(R)-4-(1-hydroxyethyl)phenylboronic acid | 1351956-01-8

• 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: (R)-4-(1-hydroxyethyl)phenylboronic acid
• 英文别名: [4-[(1R)-1-hydroxyethyl]phenyl]boronic acid
• CAS: 1351956-01-8
• 化学式: C₈H₁₁BO₃
• 分子量: 165.985
• InChiKey: QORATNLZEOZUPG-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.58
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-乙酰基苯硼酸 在 异丙醇 、 还原型辅酶II(NADPH)四钠盐 作用下， 反应 24.0h， 生成 (R)-4-(1-hydroxyethyl)phenylboronic acid
  参考文献：
  名称：

  Stereocomplementary asymmetric bioreduction of boron-containing ketones mediated by alcohol dehydrogenases

  摘要：

  Optically active boron-containing alcohols were prepared via the stereoselective reduction of the corresponding carbonyl compounds by alcohol dehydrogenases. Depending on the substrate, both (R)-alcohols and (S)-alcohols were obtained with excellent enantioselectivity (up to >99% ee) employing either ADH-A or LB-ADH. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.10.012

文献信息

• Lipase-Catalyzed Highly Enantioselective Kinetic Resolution of Boron-Containing Chiral Alcohols
  作者：Leandro H. Andrade、Thiago Barcellos

  DOI：10.1021/ol901091f

  日期：2009.7.16

  to obtain optically pure boron compounds is described. The kinetic resolution of boron-containing chiral alcohols via enantioselective transesterification catalyzed by lipases was studied. Aromatic, allylic, and aliphatic secondary alcohols containing a boronate ester or boronic acid group were resolved by lipase from Candida antartica (CALB), and excellent E values (E > 200) and high enantiomeric excesses

  描述了酶作为催化剂首次获得光学纯硼化合物的应用。研究了含硼手性醇通过脂肪酶催化的对映选择性酯交换反应的动力学拆分。含有硼酸酯或硼酸基团的芳族，烯丙基和脂族仲醇可通过南极假丝酵母（CALB）的脂肪酶分解，并具有出色的E值（E > 200）和高对映体过量（最高> 99％）获得底物和乙酰化产物。
• Stereocomplementary asymmetric bioreduction of boron-containing ketones mediated by alcohol dehydrogenases
  作者：Thiago Barcellos、Katharina Tauber、Wolfgang Kroutil、Leandro H. Andrade

  DOI：10.1016/j.tetasy.2011.10.012

  日期：2011.10

  Optically active boron-containing alcohols were prepared via the stereoselective reduction of the corresponding carbonyl compounds by alcohol dehydrogenases. Depending on the substrate, both (R)-alcohols and (S)-alcohols were obtained with excellent enantioselectivity (up to >99% ee) employing either ADH-A or LB-ADH. (C) 2011 Elsevier Ltd. All rights reserved.