17337-21-2

Basic information

• Product Name: 1-Phenyl-4-(trimethylsilyl)-1-butanone
• Synonyms: 1-Phenyl-4-(trimethylsilyl)-1-butanone;1-Phenyl-4-trimethylsilyl-1-butanone;SDK-31
• CAS NO: 17337-21-2
• Molecular Formula: C₁₃H₂₀OSi
• Molecular Weight: 0
• Mol File: 17337-21-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Phenyl-4-(trimethylsilyl)-1-butanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Phenyl-4-(trimethylsilyl)-1-butanone(17337-21-2)
• EPA Substance Registry System: 1-Phenyl-4-(trimethylsilyl)-1-butanone(17337-21-2)

Safety Data

• Hazardous Substances Data: 17337-21-2(Hazardous Substances Data)

Upstream product

• 36952-37-1 N-(3-methylpyridin-2-yl)-1-phenylmethanimine 
• 762-72-1 allyl-trimethyl-silane 
• 98603-79-3 (cyclopropyl(phenyl)methoxy)trimethylsilane 
• 1007-03-0 1-phenyl-1-cyclopropylmethanol 
• 104823-92-9 cyclopropyltrimethylsilylmethanone 
• 591-51-5 phenyllithium 
• 65488-05-3 4-iodobutyrophenone 
• 100-52-7 benzaldehyde 
• 3481-02-5 cyclopropyl phenyl ketone 
• 18000-27-6 trimethylsilyllithium 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 18301-86-5 γ-(trimethylsilyl)-n-butyronitrile 

Downstream Products

• 98-86-2 acetophenone 
• 495-71-6 phenacylacetophenone 
• 754-05-2 ethenyltrimethylsilane 

Relevant articles and documents

Cobalt-catalyzed intermolecular hydroacylation of olefins through chelation-assisted imidoyl C-H activation

A low-valent cobalt catalyst generated from cobalt(II) bromide, a diphosphine ligand, and zinc powder promotes intermolecular hydroacylation of olefins using N-3-picolin-2-yl aldimines as aldehyde equivalents, which affords, upon acidic hydrolysis, ketone products in moderate to good yields with high linear selectivity. The reaction is applicable to styrenes, vinylsilanes, and aliphatic olefins as well as to various aryl and heteroaryl aldimines. The cobalt catalysis features a distinctively lower reaction temperature (60 °C) compared with those required for the same type of transformations catalyzed by rhodium complexes (typically 130-150°C).

Nickel-catalyzed cross-coupling between functionalized primary or secondary alkylzinc halides and primary alkyl halides

In the presence of Bu4NI (3 equiv) and 4-fluorostyrene (20 mol %), unreactive primary and secondary alkylzinc iodides undergo nickel-catalyzed cross-couplings with various primary alkyl iodides or bromides. More reactive secondary dialkylzincs and the mixed zinc organometallics RZnTMSM undergo the cross-coupling reaction in the absence of Bu4NI. The bicyclic secondary diorganozinc 6 prepared via boron-zinc exchange reacts with high retention of configuration. Free NH-groups are tolerated in the cross-coupling allowing the synthesis of aminated products.

A Novel Mechanism for the Conversion of α-Cyclopropylbenzyl Alcohol into γ-Trimethylsilylbutyrophenone

Mechanistic studies of the reaction between α-cyclopropylbenzyl alcohol and methyl-lithium followed by hexamethyldisilane indicate that disproportionation of intermediate (4) with trimethylsilyl anion as catalyst provides cyclopropyl phenyl ketone; in situ 1,4-addition of trimethylsilyl anion to the latter compound leads to the major product, γ-trimethylsilylbutyrophenone (2).