N-benzyl-1-methyl-N-[2-[N-(trityloxy)ethanimidoyl]phenyl]-2,5-cyclohexadiene-1-carboxamide | 766512-24-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-benzyl-1-methyl-N-[2-[N-(trityloxy)ethanimidoyl]phenyl]-2,5-cyclohexadiene-1-carboxamide
• 英文别名: N-benzyl-1-methyl-N-[2-[(E)-C-methyl-N-trityloxycarbonimidoyl]phenyl]cyclohexa-2,5-diene-1-carboxamide
• CAS: 766512-24-7
• 化学式: C₄₂H₃₈N₂O₂
• 分子量: 602.776
• InChiKey: TZTIKZCRDZLJNE-FXLOMAGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  46
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyl-1-methyl-N-[2-[N-(trityloxy)ethanimidoyl]phenyl]-2,5-cyclohexadiene-1-carboxamide 在 过氧化双月桂酰 、 巯基乙酸甲酯 作用下， 以 苯 为溶剂， 反应 24.0h， 生成 1-benzyl-3-methyl-1,3-dihydro-2H-indol-2-one
  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：

  1-methylcyclohexa-2,5-diene-1-carboxylic acid 在 4-二甲氨基吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-benzyl-1-methyl-N-[2-[N-(trityloxy)ethanimidoyl]phenyl]-2,5-cyclohexadiene-1-carboxamide
  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.