syn-1-(2-bromophenyl)-2-phenylethane-1,2-diol | 1146729-43-2

• 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: syn-1-(2-bromophenyl)-2-phenylethane-1,2-diol
• CAS: 1146729-43-2
• 化学式: C₁₄H₁₃BrO₂
• 分子量: 293.16
• InChiKey: MRTURAQBIQHKEP-ZIAGYGMSSA-N

物化性质

• 沸点：
  425.1±40.0 °C(predicted)
• 密度：
  1.498±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  o-bromo-trans-stilbene oxide 在 Amberlist 15 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 20.0h， 以50%的产率得到
  参考文献：
  名称：

  A mild access to chiral syn 1,2-diaryl glycols by stereoselective ring opening of ortho substituted trans 2,3-diaryl-oxiranes using Amberlyst 15 in H2O/THF system

  摘要：

  Amberlyst 15 was an efficient and green catalyst for the reaction of 2,3-diaryloxiranes with H2O in organic co-solvent to prepare glycols in high yield. Ortho substituted trans 2,3-diaryloxiranes afforded the corresponding syn glycols stereo- and enantiospecifically. Stereoselectivity appeared related to the coordination ability of the substituents, irrespective of their electronic properties. Indeed o-OCH3 and o-OBn substituted syn glycols were obtained in high stereochemical ratios (6/1 and 10/1, respectively), and o-OTIPS and o-NO2 substituted ones were obtained as exclusive products, with the same ee of the parent epoxides. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.039

文献信息

• Bidirectional Metalation of Hydrobenzoin: Direct Access to New Chiral Ligands and Auxiliaries
  作者：Inhee Cho、Labros Meimetis、Robert Britton

  DOI：10.1021/ol900323u

  日期：2009.5.7

  A bidirectional ortho metalation of the readily available chiral diol hydrobenzoin has been developed that provides direct access to new ortho-functionalized hydrobenzoin derivatives. This one-pot procedure should broaden the utility of hydrobenzoin as an auxiliary and ligand in asymmetric synthesis.
• 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.