N-4'-fluorophenyl-Z-3-chloro-2-(n-butylsulfinyl)propenamide | 1043925-60-5

• 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: N-4'-fluorophenyl-Z-3-chloro-2-(n-butylsulfinyl)propenamide
• 英文别名: (Z)-2-butylsulfinyl-3-chloro-N-(4-fluorophenyl)prop-2-enamide
• CAS: 1043925-60-5
• 化学式: C₁₃H₁₅ClFNO₂S
• 分子量: 303.785
• InChiKey: STQQPJJWGNKEQC-XFXZXTDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  65.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-4'-fluorophenyl-Z-3-chloro-2-(n-butylsulfinyl)propenamide 、 环戊二烯 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 2-endo-(n-butylsulfinyl)-3-endo-chlorobicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid 4'-fluorophenylamide 、 2-exo-(n-butylsulfinyl)-3-exo-chlorobicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid 4'-fluorophenylamide
  参考文献：
  名称：

  The influence of reaction conditions on the Diels–Alder cycloadditions of 2-thio-3-chloroacrylamides; investigation of thermal, catalytic and microwave conditions

  摘要：

  介绍了在热、催化和微波条件下，环戊二烯和 2,3-二甲基-1,3-丁二烯与一系列 2-硫代-3-氯丙烯酰胺的 DielsâAlder 环加成反应。讨论了反应条件对环化反应结果的影响，特别是立体选择性和反应效率。虽然环化反应是在硫化物、亚砜和砜的氧化水平上进行的，但使用亚砜衍生物显然有利于立体选择性地构建 DielsâAlder 环加成物。

  DOI：

  10.1039/c0ob00368a
• 作为产物：
  描述：

  N-4'-fluorophenyl-Z-3-chloro-2-(n-butylthio)propenamide 在 Oxone 作用下， 以 水 、 丙酮 为溶剂， 反应 1.5h， 以95%的产率得到N-4'-fluorophenyl-Z-3-chloro-2-(n-butylsulfinyl)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

• The influence of reaction conditions on the Diels–Alder cycloadditions of 2-thio-3-chloroacrylamides; investigation of thermal, catalytic and microwave conditions
  作者：Marie Kissane、Denis Lynch、Jay Chopra、Simon E. Lawrence、Anita R. Maguire

  DOI：10.1039/c0ob00368a

  日期：——

  The Diels–Alder cycloadditions of cyclopentadiene and 2,3-dimethyl-1,3-butadiene to a range of 2-thio-3-chloroacrylamides under thermal, catalytic and microwave conditions is described. The influence of reaction conditions on the outcome of the cycloadditions, in particular the stereoselectivity and reaction efficiency, is discussed. While the cycloadditions have been attempted at the sulfide, sulfoxide and sulfone levels of oxidation, use of the sulfoxide derivatives is clearly beneficial for stereoselective construction of Diels–Alder cycloadducts.

  介绍了在热、催化和微波条件下，环戊二烯和 2,3-二甲基-1,3-丁二烯与一系列 2-硫代-3-氯丙烯酰胺的 DielsâAlder 环加成反应。讨论了反应条件对环化反应结果的影响，特别是立体选择性和反应效率。虽然环化反应是在硫化物、亚砜和砜的氧化水平上进行的，但使用亚砜衍生物显然有利于立体选择性地构建 DielsâAlder 环加成物。
• 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.