39516-05-7

Basic information

• Product Name: (R)-4-(4′-methoxyphenyl)-2-butanol
• Synonyms: (R)-4-(4′-methoxyphenyl)-2-butanol
• CAS NO: 39516-05-7
• Molecular Weight: 180.247
• Mol File: 39516-05-7.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: (R)-4-(4′-methoxyphenyl)-2-butanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-(4′-methoxyphenyl)-2-butanol(39516-05-7)
• EPA Substance Registry System: (R)-4-(4′-methoxyphenyl)-2-butanol(39516-05-7)

Safety Data

• Hazardous Substances Data: 39516-05-7(Hazardous Substances Data)

Upstream product

• 67952-38-9 4-(4-methoxy-phenyl)-butan-2-ol 
• 108-22-5 Isopropenyl acetate 
• 1338073-32-7 3-(4-methoxyphenyl)propyl 2,4,6-triisopropylbenzoate 
• 152339-86-1 (S)-4-(4′-methoxyphenyl)-2-butanol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 104-20-1 4-(4-methoxyphenyl)-2-butanone 
• 152339-88-3 (R)-4-(p-methoxyphenyl)butan-2-ol 3,5-dinitrobenzoate 

Downstream Products

• 65982-27-6 (1R)-3-(4-hydroxyphenyl)-1-methylpropyl β-D-glucopyranoside 
• 152339-90-7 rhododendrin pentapivalate 
• 152339-92-9 (R)-4-(p-pivaloyloxyphenyl)butan-2-ol 
• 20574-98-5 4-(p-methoxyphenyl)but-1-ene 
• 18322-84-4 (E)-1-(but-2-en-1-yl)-4-methoxybenzene 
• 59092-94-3 (R)-rhododendrol 

Relevant articles and documents

Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase mutants with improved racemization activity

Controlled racemization of enantiopure alcohols is a key step in dynamic kinetic resolution. We recently reported the racemization of enantiopure phenyl-ring-containing alcohols using W110A Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase (W110A TeSADH), which relies on selectivity mistakes. Trp-110 lines the large pocket of the active site of TeSADH, which allows W110A TeSADH mutant to accommodate phenyl-ring-containing substrates in Prelog mode, albeit with selectivity mistakes. Here, we report the racemization of enantiopure phenyl-ring-containing alcohols using several Trp-110 mutants of TeSADH in the presence of the oxidized and reduced forms of nicotinamide-adenine dinucleotide. We observed a noticeable enhancement in racemization efficiency when W110G TeSADH was used compared with W110Q, W110M, W110L, W110I, and W110V. This observation was anticipated because the W110G mutation is expected to open the large pocket of the active site to a greater extent compared to other mutants of TeSADH at W110. Both enantiomers of 1-phenyl-2-propanol and 4-phenyl-2-butanol were fully racemized by W110G TeSADH. We also constructed a triple mutant of TeSADH, W110A/I86A/C295A, by site-directed mutagenesis with the aim of opening the two pockets of the active site of TeSADH. The W110A/I86A/C295A mutant was employed to racemize enantiopure phenyl-ring-containing alcohols. The current study demonstrates that W110G and W110A/I86A/C295A TeSADH are more efficient catalysts for the racemization of enantiopure secondary alcohols than the previously reported mutant W110A TeSADH [6].

Deracemization of Secondary Alcohols by using a Single Alcohol Dehydrogenase

We developed a single-enzyme-mediated two-step approach for deracemization of secondary alcohols. A single mutant of Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase enables the nonstereoselective oxidation of racemic alcohols to ketones, followed by a stereoselective reduction process. Varying the amounts of acetone and 2-propanol cosubstrates controls the stereoselectivities of the consecutive oxidation and reduction reactions, respectively. We used one enzyme to accomplish the deracemization of secondary alcohols with up to >99 % ee and >99.5 % recovery in one pot and without the need to isolate the prochiral ketone intermediate.

Synthesis of enantioenriched alkylfluorides by the fluorination of boronate complexes

The enantiospecific conversion of chiral secondary boronic esters into alkylfluorides is reported. Boronate complexes derived from boronic esters and PhLi were used as nucleophiles, with Selectfluor II as the electrophilic fluorinating agent, to afford alkylfluorides in short reaction times. The addition of styrene as a radical trap was found to enhance enantiospecificity. A broad range of alkyl boronic esters were converted into alkylfluorides with almost complete enantiospecificity by this method.