(R)-2-naphthyl phenacyl sulfoxide | 882430-07-1

• 英文名称: (R)-2-naphthyl phenacyl sulfoxide
• 英文别名: 2-[(R)-naphthalen-2-ylsulfinyl]-1-phenylethanone
• CAS: 882430-07-1
• 化学式: C₁₈H₁₄O₂S
• 分子量: 294.374
• InChiKey: UXCNNNODSYHRIB-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-naphthyl phenacyl sulfoxide 在 二异丁基氢化铝 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (R,R_S)-1-phenyl-2-(2-naphthylsulfinyl)-ethanol 、 (S,R_S)-1-phenyl-2-(2-naphthylsulfinyl)-ethanol
  参考文献：
  名称：

  The synthesis of chiral β-ketosulfoxides by enantioselective oxidation and their stereocontrolled reduction to β-hydroxysulfoxides

  摘要：

  Various chiral non-racemic beta-ketosulfoxides, a class of compounds frequently used in asymmetric synthesis, were prepared in good yields by tert-butyl hydroperoxide oxidation of the corresponding sulfides in the presence of a complex between titanium and (S,S)-hydrobenzoin. The ee values of almost all of the purified products were > 98%. As ascertained by X-ray analysis and/or by NMR spectroscopy, the use of the (S,S)-form of the ligand led to aryl beta-ketosulfoxides with (R-S)-configuration and to methyl phenacyl sulfoxide with the (S-S)-configuration. Some of the aryl ketosulfoxides were subjected to reduction with DIBAL-H/ZnCl2 and the corresponding beta-sulfinylalcohols with an (R,R-S)-configuration produced. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.004
• 作为产物：
  描述：

  2-[(naphthalen-2-yl)sulfanyl]-1-phenylethanone 在 titanium(IV) isopropylate 、 (S,S)-(-)-氢化苯偶姻 、 二叔丁基过氧化物 、 水 作用下， 以 四氯化碳 、 四氢呋喃 为溶剂， 反应 48.5h， 以90%的产率得到(R)-2-naphthyl phenacyl sulfoxide
  参考文献：
  名称：

  The synthesis of chiral β-ketosulfoxides by enantioselective oxidation and their stereocontrolled reduction to β-hydroxysulfoxides

  摘要：

  Various chiral non-racemic beta-ketosulfoxides, a class of compounds frequently used in asymmetric synthesis, were prepared in good yields by tert-butyl hydroperoxide oxidation of the corresponding sulfides in the presence of a complex between titanium and (S,S)-hydrobenzoin. The ee values of almost all of the purified products were > 98%. As ascertained by X-ray analysis and/or by NMR spectroscopy, the use of the (S,S)-form of the ligand led to aryl beta-ketosulfoxides with (R-S)-configuration and to methyl phenacyl sulfoxide with the (S-S)-configuration. Some of the aryl ketosulfoxides were subjected to reduction with DIBAL-H/ZnCl2 and the corresponding beta-sulfinylalcohols with an (R,R-S)-configuration produced. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.004