(1R)1-[3-(hydroxymethyl)phenyl]ethanol | 1253105-74-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R)1-[3-(hydroxymethyl)phenyl]ethanol
• 英文别名: (1R)-1-[3-(hydroxymethyl)phenyl]ethanol
• CAS: 1253105-74-6
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: DSSWHCHVXBFCOZ-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R)1-[3-(hydroxymethyl)phenyl]ethanol 在 M₉ medium 、 Escherichia coli JM₁₀₉ (pVL₂₀₂₈) 作用下， 反应 20.0h， 生成 3-[(1R)-1-hydroxyethyl]benzoic acid
  参考文献：
  名称：

  Multienzymatic preparation of 3-[(1R)-1-hydroxyethyl]benzoic acid and (2S)-hydroxy(phenyl)ethanoic acid

  摘要：

  The use of two oxidoreductases (an aldoketo reductase from Escherichia coli JM109 and an alcohol dehydrogenase from Lactobacillus brevis) has demonstrated that it is possible to prepare enatiomerically pure diols in a one-pot operation. The reactions were applied to the synthesis of (1R)-1-[3-(hydroxymethyl)phenyl]ethanol and (15)-1-phenylethane-1,2-diol, using a two-step procedure. The yield is nearly quantitative and the enantiomeric purity is greater than 95%. A third step has been introduced by adding a cell biocatalyst showing dihydrodiol dehydrogenase activity from Pseudomonas fluorescens N3. This allows for the preparation of 3-[(1R)-1-hydroxyethyl]benzoic acid and (2S)-hydroxy(phenyl)ethanoic acid. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.007
• 作为产物：
  描述：

  3-(1-hydroxyethyl)benzaldehyde 在 Escherichia coli JM₁₀₉ 、 M₉ medium 作用下， 反应 5.0h， 生成 (1R)1-[3-(hydroxymethyl)phenyl]ethanol
  参考文献：
  名称：

  Multienzymatic preparation of 3-[(1R)-1-hydroxyethyl]benzoic acid and (2S)-hydroxy(phenyl)ethanoic acid

  摘要：

  The use of two oxidoreductases (an aldoketo reductase from Escherichia coli JM109 and an alcohol dehydrogenase from Lactobacillus brevis) has demonstrated that it is possible to prepare enatiomerically pure diols in a one-pot operation. The reactions were applied to the synthesis of (1R)-1-[3-(hydroxymethyl)phenyl]ethanol and (15)-1-phenylethane-1,2-diol, using a two-step procedure. The yield is nearly quantitative and the enantiomeric purity is greater than 95%. A third step has been introduced by adding a cell biocatalyst showing dihydrodiol dehydrogenase activity from Pseudomonas fluorescens N3. This allows for the preparation of 3-[(1R)-1-hydroxyethyl]benzoic acid and (2S)-hydroxy(phenyl)ethanoic acid. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.007

文献信息

• Mechanochemical, Water‐Assisted Asymmetric Transfer Hydrogenation of Ketones Using Ruthenium Catalyst
  作者：Vanessza Judit Kolcsár、György Szőllősi

  DOI：10.1002/cctc.202101501

  日期：2022.2.8

  The first highly efficient, aqueous phase mechanochemical asymmetric transfer hydrogenation of prochiral ketones is reported using in situ formed Noyori-Ikariya Ru-complex and sodium formate as hydrogen donor in ball mill.

  使用原位形成的 Noyori-  Ikariya Ru-配合物和甲酸钠作为球磨机中的氢供体，首次报道了前手性酮的高效水相机械化学不对称转移氢化。