N-(tert-butyldimethylsilyloxypropyl)-N-(3,4-dimethoxyphenyl)-α-carbomethoxyacetamide | 155257-33-3

• 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-(tert-butyldimethylsilyloxypropyl)-N-(3,4-dimethoxyphenyl)-α-carbomethoxyacetamide
• CAS: 155257-33-3
• 化学式: C₂₁H₃₅NO₆Si
• 分子量: 425.598
• InChiKey: BUFDJEARWWNUDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  29.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-(tert-butyldimethylsilyloxypropyl)-N-(3,4-dimethoxyphenyl)-α-carbomethoxyacetamide 在 Nafion-H 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 甲烷磺酰基叠氮化物 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 20.5h， 生成 1-(tert-butyldimethylsilyloxypropyl)-4,5-dimethoxy-2(3H)-indolinone
  参考文献：
  名称：

  The Nafion-H Catalysed Cyclization of α-Carbomethoxy-α-Diazoacetanilides. Synthesis of 3-Unsubstituted-2-Indolinones.

  摘要：

  Diazoanilides of type 4 were found to undergo Nafion-H catalysed cyclization onto the aromatic ring and concomitant decarboxylation, under optimal conditions, to give 3-unsubstituted 2-indolinones 5 in moderate yields. Diazoanilides that possess electron-donating substituents in the aromatic moiety gave higher yields of 5 and, in one case, the presence of an electron-withdrawing group in the aromatic moiety did not impede the cyclization. In the case of the diazoanilides that possess a N-butenyl group, preferential 1,3-dipolar cycloaddition of the diazo unit onto the butenyl double bond occurred to give an unstable 1-pyrazoline which was converted, by loss of nitrogen accompanied by hydrogen migration, to dihydro-2-pyridinone derivatives. It was also found that substituents ortho to the amido group and/or the site of cyclization sterically retarded the cyclization.

  DOI：

  10.1016/s0040-4020(01)80781-x
• 作为产物：
  描述：

  甲基丙二酸氢 、 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(tert-butyldimethylsilyloxypropyl)-N-(3,4-dimethoxyphenyl)-α-carbomethoxyacetamide
  参考文献：
  名称：

  The Nafion-H Catalysed Cyclization of α-Carbomethoxy-α-Diazoacetanilides. Synthesis of 3-Unsubstituted-2-Indolinones.

  摘要：

  Diazoanilides of type 4 were found to undergo Nafion-H catalysed cyclization onto the aromatic ring and concomitant decarboxylation, under optimal conditions, to give 3-unsubstituted 2-indolinones 5 in moderate yields. Diazoanilides that possess electron-donating substituents in the aromatic moiety gave higher yields of 5 and, in one case, the presence of an electron-withdrawing group in the aromatic moiety did not impede the cyclization. In the case of the diazoanilides that possess a N-butenyl group, preferential 1,3-dipolar cycloaddition of the diazo unit onto the butenyl double bond occurred to give an unstable 1-pyrazoline which was converted, by loss of nitrogen accompanied by hydrogen migration, to dihydro-2-pyridinone derivatives. It was also found that substituents ortho to the amido group and/or the site of cyclization sterically retarded the cyclization.

  DOI：

  10.1016/s0040-4020(01)80781-x

文献信息

• The Nafion-H Catalysed Cyclization of α-Carbomethoxy-α-Diazoacetanilides. Synthesis of 3-Unsubstituted-2-Indolinones.
  作者：Andrew G. Wee、Baosheng Liu

  DOI：10.1016/s0040-4020(01)80781-x

  日期：1994.1

  Diazoanilides of type 4 were found to undergo Nafion-H catalysed cyclization onto the aromatic ring and concomitant decarboxylation, under optimal conditions, to give 3-unsubstituted 2-indolinones 5 in moderate yields. Diazoanilides that possess electron-donating substituents in the aromatic moiety gave higher yields of 5 and, in one case, the presence of an electron-withdrawing group in the aromatic moiety did not impede the cyclization. In the case of the diazoanilides that possess a N-butenyl group, preferential 1,3-dipolar cycloaddition of the diazo unit onto the butenyl double bond occurred to give an unstable 1-pyrazoline which was converted, by loss of nitrogen accompanied by hydrogen migration, to dihydro-2-pyridinone derivatives. It was also found that substituents ortho to the amido group and/or the site of cyclization sterically retarded the cyclization.