(1S,2S,3R)-1,3-diphenyl-1,2-butanediol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (1S,2S,3R)-1,3-diphenyl-1,2-butanediol
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: YORQCFGOKXHWHO-KCXAZCMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (E)-1,3-diphenyl-1-butene 在 甲基磺酰胺 、 水 作用下， 以 叔丁醇 为溶剂， 反应 24.0h， 生成 (1S,2S,3R)-1,3-diphenyl-1,2-butanediol 、 (1R,2R,3R)-1,3-diphenyl-1,2-butanediol
  参考文献：
  名称：

  Enantioselective Preparation of C2-Symmetrical Ferrocenyl Ligands for Asymmetric Catalysis

  摘要：

  Corey - Bakshi - Shibata (CBS) reduction of the 1,1'-diacylmetallocenes 5 and 7 provides the C-2-symmetrical diols 4 and 10, which proved to be useful starting materials for stereo-controlled ligand synthesis. Diols 4 and 10 can be easily converted to a wide range of diamines, diphosphines, and dithioacetates by nucleophilic substitution of the hydroxyl function with full retention of configuration. Furthermore, the aminophosphines 30 and 31 become easily accessible. Compounds 30 and 31 have been used as ligands in enantioselective cross-coupling of racemic secondary Grignard reagents with vinyl bromides, A selectivity up to 93% ee could be reached for the first time in the preparation of (S)-(E)-1,3-diphenyl-1-butene (34b), which was transformed into the enantiomerically pure chiral building block 37 with a pseudoasymmetric center in a straightforward, three-step synthesis.

  DOI：

  10.1002/(sici)1521-3765(19980515)4:5<950::aid-chem950>3.0.co;2-b

文献信息

• Enantioselective Preparation of C2-Symmetrical Ferrocenyl Ligands for Asymmetric Catalysis
  作者：Lothar Schwink、Paul Knochel

  DOI：10.1002/(sici)1521-3765(19980515)4:5<950::aid-chem950>3.0.co;2-b

  日期：——

  Corey - Bakshi - Shibata (CBS) reduction of the 1,1'-diacylmetallocenes 5 and 7 provides the C-2-symmetrical diols 4 and 10, which proved to be useful starting materials for stereo-controlled ligand synthesis. Diols 4 and 10 can be easily converted to a wide range of diamines, diphosphines, and dithioacetates by nucleophilic substitution of the hydroxyl function with full retention of configuration. Furthermore, the aminophosphines 30 and 31 become easily accessible. Compounds 30 and 31 have been used as ligands in enantioselective cross-coupling of racemic secondary Grignard reagents with vinyl bromides, A selectivity up to 93% ee could be reached for the first time in the preparation of (S)-(E)-1,3-diphenyl-1-butene (34b), which was transformed into the enantiomerically pure chiral building block 37 with a pseudoasymmetric center in a straightforward, three-step synthesis.