(1S,3R)-1,3-diphenyl-3-phenylsulfonylpropan-1-ol | 500296-12-8

• 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,3R)-1,3-diphenyl-3-phenylsulfonylpropan-1-ol
• 英文别名: (1S,3R)-3-(benzenesulfonyl)-1,3-diphenylpropan-1-ol
• CAS: 500296-12-8
• 化学式: C₂₁H₂₀O₃S
• 分子量: 352.454
• InChiKey: JTRGNSXBXPJMKV-LEWJYISDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,3R)-1,3-diphenyl-3-phenylsulfonylpropan-1-ol 在 18-冠醚-6 、 potassium tert-butylate 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 (-)-(1R,2R)-1,2-diphenyl-1-phenylsulfonylcyclopropane
  参考文献：
  名称：

  A new and efficient route to homochiral γ-hydroxysulfoxides and γ-hydroxysulfones

  摘要：

  Readily available (+)- (R)-1,3-diphenyl-3-phenylsulfanyl-propan-1-one 1 was oxidized to the corresponding sulfone and its reduction gave separable (1R,3R)- and (1S,3R)-1,3-diphenyl-3-phenylsulfonylpropan-1-ols. When I was reduced to the mixture of epimeric alcohols, subsequent reaction with three different sulfoxidation agents allowed the separation of all four diastereomeric, 1,3-diphenyl-3-phenylsulfinylpropan-1-ols in diastereomerically pure form. The absolute configuration at the newly created stereogenic carbon was proved by chemical correlation, while the configuration of the sulfur centre of the phenylsulfinyl group was established by CD spectroscopy. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00581-5
• 作为产物：
  描述：

  (3R)-(+)-1,3-diphenyl-3-phenylsulfanylpropan-1-one 在 lithium aluminium tetrahydride 、 Oxone 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 5.0h， 生成 (1S,3R)-1,3-diphenyl-3-phenylsulfonylpropan-1-ol
  参考文献：
  名称：

  A new and efficient route to homochiral γ-hydroxysulfoxides and γ-hydroxysulfones

  摘要：

  Readily available (+)- (R)-1,3-diphenyl-3-phenylsulfanyl-propan-1-one 1 was oxidized to the corresponding sulfone and its reduction gave separable (1R,3R)- and (1S,3R)-1,3-diphenyl-3-phenylsulfonylpropan-1-ols. When I was reduced to the mixture of epimeric alcohols, subsequent reaction with three different sulfoxidation agents allowed the separation of all four diastereomeric, 1,3-diphenyl-3-phenylsulfinylpropan-1-ols in diastereomerically pure form. The absolute configuration at the newly created stereogenic carbon was proved by chemical correlation, while the configuration of the sulfur centre of the phenylsulfinyl group was established by CD spectroscopy. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00581-5

文献信息

• A new and efficient route to homochiral γ-hydroxysulfoxides and γ-hydroxysulfones
  作者：Jacek Skarżewski、Renata Siedlecka、Elżbieta Wojaczyńska、Mariola Zielińska-Błajet

  DOI：10.1016/s0957-4166(02)00581-5

  日期：2002.10

  Readily available (+)- (R)-1,3-diphenyl-3-phenylsulfanyl-propan-1-one 1 was oxidized to the corresponding sulfone and its reduction gave separable (1R,3R)- and (1S,3R)-1,3-diphenyl-3-phenylsulfonylpropan-1-ols. When I was reduced to the mixture of epimeric alcohols, subsequent reaction with three different sulfoxidation agents allowed the separation of all four diastereomeric, 1,3-diphenyl-3-phenylsulfinylpropan-1-ols in diastereomerically pure form. The absolute configuration at the newly created stereogenic carbon was proved by chemical correlation, while the configuration of the sulfur centre of the phenylsulfinyl group was established by CD spectroscopy. (C) 2002 Elsevier Science Ltd. All rights reserved.