N-n-butyl-Z-3-chloro-2-(methylsulfinyl)propenamide | 1043925-72-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: N-n-butyl-Z-3-chloro-2-(methylsulfinyl)propenamide
• 英文别名: (Z)-N-butyl-3-chloro-2-methylsulfinylprop-2-enamide
• CAS: 1043925-72-9
• 化学式: C₈H₁₄ClNO₂S
• 分子量: 223.724
• InChiKey: AYIHOYDAHLOTBH-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  65.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-n-butyl-Z-3-chloro-2-(methylthio)propenamide 在 Oxone 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 以85%的产率得到N-n-butyl-Z-3-chloro-2-(methylsulfinyl)propenamide
  参考文献：
  名称：

  Investigation of the chemoselective and enantioselective oxidation of α-thio-β-chloroacrylamides

  摘要：

  An investigation of the chemoselective and enantioselective oxidation of alpha-thio-beta-chloroacrylamides is described. The alpha-thio-beta-chloroacrylamides can be selectively oxidised to either the racemic sulfoxide or the sulfone very efficiently. The asymmetric sulfur oxidation of alpha-thio-beta-chloroacrylamides is also discussed, with sulfoxide enantioselectivities of up to 52% ee achieved using the Kagan oxidation, and up to 71% ee when the Bolm oxidation is employed. While the enantioselectivities achieved are modest, these are among the most highly functionalised sulfides investigated in catalytic asymmetric oxidation, and the resulting enantioenriched sulfoxides have significant synthetic potential. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.033

文献信息

• Investigation of the chemoselective and enantioselective oxidation of α-thio-β-chloroacrylamides
  作者：Marie Kissane、Denis Lynch、Jay Chopra、Simon E. Lawrence、Anita R. Maguire

  DOI：10.1016/j.tetasy.2008.04.033

  日期：2008.5

  An investigation of the chemoselective and enantioselective oxidation of alpha-thio-beta-chloroacrylamides is described. The alpha-thio-beta-chloroacrylamides can be selectively oxidised to either the racemic sulfoxide or the sulfone very efficiently. The asymmetric sulfur oxidation of alpha-thio-beta-chloroacrylamides is also discussed, with sulfoxide enantioselectivities of up to 52% ee achieved using the Kagan oxidation, and up to 71% ee when the Bolm oxidation is employed. While the enantioselectivities achieved are modest, these are among the most highly functionalised sulfides investigated in catalytic asymmetric oxidation, and the resulting enantioenriched sulfoxides have significant synthetic potential. (C) 2008 Elsevier Ltd. All rights reserved.