N-(hydrocinnamoyl)-2-methylthioaniline | 708222-26-8

• 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-(hydrocinnamoyl)-2-methylthioaniline
• 英文别名: N-[2-(methylthio)phenyl]-3-phenylpropanamide；N-(2-methylsulfanylphenyl)-3-phenylpropanamide
• CAS: 708222-26-8
• 化学式: C₁₆H₁₇NOS
• 分子量: 271.383
• InChiKey: XSDSDAVSFHFVHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(hydrocinnamoyl)-2-methylthioaniline 、 1,3-二甲基-5-碘苯 在 palladium diacetate 、 potassium carbonate 、 三甲基乙酸 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 39.0h， 以47%的产率得到N-(3-(3,5-dimethylphenyl)-3-phenylpropionyl)-2-methylthioaniline
  参考文献：
  名称：

  Auxiliary-Assisted Palladium-Catalyzed Arylation and Alkylation of sp² and sp³ Carbon−Hydrogen Bonds

  摘要：

  We have developed a method for auxiliary-directed, palladium-catalyzed beta-arylation and alkylation of sp(3) and sp(2) C-H bonds in carboxylic acid derivatives. The method employs a carboxylic acid 2-methylthioaniline- or 8-aminoquinoline amide substrate, aryl or alkyl iodide coupling partner, palladium acetate catalyst, and an inorganic base. By employing 2-methylthioaniline auxiliary, selective monoarylation of primary sp(3) C-H bonds can be achieved. If arylation of secondary sp(3) C-H bonds is desired, 8-aminoquinoline auxiliary may be used. For alkylation of sp(3) and sp(2) C-H bonds, 8-aminoquinoline auxiliary affords the best results. Some functional group tolerance is observed and amino- and hydroxy-acid derivatives can be functionalized. Preliminary mechanistic studies have been performed. A palladacycle intermediate has been isolated, characterized by X-ray crystallography, and its reactions have been studied.

  DOI：

  10.1021/ja910900p
• 作为产物：
  描述：

  2-氨基茴香硫醚 、 3-苯丙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到N-(hydrocinnamoyl)-2-methylthioaniline
  参考文献：
  名称：

  Auxiliary-Assisted Palladium-Catalyzed Arylation and Alkylation of sp² and sp³ Carbon−Hydrogen Bonds

  摘要：

  We have developed a method for auxiliary-directed, palladium-catalyzed beta-arylation and alkylation of sp(3) and sp(2) C-H bonds in carboxylic acid derivatives. The method employs a carboxylic acid 2-methylthioaniline- or 8-aminoquinoline amide substrate, aryl or alkyl iodide coupling partner, palladium acetate catalyst, and an inorganic base. By employing 2-methylthioaniline auxiliary, selective monoarylation of primary sp(3) C-H bonds can be achieved. If arylation of secondary sp(3) C-H bonds is desired, 8-aminoquinoline auxiliary may be used. For alkylation of sp(3) and sp(2) C-H bonds, 8-aminoquinoline auxiliary affords the best results. Some functional group tolerance is observed and amino- and hydroxy-acid derivatives can be functionalized. Preliminary mechanistic studies have been performed. A palladacycle intermediate has been isolated, characterized by X-ray crystallography, and its reactions have been studied.

  DOI：

  10.1021/ja910900p

文献信息

• Mild N-deacylation of secondary amides by alkylation with organocerium reagents
  作者：Ai-E Wang、Zong Chang、Yong-Peng Liu、Pei-Qiang Huang

  DOI：10.1016/j.cclet.2015.05.033

  日期：2015.9

  Secondary amides are a class of highly stable compounds serving as versatile starting materials, intermediates and directing groups (amido groups) in organic synthesis. The direct deacylation of secondary amides to release amines is an important transformation in organic synthesis. Here, we report a protocol for the deacylation of secondary amides and isolation of amines. The method is based on the activation

  摘要仲酰胺是一类高度稳定的化合物，可作为有机合成中的通用原料，中间体和指导基团（酰胺基）。仲酰胺的直接脱酰以释放胺是有机合成中的重要转变。在这里，我们报告了仲酰胺脱酰和胺分离的方案。该方法基于用Tf 2 O活化酰胺，然后添加有机铈试剂，然后进行酸性处理。反应在温和的条件下进行，以高收率得到相应的胺，以其盐酸盐的形式分离出来。与CH活化功能化方法相结合，该方法适用于苯胺的功能化以及羧酸衍生物向功能化酮的转化。
• Auxiliary-Assisted Palladium-Catalyzed Arylation and Alkylation of sp² and sp³ Carbon−Hydrogen Bonds
  作者：Dmitry Shabashov、Olafs Daugulis

  DOI：10.1021/ja910900p

  日期：2010.3.24

  We have developed a method for auxiliary-directed, palladium-catalyzed beta-arylation and alkylation of sp(3) and sp(2) C-H bonds in carboxylic acid derivatives. The method employs a carboxylic acid 2-methylthioaniline- or 8-aminoquinoline amide substrate, aryl or alkyl iodide coupling partner, palladium acetate catalyst, and an inorganic base. By employing 2-methylthioaniline auxiliary, selective monoarylation of primary sp(3) C-H bonds can be achieved. If arylation of secondary sp(3) C-H bonds is desired, 8-aminoquinoline auxiliary may be used. For alkylation of sp(3) and sp(2) C-H bonds, 8-aminoquinoline auxiliary affords the best results. Some functional group tolerance is observed and amino- and hydroxy-acid derivatives can be functionalized. Preliminary mechanistic studies have been performed. A palladacycle intermediate has been isolated, characterized by X-ray crystallography, and its reactions have been studied.