910230-21-6

Basic information

• Product Name: (R)-2-methyl-4-phenylbutane-1,2-diol
• CAS NO: 910230-21-6
• Molecular Weight: 180.247
• Mol File: 910230-21-6.mol

Chemical Properties

• CAS DataBase Reference: (R)-2-methyl-4-phenylbutane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-methyl-4-phenylbutane-1,2-diol(910230-21-6)
• EPA Substance Registry System: (R)-2-methyl-4-phenylbutane-1,2-diol(910230-21-6)

Safety Data

• Hazardous Substances Data: 910230-21-6(Hazardous Substances Data)

Upstream product

• 6683-51-8 2-methyl-4-phenyl-1-butene 
• 75074-59-8 4-phenyl-2-(hydroxymethyl)but-1-ene 
• 40692-92-0 2-methyl-4-phenyl-crotonaldehyde 
• 121517-90-6 2-methyl-4-phenyl-but-2-en-1-ol 

Downstream Products

• 910213-22-8 (R)-2-hydroxy-2-methyl-4-phenylbutyl p-toluenesulfonate 

Relevant articles and documents

Synthesis of Chiral Tertiary Boronic Esters by Oxime-Directed Catalytic Asymmetric Hydroboration

Chiral boronic esters are useful intermediates in asymmetric synthesis. We have previously shown that carbonyl-directed catalytic asymmetric hydroboration (CAHB) is an efficient approach to the synthesis of functionalized primary and secondary chiral boronic esters. We now report that the oxime-directed CAHB of alkyl-substituted methylidene and trisubstituted alkene substrates by pinacolborane (pinBH) affords oxime-containing chiral tertiary boronic esters with yields up to 87 % and enantiomeric ratios up to 96:4 e.r. The utility of the method is demonstrated by the formation of chiral diols and O-substituted hydroxylamines, the generation of quaternary carbon stereocenters through carbon-carbon coupling reactions, and the preparation of chiral 3,4,4-trisubstituted isoxazolines.

Cyanation of alcohols with diethyl cyanophosphonate and 2,6-dimethyl-1,4-benzoquinone by a new type of oxidation-reduction condensation

Cyanation of various alcohols by a new type of oxidation-reduction condensation is described. Primary alkyl diphenylphosphinites, 2,6-dimethyl-1,4-benzoquinone (DMBQ), and diethyl cyanophosphonate gave the corresponding nitriles in high yields. During the above experiment on cyanation of 4-phenylbutan-2-ol, the unexpected formation of a mixture of nitrile and isocyanide was observed. After careful examination of the reaction conditions, selective synthesis of isocyanides from secondary alcohols was successfully accomplished by the use of zinc oxide (ZnO) as an additive. Reaction of tertiary alcohols provided the corresponding isocyanides exclusively in the absence of an additive. Cyanation of optically active alcohols was tried in order to clarify the stereochemistry of this reaction, and the reaction was thus proved to proceed with the inversion of configuration.