3-chloro-N-allyl-N-methyl-benzamide

• 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: 3-chloro-N-allyl-N-methyl-benzamide
• 英文别名: 3-chloro-N-methyl-N-prop-2-enylbenzamide
• 化学式: C₁₁H₁₂ClNO
• 分子量: 209.675
• InChiKey: LJRLRGNNUBLPMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  丙醇 、 3-chloro-N-allyl-N-methyl-benzamide 在 rhodium(III) chloride 作用下， 反应 4.0h， 以92%的产率得到3-氯-N-甲基苯甲酰胺
  参考文献：
  名称：

  One-Step RhCl₃-Catalyzed Deprotection of Acyclic N-Allyl Amides

  摘要：

  [GRAPHICS]A convenient one-step RhCl3-catalyzed deprotection of acyclic N-allyl amides is described. Preliminary mechanistic studies reveal that the key to the success of the one-step deprotection process is the dual function of RhCl3 in alcohol solvents. Reaction of RhCl3 with n-PrOH not only provides an active rhodium hydride species to catalyze isomerization of N-allyl amides to corresponding enamides but also generates a crucial catalytic amount of HCl to convert the enamides to deallylated amides through N,O-acetal exchange.

  DOI：

  10.1021/jo070553t
• 作为产物：
  描述：

  N-甲基烯丙基胺 、 3-氯苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-chloro-N-allyl-N-methyl-benzamide
  参考文献：
  名称：

  One-Step RhCl₃-Catalyzed Deprotection of Acyclic N-Allyl Amides

  摘要：

  [GRAPHICS]A convenient one-step RhCl3-catalyzed deprotection of acyclic N-allyl amides is described. Preliminary mechanistic studies reveal that the key to the success of the one-step deprotection process is the dual function of RhCl3 in alcohol solvents. Reaction of RhCl3 with n-PrOH not only provides an active rhodium hydride species to catalyze isomerization of N-allyl amides to corresponding enamides but also generates a crucial catalytic amount of HCl to convert the enamides to deallylated amides through N,O-acetal exchange.

  DOI：

  10.1021/jo070553t

文献信息

• Hydroxyalkylation-Initiated Radical Cyclization of <i>N</i>-Allylbenzamide for Direct Construction of Isoquinolinone
  作者：Wei Zhou、Shengyang Ni、Haibo Mei、Jianlin Han、Yi Pan

  DOI：10.1021/acs.orglett.5b01140

  日期：2015.6.5

  A metal-free hydroxyalkylation-initiated radical six-membered heterocycle formation reaction of N-allylbenzamide is developed. This reaction proceeds through C(sp(3))H bond cleavage, oxyalkylation of the double bond, and intramolecular cyclization, which provides a new route toward 4-substituted 3,4-dihydroisoquinolin-1(2H)-one derivatives.
• One-Step RhCl₃-Catalyzed Deprotection of Acyclic <i>N</i>-Allyl Amides
  作者：Michael J. Zacuto、Feng Xu

  DOI：10.1021/jo070553t

  日期：2007.8.1

  [GRAPHICS]A convenient one-step RhCl3-catalyzed deprotection of acyclic N-allyl amides is described. Preliminary mechanistic studies reveal that the key to the success of the one-step deprotection process is the dual function of RhCl3 in alcohol solvents. Reaction of RhCl3 with n-PrOH not only provides an active rhodium hydride species to catalyze isomerization of N-allyl amides to corresponding enamides but also generates a crucial catalytic amount of HCl to convert the enamides to deallylated amides through N,O-acetal exchange.