74542-78-2

Basic information

• Product Name: 5-phenyl-1-(trimethylsilyl)-1-pentyn-3-one
• Synonyms: 5-phenyl-1-(trimethylsilyl)-1-pentyn-3-one
• CAS NO: 74542-78-2
• Molecular Weight: 230.382
• Mol File: 74542-78-2.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: 5-phenyl-1-(trimethylsilyl)-1-pentyn-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-phenyl-1-(trimethylsilyl)-1-pentyn-3-one(74542-78-2)
• EPA Substance Registry System: 5-phenyl-1-(trimethylsilyl)-1-pentyn-3-one(74542-78-2)

Safety Data

• Hazardous Substances Data: 74542-78-2(Hazardous Substances Data)

Upstream product

• 622-24-2 2-phenylethyl chloride 
• 1066-54-2 trimethylsilylacetylene 
• 53210-13-2 copper(I) (trimethylsilyl)acetylide 
• 645-45-4 hydrocinnamic acid chloride 
• 104-53-0 3-phenyl-propionaldehyde 
• 54655-07-1 lithium trimethylsilylacetylenide 
• 170646-96-5 N-methoxy-N-methyl-3-phenylpropionamide 
• 501-52-0 3-Phenylpropionic acid 
• 140149-77-5 5-phenyl-1-trimethylsilylpent-1-yn-3-ol 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 17077-46-2 4-(3-phenyl-propionyl)-morpholine 

Downstream Products

• 1610944-28-9 (E)-1-(dimethyl(phenyl)silyl)-5-phenylpent-1-en-3-one 
• 1426582-68-4 (1R,2E)-1-[4-[5-phenyl-1-(trimethylsilyl)pent-2-en-1yl]phenyl]ethanone 
• 1426582-73-1 (3S,1E)-5-phenyl-1-(trimethylsilyl)pent-1-en-3-yl 2-methoxybenzoate 
• 1426582-72-0 (S,E)-5-phenyl-1-(trimethylsilyl)pent-1-en-3-ol 
• 1426582-99-1 (+)-(Z)-1-[4-(5-phenyl-3-(trifluoromethyl)pent-1-en-1yl)phenyl]ethanone 
• 1426582-95-7 (+)-(E)-1-[4-(5-phenyl-3-(trifluoromethyl)pent-1-en-1yl)phenyl]ethanone 
• 183904-26-9 (S)-5-phenyl-1-(trimethylsilyl)pent-1-yn-3-ol 
• 74542-80-6 3-Phenethyl-1-(toluene-4-sulfonyl)-5-trimethylsilanyl-1H-pyrazole 
• 74552-17-3 1-<1-(2-phenylethyl)-2-propynyl>-1-cyclohexanol 
• 74542-84-0 2-methyl-3-(2-phenylethyl)-4-pentyn-2-ol 
• 74542-81-7 trimethyl-(5-phenylpenta-1,2-dienyl)-silane 
• 119220-57-4 5-phenyl-1-trimethylsilyl-3-pentanone 
• 74542-79-3 <1-(2-phenylethyl)-3-(trimethylsilyl)-2-propynylidene>-4-methyl benzenesulfonyl hydrazide 

Relevant articles and documents

α- and γ-Regiocontrol and Enantiospecificity in the Copper-Catalyzed Substitution Reaction of Propargylic Phosphates with Grignard Reagents

The regioselectivity (r.s.) and enantiospecificity (e.s.) of the substitution reactions of secondary propargylic alcohol derivatives using reagents derived from ArMgBr and Cu salts were studied. First, the picolinate, 3-methylpicolinate, and diethylphosph

Asymmetric transfer hydrogenation of unsaturated ketones; factors influencing 1,4- vs 1,2- regio- and enantioselectivity, and alkene vs alkyne directing effects

A detailed study has been completed on the asymmetric transfer hydrogenation (ATH) of a series of enones using Ru(II) catalysts. Electron-rich rings adjacent to the C[dbnd]O group reduce the level of C[dbnd]O reduction compared to C[dbnd]C. The ATH reaction can readily discriminate between double and triple bonds adjacent to ketones, reducing the double bond but leaving a triple bond intact in the major product.

Formation of chiral C(sp3)-C(sp) bond by allylic substitution of secondary allylic picolinates and alkynyl copper reagents

(Chemical Equation Presented) To establish allylic substitution of secondary allylic alcohol derivatives with alkynyl copper reagents, allylic esters bearing the (2-pyridine)CO2-, (2-pyrazine)CO2-, (EtO)2PO2-, C6F5CO2-, o-(Ph2P)-C6H4CO2-, MeOCO 2-, or. AcO- group were examined. First, picolinate (R 1=Me, R2=CH2OPMB) was subjected to reaction with (TMS-C≡C)2CuLi 3 LiBr at 0 °C. Although no substitution took place, MgBr2 (3 equiv) was found to promote the reaction to produce the anti SN2′ product in 93% yield with 94% regioselectivity and 99% chirality transfer. In contrast, substitution of the other esters with the copper reagent in the presence of MgBr2 were less reactive ((2-pyrazine)CO2-) or marginally reactive (other cases). Generality of the substitution using picolinates was established with five picolinates (R1=Me, Ph(CH2)2, PMBO(CH 2)3; R2=Me, CH2OPMB, CH 2OTBS, C5H11, c-C6H11) and seven alkynyl copper reagents (R3=TMS, Ph, p-TBSOC 6H4, p- and o-MeOC6H4, p-MeC 6H4, p-FC6H4), furnishing anti SN2′ products in 61-93% yields with high regioselectivity (usually >90%) and high chirality transfer (usually >95%). In addition, transformation of the products was briefly studied. 2009 American Chemical Society.