77130-15-5

Basic information

• Product Name: Silane, trimethyl(2-phenyl-2-propenyl)-
• CAS NO: 77130-15-5
• Molecular Formula: C12H18Si
• Molecular Weight: 190.36
• Mol File: 77130-15-5.mol
• Article Data: 32

Chemical Properties

• CAS DataBase Reference: Silane, trimethyl(2-phenyl-2-propenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, trimethyl(2-phenyl-2-propenyl)-(77130-15-5)
• EPA Substance Registry System: Silane, trimethyl(2-phenyl-2-propenyl)-(77130-15-5)

Safety Data

• Hazardous Substances Data: 77130-15-5(Hazardous Substances Data)

Upstream product

• 93-58-3 benzoic acid methyl ester 
• 13170-43-9 (trimethylsilyl)methylmagnesium chloride 
• 917-64-6 methyl magnesium iodide 
• 139214-53-2 2-phenyl-2-(trimethylsilylmethyl)-1,3-dithiane 
• 108-86-1 bromobenzene 
• 135112-59-3 C₁₄H₃₅BOSi₃ 
• 125405-22-3 2-trimethylstannyl-3-trimethylsilylpropene 
• 591-50-4 iodobenzene 
• 762-72-1 allyl-trimethyl-silane 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 75-77-4 chloro-trimethyl-silane 
• 36963-72-1 (3-phenoxyprop-1-en-2-yl)benzene 
• 1822-00-0 trimethylsilylmethyllithium 
• 126300-69-4 Bis-trimethylsilanylmethyl-(1-trimethylsilanylmethyl-vinyl)-borane 

Downstream Products

• 144650-21-5 C₁₉H₂₀S 
• 144650-05-5 C₂₆H₂₆S 
• 144650-27-1 C₂₀H₂₂S 
• 58541-15-4 trans-1-(trimethylsilyl)-3-phenyl-1-propene 
• 98-83-9 isopropenylbenzene 
• 125315-74-4 2-(2-Phenyl-allyl)-succinic acid dimethyl ester 
• 14584-33-9 2,2,2-trifluoro-1-phenylethan-1-one 
• 104798-41-6 (4,4,4-trifluorobut-1-en-2-yl)benzene 
• 1380233-06-6 5-(4,4,4-trifluorobut-1-en-2-yl)benzo[d][1,3]dioxole 
• 1380233-12-4 C₁₀H₉F₃O 
• 1380233-14-6 [3-(trifluoromethyl)hept-1-en-2-yl]benzene 
• 1380233-16-8 (Z)-trifluoromethylated 2-phenyl allylic alcohol 
• 89619-30-7 (E)-2-phenyl-4,4,4-trifluorobut-2-en-1-ol 
• 140156-00-9 1-methyl-4-(2-phenylallyl)benzene 

Relevant articles and documents

Enantioselective, Catalytic Multicomponent Synthesis of Homoallylic Amines Enabled by Hydrogen-Bonding and Dispersive Interactions

We report a one-step catalytic, enantioselective method for the preparation of homoallylic N-Boc amines directly from acetals. Reactive iminium ion intermediates are generated in situ through the combination of an acetal, a chiral thiourea catalyst, trialkylsilyl triflate, and N-Boc carbamate and are subsequently trapped by a variety of allylsilane nucleophiles. No homoallylic ether byproducts are detected, consistent with allylation of the iminium intermediate being highly favored over allylation of the intermediate oxocarbenium ion. Acetals derived from aromatic aldehydes possessing a variety of functional groups and substitution patterns yield homoallylic amines with excellent levels of enantiomeric enrichment. Experimental and computational data are consistent with an anchoring hydrogen-bond interaction between the protioiminium ion and the amide of the catalyst in the enantiodetermining transition state, and with stereodifferentiation achieved through specific noncovalent interactions (NCIs) with the catalyst pyrenyl moiety. Evidence is provided that the key NCI in the major pathway is a π-stacking interaction, contrasting with the cation-πinteractions invoked in previously studied reactions promoted by the same family of aryl-pyrrolidino-H-bond-donor catalysts.

Enantioselective Synthesis of α-Allyl Amino Esters via Hydrogen-Bond-Donor Catalysis

We report a chiral-squaramide-catalyzed enantio- and diastereoselective synthesis of α-allyl amino esters. The optimized protocol provides access to N-carbamoyl-protected amino esters via nucleophilic allylation of readily accessible α-chloro glycinates. A variety of useful α-allyl amino esters were prepared, including crotylated products bearing vicinal stereocenters that are inaccessible through enolate alkylation, with high enantioselectivity (up to 97% ee) and diastereoselectivity (>10:1). The reactions display first-order kinetic dependence on both the α-chloro glycinate and the nucleophile, consistent with rate-limiting C-C bond formation. Computational analysis of the uncatalyzed reaction predicts an energetically inaccessible iminium intermediate, and a lower energy concerted SN2 mechanism.

Silver-promoted cross-coupling of substituted allyl(trimethyl)silanes with aryl iodides by palladium catalysis

A ligand-free Pd-catalyzed cross-coupling of substituted allyl(trimethyl)silanes with aryl iodides enabled by silver salts was developed. This reaction delivered allylic arenes chemoselectively and regioselectively. The study suggested that the reaction might proceed through oxidative addition of ArI to Pd(0) followed by halide abstraction to give an electrophilic complex ArPdX, which further reacted with allyl(trimethyl)silanes via electrophilic addition/desilylation/reductive elimination to afford the allyl-aryl coupling products.