6-chloro-2-trimethylsilyl-benzanilide | 146516-68-9

• 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: 6-chloro-2-trimethylsilyl-benzanilide
• 英文别名: 2-chloro-N-phenyl-6-trimethylsilylbenzamide
• CAS: 146516-68-9
• 化学式: C₁₆H₁₈ClNOSi
• 分子量: 303.864
• InChiKey: KIVRITYAXWFMTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  三甲基氯硅烷 、 2-氯-N-苯基苯甲酰胺 在 正丁基锂 作用下， 生成 6-chloro-2-trimethylsilyl-benzanilide
  参考文献：
  名称：

  Application of organolithium and related reagents in synthesis, Part X. Metallation-electrophilic substitution sequence of secondary chlorobenzamides

  摘要：

  The lithiation (Bu(n)Li/THF) of 2-chloro- (1), 3-chloro- (2) and 4-chlorobenzanilides (3) and the subsequent reactions of the corresponding bis-lithiated anilides 4 - 6 with electrophiles (MeI, CH2 = CH - CH2Br, Me3SiCl, MeCHO, o-MeOC6H4CHO, p-MeOC6H4CHO, Me2NCHO and p-MeOC6H4CONMe2) towards the synthesis of the ortho substituted chlorobenzoesic acids derivatives 12 - 14 have been described. The effect of the chlorine substituent upon the generation and stability of the bis-lithiated chloro-anilides 4 - 6 has been studied. It has been found that the bis-lithiated chloro-anilide 5 derived from m-chloro-benzanilide (2) at a temperature above - 30-degrees-C converts into the corresponding benzyne 9. The anilide moiety (masking group) of the formed ortho-substituted chlorobenzanilides appeared to be effectively removable on acid-driven hydrolysis.

  DOI：

  10.1007/bf00808275

文献信息

• Application of organolithium and related reagents in synthesis, Part X. Metallation-electrophilic substitution sequence of secondary chlorobenzamides
  作者：Jan Epsztajn、Adam Bieniek、Justyna A. Kowalska、Jacek Ścianowski

  DOI：10.1007/bf00808275

  日期：1992.12

  The lithiation (Bu(n)Li/THF) of 2-chloro- (1), 3-chloro- (2) and 4-chlorobenzanilides (3) and the subsequent reactions of the corresponding bis-lithiated anilides 4 - 6 with electrophiles (MeI, CH2 = CH - CH2Br, Me3SiCl, MeCHO, o-MeOC6H4CHO, p-MeOC6H4CHO, Me2NCHO and p-MeOC6H4CONMe2) towards the synthesis of the ortho substituted chlorobenzoesic acids derivatives 12 - 14 have been described. The effect of the chlorine substituent upon the generation and stability of the bis-lithiated chloro-anilides 4 - 6 has been studied. It has been found that the bis-lithiated chloro-anilide 5 derived from m-chloro-benzanilide (2) at a temperature above - 30-degrees-C converts into the corresponding benzyne 9. The anilide moiety (masking group) of the formed ortho-substituted chlorobenzanilides appeared to be effectively removable on acid-driven hydrolysis.