(3R)-1,3-diphenyl-3-phenylsulfanylpropan-1-ol | 500296-11-7

• 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: (3R)-1,3-diphenyl-3-phenylsulfanylpropan-1-ol
• CAS: 500296-11-7
• 化学式: C₂₁H₂₀OS
• 分子量: 320.455
• InChiKey: HYKWPMRRDSXSMG-BPGUCPLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 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：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R)-1,3-diphenyl-3-phenylsulfanylpropan-1-ol 在 potassium bromide 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 碳酸氢钠 、 sodium carbonate 作用下， 以 二氯甲烷 、 水 、 xylene 为溶剂， 反应 3.0h， 生成 (R)-(E)-1,3-diphenyl-prop-2-en-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
• 作为产物：
  描述：

  (3R)-(+)-1,3-diphenyl-3-phenylsulfanylpropan-1-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以98%的产率得到(3R)-1,3-diphenyl-3-phenylsulfanylpropan-1-ol
  参考文献：
  名称：

  1,3-二芳基-3-苯基硫烷基-1-丙醇在[1,3] -PhS移位的参与下环化为硫代苯并二氢吡喃

  摘要：

  光学活性的（3 - [R，1个RS）-3-芳基-1-苯基-3-苯硫基-1-丙醇是容易脱水形成主要外消旋-顺式-2-芳基-4- phenylthiochroman，和外消旋-顺式-4 -芳基-2-苯基硫代苯并二氢吡喃和相应的反式异构体。所观察到的反应的结果（重排和外消旋化）从S显然导致Ë涉及异常1,3-苯硫基组迁移的Ar反应。假定中间体的理论研究（DFT）结果支持了这种解释。

  DOI：

  10.1016/s0040-4020(03)00519-2

文献信息

• Cyclization of 1,3-diaryl-3-phenylsulfanyl-1-propanols to thiochromans with the participation of [1,3]-PhS shift
  作者：Jacek Skarżewski、Mariola Zielińska-Błajet、Szczepan Roszak、Ilona Turowska-Tyrk

  DOI：10.1016/s0040-4020(03)00519-2

  日期：2003.5

  Optically active (3R,1RS)-3-aryl-1-phenyl-3-phenylsulfanyl-1-propanols were easily dehydrated forming mainly rac-cis-2-aryl-4-phenylthiochroman, and rac-cis-4-aryl-2-phenylthiochroman along with the corresponding trans-isomers. The observed reaction outcome (rearrangement and racemisation) apparently results from the SEAr reaction involving the unusual 1,3-phenylsulfanyl group migration. This interpretation

  光学活性的（3 - [R，1个RS）-3-芳基-1-苯基-3-苯硫基-1-丙醇是容易脱水形成主要外消旋-顺式-2-芳基-4- phenylthiochroman，和外消旋-顺式-4 -芳基-2-苯基硫代苯并二氢吡喃和相应的反式异构体。所观察到的反应的结果（重排和外消旋化）从S显然导致Ë涉及异常1,3-苯硫基组迁移的Ar反应。假定中间体的理论研究（DFT）结果支持了这种解释。
• 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.