(1R,2R)-1-(4'-chlorophenyl)-2-phenylethane-1,2-diol | 62086-76-4

• 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: (1R,2R)-1-(4'-chlorophenyl)-2-phenylethane-1,2-diol
• 英文别名: threo-1-(4'-Chlorphenyl)-2-phenylethandiol；threo-p-Chlordiphenylethandiol；(1R,2R)-1-(4-Chlorophenyl)-2-phenylethane-1,2-diol
• CAS: 62086-76-4
• 化学式: C₁₄H₁₃ClO₂
• 分子量: 248.709
• InChiKey: JKHLGCIYBRKEGD-ZIAGYGMSSA-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：

  (R)-(+)-苯乙醇腈 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 (1R,2R)-1-(4'-chlorophenyl)-2-phenylethane-1,2-diol
  参考文献：
  名称：

  光学活性的4-取代的顺式-1,2-二苯基环氧乙烷及相关的1,2-二苯基乙烷二醇

  摘要：

  合成具有[1 S：2 R ]和[1 R：2 S ]绝对立体化学的赤型1-（4'-氯苯基）-和1-（4'-甲基苯基）-2-苯基乙烷二醇，并将其转化为相应的4通过以下顺序以'-取代的[1 S：2 R ]和[1 R：2 S ]顺式-二苯乙烯氧化物：形成2-甲氧基二恶烷，转化为卤代醇和环化为顺式环氧化物。还产生了大量的光学活性的4'-取代的反式-二苯乙烯氧化物。环氧酶水合酶的立体选择性在[ S顺式-二苯乙烯氧化物的碳原子以构型反转产生[ R：R ]二醇。实现了顺式-1-（4'-硝基苯基）-2-苯基环氧乙烷的简便酶解。描述了包括上述化合物的CD光谱在内的光学性质。

  DOI：

  10.1016/0040-4020(76)85110-1

文献信息

• Choudary, Boyapati M.; Chowdari, Naidu S.; Madhi, Sateesh, Angewandte Chemie - International Edition, 2001, vol. 40, # 24, p. 4620 - 4623
  作者：Choudary, Boyapati M.、Chowdari, Naidu S.、Madhi, Sateesh、Kantam, Mannepalli L.

  DOI：——

  日期：——
• Microbial reduction of a series of substituted benzils. Optical properties and nuclear magnetic resonance spectra of products
  作者：Mitsuru Imuta、Herman Ziffer

  DOI：10.1021/jo00411a012

  日期：1978.8
• 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.
• The enhanced asymmetric hydrogenation of unsymmetrical benzils to hydrobenzoin catalyzed by organosoluble zirconium phosphonate-immobilized ruthenium catalyst
  作者：Yu Du、Dandan Feng、Jingwei Wan、Xuebing Ma

  DOI：10.1016/j.apcata.2014.03.039

  日期：2014.6

  In this article, a successful design on translating a heterogeneous catalysis of chiral zirconium phosphonate-supported ruthenium catalyst into a homogeneous system was developed by the covalent attachment of chiral (R,R)-1,2-diphenyl-ethylenediamine [(R,R)-DPEN] into the backbone of zirconium phosphonate with the different arm lengths (n = 2, 4, 6) and immobilization of [RuCl2(p-cymene)](2). Their catalytic performances in the homogeneous asymmetric transfer hydrogenation of unsymmetrical benzils with m- and p-substituents were enhanced, and the excellent activities (>97.1% conv.), diastereomeric and enantiomeric purities (syn/anti = 11.0-29.4, 91.8-99.2%ee syn) were achieved. These homogeneous supported Ru catalysts could be quantitatively and readily recovered by addition of ethyl acetate and centrifugation by solid/liquid separation, and be reused for five times without significant loss of their catalytic performances with 97.0% conv., 95.6% syn and syn/anti = 20.7. (C) 2014 Elsevier B.V. All rights reserved.
• METWALLY, MOHAMMED EL-SAYED;WOLFE, N. LEE, ENVIRON. TOXICOL. AND CHEM., 8,(1989) N, C. 553-562
  作者：METWALLY, MOHAMMED EL-SAYED、WOLFE, N. LEE

  DOI：——

  日期：——