((1R,2S)-1-(4-bromophenylthio)-3-methoxy-1-phenylpropan-2-yloxy)diphenylphosphine | 1221576-61-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ((1R,2S)-1-(4-bromophenylthio)-3-methoxy-1-phenylpropan-2-yloxy)diphenylphosphine
• 英文别名: [(1R,2S)-1-(4-bromophenyl)sulfanyl-3-methoxy-1-phenylpropan-2-yl]oxy-diphenylphosphane
• CAS: 1221576-61-9
• 化学式: C₂₈H₂₆BrO₂PS
• 分子量: 537.457
• InChiKey: HNGZTTWBDIGBCW-WUFINQPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-溴苯硫酚 、 (2S,3S)-2-(甲氧基甲基)-3-苯基环氧乙烷 在 4-二甲氨基吡啶 、 三乙胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 甲苯 为溶剂， 反应 0.33h， 生成 ((1R,2S)-1-(4-bromophenylthio)-3-methoxy-1-phenylpropan-2-yloxy)diphenylphosphine
  参考文献：
  名称：

  Modular optimization of enantiopure epoxide-derived P,S-ligands for rhodium-catalyzed hydrogenation of dehydroamino acids

  摘要：

  The optimization of P,S-ligands derived from enantiopure (2S,3S)-phenylglycidol for asymmetric rhodium-catalyzed hydrogenation of dehydroamino esters is described. The exceptionally high modular character of the (25,3S)-phenylglycidol platform is demonstrated by systematic modification of the ether and thioether moieties, the skeletal aryl substituent and the stereo and regiochemistry of the ligands. An experimentally useful method for the monitoring of hydrogenation reactions is also described and used for obtaining relevant data of the catalytic systems studied. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.050

文献信息

• Phosphinite Thioethers Derived from Chiral Epoxides. Modular <i>P</i>,<i>S</i>-Ligands for Pd-Catalyzed Asymmetric Allylic Substitutions
  作者：Xisco Caldentey、Miquel A. Pericàs

  DOI：10.1021/jo100223w

  日期：2010.4.16

  prepared from enantiopure arylglycidols. These ligands have been iteratively optimized with respect to four different structural parameters for use in Pd-catalyzed allylic substitutions. As a final output, highly active and enantioselective ligands for these synthetically important transformations have been developed, and the factors controlling their catalytic behavior have been rationalized. From a methodological

  从对映体纯的芳基糖醇制备了新的模块化P，S-配体家族。这些配体已经针对用于Pd催化的烯丙基取代的四个不同的结构参数进行了迭代优化。作为最终产物，已经开发了用于这些合成上重要的转化的高活性和对映选择性配体，并且已经合理地控制了它们的催化行为的因素。从方法学的观点出发，已经开发了一种方便的方法，用于用大体积的硫醇对顺式-缩水甘油酯进行区域选择性开环，以产生相应的β-烷硫基-α-羟基羧酸。
• Modular optimization of enantiopure epoxide-derived P,S-ligands for rhodium-catalyzed hydrogenation of dehydroamino acids
  作者：Xisco Caldentey、Xacobe C. Cambeiro、Miquel A. Pericàs

  DOI：10.1016/j.tet.2011.04.050

  日期：2011.6

  The optimization of P,S-ligands derived from enantiopure (2S,3S)-phenylglycidol for asymmetric rhodium-catalyzed hydrogenation of dehydroamino esters is described. The exceptionally high modular character of the (25,3S)-phenylglycidol platform is demonstrated by systematic modification of the ether and thioether moieties, the skeletal aryl substituent and the stereo and regiochemistry of the ligands. An experimentally useful method for the monitoring of hydrogenation reactions is also described and used for obtaining relevant data of the catalytic systems studied. (C) 2011 Elsevier Ltd. All rights reserved.