N-(2-(S)-benzyloxypropionyl)-2-methylthioaniline | 1215018-80-6

• 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-(2-(S)-benzyloxypropionyl)-2-methylthioaniline
• 英文别名: (2S)-N-(2-methylsulfanylphenyl)-2-phenylmethoxypropanamide
• CAS: 1215018-80-6
• 化学式: C₁₇H₁₉NO₂S
• 分子量: 301.409
• InChiKey: FZDHVNDHKKOZGM-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-叔丁基-3-碘苯 、 N-(2-(S)-benzyloxypropionyl)-2-methylthioaniline 在 palladium diacetate 、 potassium carbonate 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 22.0h， 生成 N-(2-(S)-benzyloxy-3-(4-tert-butylphenyl)-propionyl)-2-methylthioaniline 、 N-(2-(R)-benzyloxy-3-(4-tert-butylphenyl)-propionyl)-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 、 (S)-2-benzyloxypropanoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(2-(S)-benzyloxypropionyl)-2-methylthioaniline 、 N-(2-(R)-benzyloxypropionyl)-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

• 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.