72936-48-2

Basic information

• Product Name: 1-(dimethyl-t-butyl-silyloxy)-2-nitro-1-phenyl-butan
• Synonyms: 1-(dimethyl-t-butyl-silyloxy)-2-nitro-1-phenyl-butan
• CAS NO: 72936-48-2
• Molecular Weight: 309.481
• Mol File: 72936-48-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-(dimethyl-t-butyl-silyloxy)-2-nitro-1-phenyl-butan(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(dimethyl-t-butyl-silyloxy)-2-nitro-1-phenyl-butan(72936-48-2)
• EPA Substance Registry System: 1-(dimethyl-t-butyl-silyloxy)-2-nitro-1-phenyl-butan(72936-48-2)

Safety Data

• Hazardous Substances Data: 72936-48-2(Hazardous Substances Data)

Upstream product

• 7248-39-7 2-nitro-1-phenylbutyl alcohol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 100-52-7 benzaldehyde 
• 77242-14-9 (t-butyl)dimethylsilyl ester of 1-aci-nitropropane 
• 344314-52-9 (t-butyl)dimethylsilyl ester of methyl 4-aci-nitrobutanoate 

Downstream Products

• 72936-48-2 erythro-1-(t-butyl)dimethylsilyloxy-2-nitro1-phenylbutane 
• 72936-48-2 threo-1-(t-butyl)dimethylsilyloxy-2-nitro1-phenylbutane 
• 79880-94-7 1-<1'-(t-butyl)dimethylsilyloxy-1'-phenyl>methyl-propylamine 
• 72943-00-1 2-Amino-1-phenyl-butan-1-ol; compound with oxalic acid 
• 5897-76-7 2-Amino-1-phenyl-1-butanol 

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.

3-Hydroxy-4-nitro-cyclohexanones from Ketones and 4-Nitrobutanoyl Chloride. A Ring Enlarging Five-Ring Annulation

The 6-nitro-1,3-diketones 5, 8, 9, 10, and 11, prepared by a 1:1 acylation at the C-atom of non-hindered lithium enolates with 4-nitrobutanoyl chloride according to equation 3, are cyclized with sodium hydrogen carbonate in aqueous tetrahydrofuran to give the hydroxy-nitro-ketones 13-17.Such cyclic nitroaldols are not formed from the cyclopentanone, -heptanone, and -octanone, nor from the aryl derivatives 4, 6, 7 and 12, respectively.Except for the vicinally trisubstituted compound 14, the cyclization products are isolated in diastereomerically pure form.A crystal structure X-ray analysis reveals the trans-decalone and the cis-β-nitroalcohol configurations of the product 13 from cyclohexanone.Acetalization to 21-25 and catalytic hydrogenation of the nitro groups furnishes the amino alcohols 27-31 which are substrates for the Tiffeneau-Demjanow rearrangement.From the stereoelectronic control of this sextett rearrangement we deduce the configurations of the 1,4-diketones 35, 36, 39, 40, 43, 44, 46, and 47 formed under kinetic or thermodynamic conditions.The six-ring annulation with nitrobutanoic acid and the subsequent rearrangement are shown in Scheme 6; the sequence of reactions described here allows to carry out a ring enlargement of a cyclic ketone by one C-atom, with simultaneous annulation of a cyclopentanone ring.