyclohexyl-4-trimethylsilanyl-but-3-yn-1-ol 

Relevant articles and documents

Enantioselective Epoxidation of Conjugated Dienes and Enynes. Trans-Epoxides from cis-Olefins

Asymmetric epoxidation of conjugated dienes and enynes catalyzed by (salen)Mn(II) coplex I takes place with high chemoselectivity to afford monoepoxides exclusively.Reactions of cis-enynes proceed with very high levels of asymmetric induction, with trans-alkynyl epoxides as the major products.

Reactions of Carbonyl Compounds with diisobutyltelluronium Bromide Mediated by Different Strong Bases: Highly Regioselective Synthesis of (Trimethylsilyl)propargyl Alcohol and Highly Stereoselective Synthesis of cis-(Trimethylsilyl)alkynyl Epoxides

diisobutyltelluronium bromide (1), after being treated with alkyl- or aryllithium reagent, undergoes a lithium-tellurium exchange reaction via an unstable transient tetraorganyltellurium intermediate, and the in situ generated lithium species react with carbonyl compounds to give (trimethylsilyl)propargyl alcohols 2 in high yields with high regioselectivity.However, when the telluronium salt 1 was treated with nonnucleophilic bases such as LDA or lithium 2,2,6,6-tetramethylpiperidide, the moderately stabilized silylated telluronium ylide formed.The silylated telluronium ylide reacted with carbonyl compounds to afford (trimethylsilyl)alkynyl epoxides 11 in good to excellent yields with high cis stereoselectivity.

Facile and Highly Stereoselective Synthesis of cis-Trimethylsilylethynyl Epoxides via a Silylated Telluronium Ylide

Diisobutyltelluronium trimethylsilylpropynyl ylide, generated from 3-trimethylsilylprop-2-ynyldiisobutyltelluronium bromide with lithium 2,2,6,6-tetramethylpiperidide (LiTMP), reacts with carbonyl compounds to afford predominately cis-trimethylsilylethynyl epoxides in good to excellent yields.