163799-44-8

Basic information

• Product Name: 1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-phenyl-2-propanone
• Synonyms: 1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-phenyl-2-propanone
• CAS NO: 163799-44-8
• Molecular Weight: 264.44
• Mol File: 163799-44-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-phenyl-2-propanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-phenyl-2-propanone(163799-44-8)
• EPA Substance Registry System: 1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-phenyl-2-propanone(163799-44-8)

Safety Data

• Hazardous Substances Data: 163799-44-8(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 164853-29-6 (±)-methyl 2-{[(tert-butyldimethylsilyl)oxy](phenyl)methyl}prop-2-enoate 
• 18020-59-2 methyl 3-hydroxy-2-methylidene-3-phenylpropionate 
• 1038432-29-9 (+/-)-2-{[(tert-butyldimethylsilyl)oxy](phenyl)methyl}prop-2-enoic acid 
• 83205-07-6 1-tert-butyldimethylsilyloxy-1-phenyl-2-methylprop-2-ene 
• 90-63-1 (RS)-1-hydroxy-1-phenylpropan-2-one 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 189072-85-3 (3R,4S)-3-[(1R)-1-tert-butyldimethylsiloxyethyl]-4-(3-tert-butyldimethylsiloxy-3-phenyl-2-oxopropyl)azetidin-2-one 
• 90-63-1 (RS)-1-hydroxy-1-phenylpropan-2-one 
• 182196-52-7 [1-(tert-Butyl-dimethyl-silanyloxy)-2-trimethylsilanyloxy-allyl]-benzene 
• 1855-09-0 1-phenyl-1,2-propandiol 

Relevant articles and documents

Sequential Reduction of Nitroalkanes Mediated by CS2 and Amidine/Guanidine Bases: A Controllable Nef Reaction

In this letter, we describe a mild, functional group-tolerant reductive Nef reaction that utilizes CS2 and an amidine or guanidine base to sequentially cleave N-O bonds. These conditions transform secondary nitroalkanes to ketones via an isolable oxime with minimal erosion at labile stereogenic carbons, show excellent compatibility with groups sensitive to oxidizing or reducing conditions, display good scalability, and are well-suited for generating useful 3-pyrrolidinone motifs from readily accessible 1,3-dipolar cycloaddition products.

A convenient and versatile method for the preparation of α-hydroxymethyl ketone derivatives from the corresponding allyl silyl ethers or allyl carboxylates

The ozonolysis of 1-substituted allyl silyl ethers or 1-substituted allyl carboxylates followed by treatment with bases gave the corresponding α-silyloxymethyl- or α-acyloxymethyl-ketones in good yields. It is proposed to proceed via the corresponding α-silyloxy- or α-acyloxyaldehydes intermediates followed by 1,4-group migration. The results of theoretical calculations are applicable to explain the experimental results.

Reversal of the facial diastereoselectivity in the Paterno-Buchi reaction of silyl enol ethers carrying a chiral substituent in α-position

The facial diastereoselectivity in the Paterno-Buchi reaction of benzaldehyde and silyl enol ethers 1 which bear a chiral substituent R* in α-position has been studied. Since the regioselectivity and the simple diastereoselectivity of the photocycloaddition is very good only two diastereoisomers are obtained whose ratio reflects the facial diastereoselectivity. With the silyloxy substituted substrates 1a-1c the selectivity is low (d.r. = 60/40). The benzyloxy substituted silyl enol ether 1d (R* = CHOBni-Pr), however, exhibits already a significant degree of diastereofacial selection and yields preferentially the oxetane 2d (d.r. = 67/33). If the benzyloxy substituent in the substrate is replaced by a chlorine atom (R* = CHCli-Pr) the direction of the facial diastereoselectivity is reverted. Thus, the reaction of silyl enol ether 1e with benzaldehyde gives preferentially oxetane 3e (d.r. = 85/115).