(S)-4-(4′-methoxyphenyl)-2-butanol | 152339-86-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-4-(4′-methoxyphenyl)-2-butanol
• 英文别名: (S)-4-(4'-methoxyphenyl)-2-butanol；(S)-4-(4'-methoxyphenyl)butan-2-ol；(S)-4-(4-methoxyphenyl)-2-butanol；(S)-4-(4-methoxyphenyl)butan-2-ol；(S)-4-(p-methoxyphenyl)butan-2-ol；(2S)-4-(4-methoxyphenyl)butan-2-ol
• CAS: 152339-86-1
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: UOACSUDCGMMDFW-VIFPVBQESA-N

物化性质

• 沸点：
  292.6±15.0 °C(Predicted)
• 密度：
  1.017±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-4-(4′-methoxyphenyl)-2-butanol 在 sodium tetrahydroborate 、 NADPH 、 nicotinamide adenine dinucleotide phosphate 、 W₁₁₀G TeSADH 作用下， 以 乙腈 为溶剂， 生成 4-(4-甲氧基苯基)丁烷-2-醇
  参考文献：
  名称：

  Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase mutants with improved racemization activity

  摘要：

  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/186A/C295A, by site-directed mutagenesis with the aim of opening the two pockets of the active site of TeSADH. The W110A/186A/C295A mutant was employed to racemize enantiopure phenyl-ring-containing alcohols. The current study demonstrates that W110G and W110A/186A/C295A TeSADH are more efficient catalysts for the racemization of enantiopure secondary alcohols than the previously reported mutant W110A TeSADH [6]. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2015.02.012
• 作为产物：
  描述：

  4-(4-甲氧基苯基)丁烷-2-醇 在 Thermoanaerobacter ethanolicus (W₁₁₀A TESADH) 、 nicotinamide adenine dinucleotide phosphate tris-buffer 、 Thermoanaerobacter ethanolicus (W₁₁₀A TESADH) 、 nicotinamide adenine dinucleotide phosphate 、 异丙醇 、 丙酮 作用下， 以 水 为溶剂， 反应 20.0h， 生成 (S)-4-(4′-methoxyphenyl)-2-butanol
  参考文献：
  名称：

  不对称还原和芳香酮的氧化和醇使用W110A的次级醇脱氢酶嗜热ethanolicus

  摘要：

  使用2-丙醇（30％，v / v）作为助溶剂，在Tris缓冲液中用乙醇热嗜热厌氧菌（W110A TESADH）的W110A仲醇脱氢酶实现对苯环前手性酮的对映选择性的不对称还原，得到相应的旋光性仲醇。和共同基板。2-丙醇的这种浓度不仅对于提高含疏水性苯环的底物在水性反应介质中的溶解度至关重要，而且对于在还原方向上移动平衡也是至关重要的。将所得的醇具有小号-构型，在具有普雷洛格的规则，其中，所述烟酰胺腺嘌呤二核苷酸磷酸（NADPH）辅因子传送其协议亲-R氢化物的重面对酮。还原了一系列含苯环的酮，例如4-苯基-2-丁酮（1a）和1-苯基-1,3-丁二酮（2a），具有良好的产率和优异的对映选择性。另一方面，ee比2-丁酮衍生物低，因此1-苯基-2-丙酮（7a）被还原。（R）醇是抗Prelog产物，是通过在Tris缓冲液/丙酮（90:10，v / v）中使用W110A TESADH通过外消旋醇的氧化

  DOI：

  10.1021/jo0616097

文献信息

• Deracemization of Secondary Alcohols by using a Single Alcohol Dehydrogenase
  作者：Ibrahim Karume、Masateru Takahashi、Samir M. Hamdan、Musa M. Musa

  DOI：10.1002/cctc.201600160

  日期：2016.4.20

  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

  我们开发了一种单酶介导的两步法来对仲醇进行脱脂。乙醇嗜热厌氧菌仲醇脱氢酶的单个突变体能够使外消旋醇非立体选择性氧化为酮，然后进行立体选择性还原过程。改变丙酮和2-丙醇共底物的量分别控制连续氧化和还原反应的立体选择性。我们使用一种酶完成了仲醇的脱硝作用，一锅中的ee高达99％以上，回收率达到99.5％以上，而无需分离前手性酮中间体。
• Activity and selectivity of W110A secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus in organic solvents and ionic liquids: mono- and biphasic media
  作者：Musa M. Musa、Karla I. Ziegelmann-Fjeld、Claire Vieille、Robert S. Phillips

  DOI：10.1039/b717120j

  日期：——

  The asymmetric reduction of hydrophobic phenyl-ring-containing ketones and the enantiospecific kinetic resolution of the corresponding racemic alcohols catalyzed by Thermoanaerobacter ethanolicus W110A secondary alcohol dehydrogenase were performed in mono- and biphasic systems containing either organic solvents or ionic liquids. Both yield and enantioselectivity for these transformations can be controlled

  在含有有机溶剂或离子液体的单相和双相体系中，进行了乙醇热嗜热菌W110A仲醇脱氢酶催化的疏水性含苯环的酮的不对称还原和相应外消旋醇的对映体动力学拆分。这些转化的产率和对映选择性都可以通过改变反应介质来控制。该酶对与水混溶和与水混溶的溶剂均显示出很高的耐受性，从而可以在高底物浓度下进行生物转化。
• Racemization of enantiopure secondary alcohols by Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase
  作者：Musa M. Musa、Robert S. Phillips、Maris Laivenieks、Claire Vieille、Masateru Takahashi、Samir M. Hamdan

  DOI：10.1039/c3ob27415b

  日期：——

  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

  在这项研究中，使用乙醇嗜热厌氧菌的W110A仲醇脱氢酶（W110A TeSADH）并在其辅因子烟酰胺-腺嘌呤二核苷酸的还原和氧化形式下，实现了对映体纯的含苯环的仲醇的受控外消旋作用。W110A TeSADH接受的两种醇的对映异构体的外消旋化，不仅对映异构体歧视程度低，而且合理地对映异构体歧视程度也很高。此外，TeSADH对有机溶剂的高度耐受性使TeSADH催化的消旋作用可以在含有高达50％（v / v）的有机溶剂的介质中进行。
• Asymmetric Reduction and Oxidation of Aromatic Ketones and Alcohols Using W110A Secondary Alcohol Dehydrogenase from <i>Thermoanaerobacter </i><i>ethanolicus</i>
  作者：Musa、Karla I. Ziegelmann-Fjeld、Claire Vieille、J. Gregory Zeikus、Robert S. Phillips

  DOI：10.1021/jo0616097

  日期：2007.1.1

  An enantioselective asymmetric reduction of phenyl ring-containing prochiral ketones to yield the corresponding optically active secondary alcohols was achieved with W110A secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus (W110A TESADH) in Tris buffer using 2-propanol (30%, v/v) as cosolvent and cosubstrate. This concentration of 2-propanol was crucial not only to enhance the solubility

  使用2-丙醇（30％，v / v）作为助溶剂，在Tris缓冲液中用乙醇热嗜热厌氧菌（W110A TESADH）的W110A仲醇脱氢酶实现对苯环前手性酮的对映选择性的不对称还原，得到相应的旋光性仲醇。和共同基板。2-丙醇的这种浓度不仅对于提高含疏水性苯环的底物在水性反应介质中的溶解度至关重要，而且对于在还原方向上移动平衡也是至关重要的。将所得的醇具有小号-构型，在具有普雷洛格的规则，其中，所述烟酰胺腺嘌呤二核苷酸磷酸（NADPH）辅因子传送其协议亲-R氢化物的重面对酮。还原了一系列含苯环的酮，例如4-苯基-2-丁酮（1a）和1-苯基-1,3-丁二酮（2a），具有良好的产率和优异的对映选择性。另一方面，ee比2-丁酮衍生物低，因此1-苯基-2-丙酮（7a）被还原。（R）醇是抗Prelog产物，是通过在Tris缓冲液/丙酮（90:10，v / v）中使用W110A TESADH通过外消旋醇的氧化
• Expanding the Substrate Specificity of <i>Thermoanaerobacter pseudoethanolicus</i> Secondary Alcohol Dehydrogenase by a Dual Site Mutation
  作者：Musa M. Musa、Odey Bsharat、Ibrahim Karume、Claire Vieille、Masateru Takahashi、Samir M. Hamdan

  DOI：10.1002/ejoc.201701351

  日期：2018.2.14

  The authors acknowledge the support provided by the Deanship of Scientific Research (DSR) at King Fahd University of Petroleum and Minerals (KFUPM) for funding this work under project number IN151032. They also acknowledge the supported by baseline research fund to S.M.H. by King Abdullah University of Science and Technology.

  作者感谢法赫德国王石油和矿产大学 (KFUPM) 科学研究院长 (DSR) 为在项目编号 IN151032 下资助这项工作提供的支持。他们还感谢阿卜杜拉国王科技大学对 SMH 的基线研究基金的支持。