152339-86-1

Basic information

• Product Name: (S)-4-(4′-methoxyphenyl)-2-butanol
• Synonyms: (S)-4-(4′-methoxyphenyl)-2-butanol
• CAS NO: 152339-86-1
• Molecular Weight: 180.247
• Mol File: 152339-86-1.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: (S)-4-(4′-methoxyphenyl)-2-butanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-(4′-methoxyphenyl)-2-butanol(152339-86-1)
• EPA Substance Registry System: (S)-4-(4′-methoxyphenyl)-2-butanol(152339-86-1)

Safety Data

• Hazardous Substances Data: 152339-86-1(Hazardous Substances Data)

Upstream product

• 3462-97-3 (4-methoxybenzyl)triphenylphosphonium bromide 
• 5406-18-8 3-(p-methoxyphenyl)-1-propanol 
• 1338073-35-0 (S)-2-(4-(4-methoxyphenyl)butan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1338073-32-7 3-(4-methoxyphenyl)propyl 2,4,6-triisopropylbenzoate 
• 1215096-53-9 (1R,3S)-1-(4-methoxyphenyl)butane-1,3-diol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 67952-38-9 4-(4-methoxy-phenyl)-butan-2-ol 
• 104-20-1 4-(4-methoxyphenyl)-2-butanone 

Downstream Products

• 67952-38-9 4-(4-methoxy-phenyl)-butan-2-ol 
• 104-20-1 4-(4-methoxyphenyl)-2-butanone 
• 152339-92-9 (R)-4-(p-pivaloyloxyphenyl)butan-2-ol 
• 152339-87-2 (S)-4-(p-pivaloyloxyphenyl)butan-2-ol 
• 39516-05-7 (R)-4-(4′-methoxyphenyl)-2-butanol 
• 152339-89-4 epi-rhododendrin pentapivalate 
• 152339-90-7 rhododendrin pentapivalate 
• 497-78-9 (2S)-4-(4-hydroxyphenyl)but-2-yl-β-D-glucopyranoside 
• 65982-27-6 (1R)-3-(4-hydroxyphenyl)-1-methylpropyl β-D-glucopyranoside 
• 59092-94-3 (R)-rhododendrol 
• 59092-94-3 (+)-rhododendrol 
• 152339-88-3 (R)-4-(p-methoxyphenyl)butan-2-ol 3,5-dinitrobenzoate 

Relevant articles and documents

Racemization of enantiopure secondary alcohols by Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase

Controlled racemization of enantiopure phenyl-ring-containing secondary alcohols is achieved in this study using W110A secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus (W110A TeSADH) and in the presence of the reduced and oxidized forms of its cofactor nicotinamide-adenine dinucleotide. Racemization of both enantiomers of alcohols accepted by W110A TeSADH, not only with low, but also with reasonably high, enantiomeric discrimination is achieved by this method. Furthermore, the high tolerance of TeSADH to organic solvents allows TeSADH-catalyzed racemization to be conducted in media containing up to 50% (v/v) of organic solvents.

Heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis

A general and efficient method for heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis to access a wide range of structurally diverse oxygen as well as nitrogen heterocycles up to a gram scale is reported. The potential application of this new methodology is demonstrated by the total synthesis of (-)-codonopsinine and (+)-centrolobine. Herein it is proposed that selectfluor, unlike a fluorinating reagent, acts as an oxidative quencher and a hydrogen radical acceptor.

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].