119480-92-1

Basic information

• Product Name: (E)-3-(dimethyl(phenyl)silyl)acrylaldehyde
• Synonyms: (E)-3-(dimethyl(phenyl)silyl)acrylaldehyde
• CAS NO: 119480-92-1
• Molecular Weight: 190.317
• Mol File: 119480-92-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (E)-3-(dimethyl(phenyl)silyl)acrylaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-(dimethyl(phenyl)silyl)acrylaldehyde(119480-92-1)
• EPA Substance Registry System: (E)-3-(dimethyl(phenyl)silyl)acrylaldehyde(119480-92-1)

Safety Data

• Hazardous Substances Data: 119480-92-1(Hazardous Substances Data)

Upstream product

• 768-33-2 phenyldimethylsilyl chloride 
• 43019-63-2 3-(phenyldimethylsilyl)prop-2-yn-1-ol 
• 13247-99-9 bromo-dimethyl-phenyl-silane 
• 3839-31-4 dimethyl(phenyl)silyl lithium 
• 927-63-9 (E)-3-(dimethylamino)acrolein 
• 3839-31-4 dimethyl(phenyl)silyllithium 
• 201230-82-2 carbon monoxide 
• 766-77-8 Dimethylphenylsilane 
• 74-86-2 acetylene 
• 101844-21-7 (E)-3-[(dimethyl)phenylsilyl]prop-2-en-1-ol 

Downstream Products

• 128625-91-2 (E)-(S)-1-Benzyloxy-4-(dimethyl-phenyl-silanyl)-but-3-en-2-ol 
• 142730-67-4 (R)-(E)-(-)-1-(Dimethylphenylsilyl)-1-penten-3-ol 
• 157035-92-2 (S)-(E)-(+)-1-(Dimethylphenylsilyl)-1-penten-3-ol 
• 1296207-95-8 (1R,4R,6S)-4-(dimethyl(phenyl)silyl)-1-(hydroxymethyl)-7-phenyl-7-azabicyclo[4.1.0]heptane-3,3-dicarbonitrile 
• 1296207-86-7 (1R,4R,6S)-4-(dimethyl(phenyl)silyl)-1-formyl-7-phenyl-7-azabicyclo[4.1.0]heptane-3,3-dicarbonitrile 
• 1277185-20-2 (3R,4aS,9S,9aR)-7-bromo-3-(dimethyl(phenyl)silyl)-9-phenyl-10-(2,2,2-trifluoroacetyl)-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(9H)-dicarbonitrile 
• 1257841-91-0 (Z)-2-bromo-3-dimethylphenylsilyl-2-propenal 
• 1257842-09-3 (R)-dimethyl 2-(4-dimethylphenylsilyl-2,3-butadienyl)-2-methyl-1,3-propanedioate 
• 1257842-09-3 (S)-dimethyl 2-(4-dimethylphenylsilyl-2,3-butadienyl)-2-methyl-1,3-propanedioate 
• 1257842-09-3 dimethyl 2-(4-dimethylphenylsilyl-2,3-butadienyl)-2-methyl-1,3-propanedioate 
• 1257841-97-6 (Z)-2-bromo-1-dimethylphenylsilyl-1,3-butadiene 

Relevant articles and documents

Synthesis and Molecular Editing of Callyspongiolide, Part 1: The Alkyne Metathesis/trans-Reduction Strategy

A path-scouting investigation into the highly cytotoxic marine macrolide callyspongiolide is reported that capitalizes on the selective formation of the C10?C11 alkene site. While the closure of the macrocycle by ring closing alkyne metathesis (RCAM) with

Reactions of phenyldimethylsilyllithium with β-N,N- dimethylaminoenones: A convenient synthesis of β-dimethyl(phenyl) silylacrylic acid and its derivatives

Phenyldimethylsilyllithium reacted with 5,5-dimethyl-3-(N,N,-dimethylamino) cyclohex-2-enone (7), 3-(E)-N,N-dimethylaminopropenal (11), and 4-N,N-dimethylaminobut-3-en-2-one (13) to give the corresponding β-silyl-α,β-unsaturated carbonyl compounds 8, 12, and 14, in which the dimethylamino group has been displaced by the phenyldimethylsilyl group. Phenyldimethylsilyllithium reacted with ethyl β-N,N- dimethylaminopropenoate (15) by conjugate addition, but, in contrast to the ketones 7 and 13 and the aldehyde 11, the intermediate enolate 16 was C-protonated in the aqueous work-up to give ethyl 3-N,N-dimethylamino-3- dimethyl(phenyl)silylpropanoate (17). When the enolate 16 was instead given a mysteriously brief treatment with methyl iodide before work-up, the product was ethyl 3-(E)-dimethy(phenyl)silylpropenoate (18). Phenyllithium and methyllithium also added conjugatively to ethyl β-N,N-dimethylaminoacrylate (15) but, in contrast to the silyl case, the intermediate enolate 22 reacted unexceptionally with methyl iodide to give the products 25 and 26 of stereoselective C-methylation. This synthesis of the ester 18 was used to synthesize the Oppolzer sultam derivative 30.

Diastereoselectivity in the Preparation of β-Silyl Esters from αβ-Unsaturated Esters and Amides Attachhed to Chiral Auxiliaries

The conjugate addition of the phenyldimethylsilyl-cuprate reagent to cinnamate and crotonate esters and amides 1 of various known chiral auxiliaries, a-e, is diastereoselective.The sense of diastereoselectivity of silyl-cuprate addition to the esters 1b-d, 8 and 9 is different from established precedent based on carbon-cuprates, but is normal for silyl-cuprate addition to the amide 1a, the imines 1e and 21, and the oxazolidine 6.The chiral auxiliary e gives the best results of those tested, and the silicon-containing group can be removed from the chiral auxiliary using alkoxide ion in aprotic media, making available β-silyl esters 27-29 of high enantiomeric excess, with recovery of the chiral auxiliary 30.