[2S,3R,(S)S]-3-[2-(p-tolylsulfinyl)phenyl]butan-2-ol | 848945-98-2

• 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: [2S,3R,(S)S]-3-[2-(p-tolylsulfinyl)phenyl]butan-2-ol
• 英文别名: (2S,3R)-3-[2-[(S)-(4-methylphenyl)sulfinyl]phenyl]butan-2-ol
• CAS: 848945-98-2
• 化学式: C₁₇H₂₀O₂S
• 分子量: 288.411
• InChiKey: JLZHTKJDEJDZLF-YRVVQQKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [2S,3R,(S)S]-3-[2-(p-tolylsulfinyl)phenyl]butan-2-ol 在 间氯过氧苯甲酸 作用下， 以 氘代氯仿 为溶剂， 生成 [2R,3S]-2-[2-(p-tolylsulfinyl)phenyl]-3-butanol
  参考文献：
  名称：

  Remote Stereocontrol by Sulfinyl Groups:  Reduction of δ-Ketosulfoxides

  摘要：

  [GRAPHICS]The reduction of delta-ketosulfoxides constitutes the first evidence of the efficiency of the sulfinyl group to control the stereoselectivity of 1,5-asymmetric induction processes. The use of DIBAL/Yb(OTf)(3) or L-Selectride as the reducing agents provides delta-hydroxysulfoxides with the opposite configuration at the hydroxylic carbon in a highly stereoselective way.

  DOI：

  10.1021/jo047999j
• 作为产物：
  描述：

  [3R,(S)S]-3-[2-(p-tolylsulfinyl)phenyl]butan-2-one 在 二异丁基氢化铝 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 正庚烷 为溶剂， 反应 1.0h， 以70%的产率得到[2S,3R,(S)S]-3-[2-(p-tolylsulfinyl)phenyl]butan-2-ol
  参考文献：
  名称：

  Remote Stereocontrol by Sulfinyl Groups:  Reduction of δ-Ketosulfoxides

  摘要：

  [GRAPHICS]The reduction of delta-ketosulfoxides constitutes the first evidence of the efficiency of the sulfinyl group to control the stereoselectivity of 1,5-asymmetric induction processes. The use of DIBAL/Yb(OTf)(3) or L-Selectride as the reducing agents provides delta-hydroxysulfoxides with the opposite configuration at the hydroxylic carbon in a highly stereoselective way.

  DOI：

  10.1021/jo047999j

文献信息

• Remote Stereocontrol by Sulfinyl Groups:  Reduction of δ-Ketosulfoxides
  作者：José L. García Ruano、M. Ángeles Fernández-Ibáñez、M. Carmen Maestro、M. Mercedes Rodríguez-Fernández

  DOI：10.1021/jo047999j

  日期：2005.3.1

  [GRAPHICS]The reduction of delta-ketosulfoxides constitutes the first evidence of the efficiency of the sulfinyl group to control the stereoselectivity of 1,5-asymmetric induction processes. The use of DIBAL/Yb(OTf)(3) or L-Selectride as the reducing agents provides delta-hydroxysulfoxides with the opposite configuration at the hydroxylic carbon in a highly stereoselective way.