(1S,2S)-1-(4'-chlorophenyl)-2-phenylethane-1,2-diol | 650601-06-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1S,2S)-1-(4'-chlorophenyl)-2-phenylethane-1,2-diol
• 英文别名: 1-(4-chloro-phenyl)-2-phenyl-ethane-1,2-diol；(1S,2S)-1-(4-Chlorophenyl)-2-phenylethane-1,2-diol
• CAS: 650601-06-2
• 化学式: C₁₄H₁₃ClO₂
• 分子量: 248.709
• InChiKey: JKHLGCIYBRKEGD-KBPBESRZSA-N

物化性质

• 沸点：
  406.6±40.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(4-chlorophenyl)-2-phenylethanol 在 AD-mix-α 、 甲基磺酰胺 、 硫酸 作用下， 以 1,4-二氧六环 、 水 、 叔丁醇 为溶剂， 反应 50.17h， 生成 (1S,2S)-1-(4'-chlorophenyl)-2-phenylethane-1,2-diol
  参考文献：
  名称：

  Studies on biotransformation of (±)-1-(4′-chlorophenyl)-2-phenylethanol

  摘要：

  The metabolism of (+/-)-1-4'-chlorophenyl)-2-phenylethanol 1 by the phytopathogenic fungi Colletotrichum gloeosporioides and Botrytis cinerea has been studied. Regioselective monooxygenase-catalyzed hydroxylation of C-H bonds yielded the corresponding diols, the ratios of which showed a clear preference for the C-H benzylic bond. in-Hydroxylation in the substituted aromatic ring, a rarely described phenomenon, has been observed and with good enantioselectivity. The chemistry involved ill determining the configuration of the biotransformation products is also described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.026

文献信息

• Asymmetric transfer hydrogenation of unsymmetrical benzils
  作者：Hao Zhang、Dandan Feng、Haibo Sheng、Xuebing Ma、Jinwei Wan、Qian Tang

  DOI：10.1039/c3ra47129b

  日期：——

  asymmetric transfer hydrogenation of unsymmetrical benzils with m, p-substituents was conducted with a substrate/catalyst molar ratio of 100 at 40 °C for 24 h to produce (S,S)-hydrobenzoins in good yields (76.2% to 97.1%) with high diastereomeric (syn/anti = 10.8 to 29.7/1) and enantiomeric purities (86.1%ee syn to 98.9%ee syn). Unfortunately, the unsymmetrical benzils with the o-substituents such as electron-donating

  本文以40℃为底物/催化剂摩尔比为100的m / p取代基对不对称苯进行不对称转移氢化反应24小时，从而以良好的收率生产了（S，S）-氢安息香素（76.2％高非对映异构体（syn / anti = 10.8至29.7 / 1）和对映体纯度（86.1％ee syn至98.9％ee syn）达到97.1％）。不幸的是，具有o取代基（例如给电子（R = CH 3，OCH 3）和吸电子基团（R = F，Cl，CF 3）的非对称苯））即使在40°C下持续72 h也导致收率低（0％至31.2％）。这些产物由于空间效应而导致无效的非对映选择性（syn / anti = 1.5至5.0 / 1）。此外，以动态动力学研究的结果为例，以3-甲氧基-1，2-二苯基乙二酮为例，提出了不对称苯的合理反应途径。
• Stereoselective Synthesis of Optically Active Hydrobenzoins via Asymmetric Hydrogenation of Benzils with Ru(OTf)(TsDPEN)(η6-cymene) as the Pre-catalyst
  作者：Xiaofei Huang、Naikai Li、Zhicong Geng、Fengfeng Pan、Xingwang Wang

  DOI：10.1002/cjoc.201200393

  日期：2012.8.14

  Optically active hydrobenzoins are very important building blocks for further derivation of biologically active complexes, natural products, and pharmaceutical compounds. In this paper, A practical approach has been developed for asymmetric hydrogenation of benzils with Ru(OTf)(TsDPEN)(η6‐cymene) as a pre‐catalyst in methanol. Therefore, a series of chiral hydrobenzoins was synthesized in good yields

  光学活性氢安息香素是进一步衍生生物活性复合物，天然产物和药物化合物的重要组成部分。在本文中，一个实用的方法已被用于与钌苯偶酰的不对称氢化显影（OTF）（TsDPEN）（η 6 -cymene）作为在甲醇中的预催化剂。因此，以良好的产率合成了一系列手性的氢安息香素，具有良好至中等的非对映选择性和良好至优异的对映选择性。
• Studies on biotransformation of (±)-1-(4′-chlorophenyl)-2-phenylethanol
  作者：Antonio J. Bustillo、Carlos M. Garcı́a-Pajón、Josefina Aleu、Rosario Hernández-Galán、Isidro G. Collado

  DOI：10.1016/j.tetasy.2003.08.026

  日期：2003.11

  The metabolism of (+/-)-1-4'-chlorophenyl)-2-phenylethanol 1 by the phytopathogenic fungi Colletotrichum gloeosporioides and Botrytis cinerea has been studied. Regioselective monooxygenase-catalyzed hydroxylation of C-H bonds yielded the corresponding diols, the ratios of which showed a clear preference for the C-H benzylic bond. in-Hydroxylation in the substituted aromatic ring, a rarely described phenomenon, has been observed and with good enantioselectivity. The chemistry involved ill determining the configuration of the biotransformation products is also described. (C) 2003 Elsevier Ltd. All rights reserved.