(2-acetyl-4,5-dimethoxyphenyl)benzylamonium chloride

• 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: (2-acetyl-4,5-dimethoxyphenyl)benzylamonium chloride
• 英文别名: 1-[2-(Benzylamino)-4,5-dimethoxyphenyl]ethanone;hydrochloride
• 化学式: C₁₇H₁₉NO₃*ClH
• 分子量: 321.804
• InChiKey: AMTYLOLYHKQQNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  22
• 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：
  47.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-acetyl-4,5-dimethoxyphenyl)benzylamonium chloride 在 4-二甲氨基吡啶 、 二叔丁基过氧化物 、 硫酸 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Approach to 3-Aminoindolin-2-ones via Oxime Ether Functionalized Carbamoylcyclohexadienes

  摘要：

  O-Benzyloxime ether substituted amidocyclohexadienes were prepared in three steps in good yields from 2-aminoacetophenone. EPR spectroscopic observations and product analyses showed that peroxide-induced decompositions of model compounds led to indolin-2-ones with benzyloxyaminyl substitution at their 3-positions. The cyclization steps were very rapid and took place regioselectively at the C-atoms of the C=N bonds, by 5-exo ring closures. An O-trityloxime ether analogue was also prepared. The cyclohexadienyl intermediate smoothly yielded an alkoxylaminyl radical again by rapid 5-exo-cyclization. However, ring closure was quickly followed by another beta-scission step that released the persistent trityl radical and a 3-nitrosoindolin-2-one derivative. EPR spectroscopic evidence showed that the nitroso compound trapped other transient intermediates to afford a series of nitroxides. GC-MS analyses of products formed in reactions including methyl thioglycolate indicated that 1-benzyl-3-methyl-1,3-dihydro-2H-indol-2-one was derived from the indolinone moiety.

  DOI：

  10.1021/jo049617f
• 作为产物：
  描述：

  溴甲苯 、 2'-氨基-4',5'-二甲氧基苯乙酮 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以70%的产率得到(2-acetyl-4,5-dimethoxyphenyl)benzylamonium chloride
  参考文献：
  名称：

  Approach to 3-Aminoindolin-2-ones via Oxime Ether Functionalized Carbamoylcyclohexadienes

  摘要：

  O-Benzyloxime ether substituted amidocyclohexadienes were prepared in three steps in good yields from 2-aminoacetophenone. EPR spectroscopic observations and product analyses showed that peroxide-induced decompositions of model compounds led to indolin-2-ones with benzyloxyaminyl substitution at their 3-positions. The cyclization steps were very rapid and took place regioselectively at the C-atoms of the C=N bonds, by 5-exo ring closures. An O-trityloxime ether analogue was also prepared. The cyclohexadienyl intermediate smoothly yielded an alkoxylaminyl radical again by rapid 5-exo-cyclization. However, ring closure was quickly followed by another beta-scission step that released the persistent trityl radical and a 3-nitrosoindolin-2-one derivative. EPR spectroscopic evidence showed that the nitroso compound trapped other transient intermediates to afford a series of nitroxides. GC-MS analyses of products formed in reactions including methyl thioglycolate indicated that 1-benzyl-3-methyl-1,3-dihydro-2H-indol-2-one was derived from the indolinone moiety.

  DOI：

  10.1021/jo049617f

文献信息

• Approach to 3-Aminoindolin-2-ones via Oxime Ether Functionalized Carbamoylcyclohexadienes
  作者：A. Franco Bella、Alexandra M. Z. Slawin、John C. Walton

  DOI：10.1021/jo049617f

  日期：2004.9.1

  O-Benzyloxime ether substituted amidocyclohexadienes were prepared in three steps in good yields from 2-aminoacetophenone. EPR spectroscopic observations and product analyses showed that peroxide-induced decompositions of model compounds led to indolin-2-ones with benzyloxyaminyl substitution at their 3-positions. The cyclization steps were very rapid and took place regioselectively at the C-atoms of the C=N bonds, by 5-exo ring closures. An O-trityloxime ether analogue was also prepared. The cyclohexadienyl intermediate smoothly yielded an alkoxylaminyl radical again by rapid 5-exo-cyclization. However, ring closure was quickly followed by another beta-scission step that released the persistent trityl radical and a 3-nitrosoindolin-2-one derivative. EPR spectroscopic evidence showed that the nitroso compound trapped other transient intermediates to afford a series of nitroxides. GC-MS analyses of products formed in reactions including methyl thioglycolate indicated that 1-benzyl-3-methyl-1,3-dihydro-2H-indol-2-one was derived from the indolinone moiety.