(S)-1-diphenylphosphino-3-(benzyloxy)propane-2-thiol

• 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: (S)-1-diphenylphosphino-3-(benzyloxy)propane-2-thiol
• 英文别名: (2S)-1-diphenylphosphanyl-3-phenylmethoxypropane-2-thiol
• 化学式: C₂₂H₂₃OPS
• 分子量: 366.464
• InChiKey: XHCJNUXTSPJJLV-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  10.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-苄氧甲基环氧乙烷 在 SC(NH₂)2 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 12.5h， 生成 (S)-1-diphenylphosphino-3-(benzyloxy)propane-2-thiol
  参考文献：
  名称：

  Synthesis and characterization of a new chiral phosphinothiol ligand and its palladium(II) complexes

  摘要：

  The chiral ligand (1-diphenylphosphino-3-benzyloxy)propane-2-thiol 3 has been prepared both in racemic and enantiomerically enriched (92%, e.e.) form. Addition of 2 equiv. of ligand 3 to a solution of [Pd(PPh3)(4)] gave the diastereoisomeric bischelate complexes [Pd(phosphinothiolato)(2)] 4 which exhibit a cis-trans equilibrium in solution. Formation of the diastereoisomeric complexes 4 allows the determination of the enantiomeric purity of ligand 3 by P-31 NMR spectroscopy. Addition of 1 equiv. of ligand 3 to a solution of [PdCl2(PPh3)(2)] gave the enantiomenc complexes [PdCl(phosphinothiolate)(PPh3)] 5, which can be converted to the bischelate complexes 4 by addition of a second equivalent of ligand 3. This process allows the selective preparation of the two diastereoisomeric forms of complex 4. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00143-x

文献信息

• Synthesis and characterization of a new chiral phosphinothiol ligand and its palladium(II) complexes
  作者：Nuria Brugat、Josep Duran、Alfonso Polo、Julio Real、Ángel Álvarez-Larena、J.Francesc Piniella

  DOI：10.1016/s0957-4166(02)00143-x

  日期：2002.4

  The chiral ligand (1-diphenylphosphino-3-benzyloxy)propane-2-thiol 3 has been prepared both in racemic and enantiomerically enriched (92%, e.e.) form. Addition of 2 equiv. of ligand 3 to a solution of [Pd(PPh3)(4)] gave the diastereoisomeric bischelate complexes [Pd(phosphinothiolato)(2)] 4 which exhibit a cis-trans equilibrium in solution. Formation of the diastereoisomeric complexes 4 allows the determination of the enantiomeric purity of ligand 3 by P-31 NMR spectroscopy. Addition of 1 equiv. of ligand 3 to a solution of [PdCl2(PPh3)(2)] gave the enantiomenc complexes [PdCl(phosphinothiolate)(PPh3)] 5, which can be converted to the bischelate complexes 4 by addition of a second equivalent of ligand 3. This process allows the selective preparation of the two diastereoisomeric forms of complex 4. (C) 2002 Elsevier Science Ltd. All rights reserved.