78805-31-9

Basic information

• Product Name: (R)-2-methyl-3-phenyl-butane-2,3-diol
• Synonyms: (R)-2-methyl-3-phenyl-butane-2,3-diol
• CAS NO: 78805-31-9
• Molecular Weight: 180.247
• Mol File: 78805-31-9.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (R)-2-methyl-3-phenyl-butane-2,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-methyl-3-phenyl-butane-2,3-diol(78805-31-9)
• EPA Substance Registry System: (R)-2-methyl-3-phenyl-butane-2,3-diol(78805-31-9)

Safety Data

• Hazardous Substances Data: 78805-31-9(Hazardous Substances Data)

Upstream product

• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 917-64-6 methyl magnesium iodide 
• 60-29-7 diethyl ether 
• 2406-23-7 atrolactic acid ethyl ester 
• 769-57-3 α,β,β-trimethylstyrene 
• 201230-82-2 carbon monoxide 
• 98-86-2 acetophenone 
• 917-54-4 methyllithium 
• 78805-21-7 (S)--2-(methoxymethyl)pyrrolidine 
• 67-64-1 acetone 
• 21578-99-4 rac-α,β,β-trimethylstyrene oxide 
• 75-16-1 methylmagnesium bromide 
• 579-07-7 1-Phenylpropane-1,2-dione 

Downstream Products

• 18476-73-8 (3-methylbuta-1,3-dien-2-yl)benzene 
• 96418-46-1 Schwefligsaeure-(trimethyl-phenyl-ethylenester) 
• 98-86-2 acetophenone 
• 78592-15-1 3-methyl-4-phenyl-3-sulfolene 
• 108475-84-9 (+/-)-4-methyl-5-phenyl-cyclohex-4-ene-1r,2c-dicarboxylic acid-anhydride 
• 178313-67-2 2-methyl[1,1'-biphenyl]-4-carboxylic acid 
• 855406-10-9 4-methyl-5-phenyl-cyclohexa-1,4-dienecarboxylic acid 
• 856184-69-5 5-methyl-4-phenyl-cyclohexa-1,4-dienecarboxylic acid 
• 855408-55-8 4-methyl-5-phenyl-cyclohexa-1,4-diene-1,2-dicarboxylic acid 
• 855408-54-7 4-methyl-5-phenyl-cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester 
• 2977-35-7 2,3-Dimethyl-3-phenyl-1-butanol 
• 2977-36-8 3,4-Dimethyl-4-phenylvaleriansaeure 
• 770-85-4 2-methyl-2-phenylbutan-3-one 

Relevant articles and documents

Lewis Acid Assisted Electrophilic Fluorine-Catalyzed Pinacol Rearrangement of Hydrobenzoin Substrates: One-Pot Synthesis of (±)-Latifine and (±)-Cherylline

A microwave-irradiated solvent-free pinacol rearrangement of hydrobenzoin substrates catalyzed by a combination of N-fluorobenzenesulfonimide and FeCl3·6H2O was developed. Its selectivity was first investigated by density functional theory (DFT) calculations. Then the functional group tolerance was examined by synthesizing a series of substrates designed based on the insight provided by the DFT calculations. The application of the methodology was demonstrated by the efficient one-pot synthesis of (±)-latifine and (±)-cherylline, both are 4-aryltetrahydroisoquinoline alkaloids isolated from Amaryllidacecae plants.

Unexpected TiIII/Mn-promoted pinacol coupling of ketones

Titanocene(III) chemistry has emerged in the last decades as an indispensable tool in C-C bond-forming reactions. In this context, pinacol and related reactions allow the stereoselective synthesis of vicinal diols. In this work, we present new applications of these reactions using as starting materials aromatic ketones. Simple and smooth reaction conditions have been developed and have been applied for inter- and intramolecular processes. We also describe that although Cp2TiCl is usually used as a monoelectronic reducing agent, it can be also used as an efficient Lewis acid.

Mg-promoted mixed pinacol coupling

Mg-promoted reduction of a mixture of aromatic ketones (or imines) and aliphatic carbonyl compounds in N,N-dimethylformamide (DMF) brought about unique mixed pinacol type of cross coupling to give unsymmetrical vicinal diols (or amino alcohols) or α-hydroxyketones in good to moderate yields. The reaction may be initiated by electron transfer from magnesium metal to an aromatic carbonyl compound possessing a less negative reduction potential. The difference of reduction potential between aromatic ketones (or imines) and aliphatic carbonyl compounds was found to be one of the important key factors in this selective cross coupling.