N-methyl-N-(4-methoxyphenyl)-α-carbomethoxy-α-diazoacetamide | 148518-74-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-methyl-N-(4-methoxyphenyl)-α-carbomethoxy-α-diazoacetamide
• 英文别名: 2-Diazo-2-methoxycarbonyl-N-(4-methoxyphenyl)-N-methylethanamide；(Z)-2-diazonio-1-methoxy-3-(4-methoxy-N-methylanilino)-3-oxoprop-1-en-1-olate
• CAS: 148518-74-5
• 化学式: C₁₂H₁₃N₃O₄
• 分子量: 263.253
• InChiKey: KSJWMYZAEIVVHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-methyl-N-(4-methoxyphenyl)-α-carbomethoxy-α-diazoacetamide 在 Nafion-H 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以68%的产率得到1,3-二氢-5-甲氧基-1-甲基-2H-吲哚-2-酮
  参考文献：
  名称：

  Liu, Baosheng; Wee, Andrew G., Heterocycles, 1993, vol. 36, # 3, p. 445 - 448

  摘要：

  DOI：
• 作为产物：
  描述：

  N-methyl-N-(4-methoxyphenyl)-α-carbomethoxyacetamide 在 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 乙腈 为溶剂， 以53%的产率得到N-methyl-N-(4-methoxyphenyl)-α-carbomethoxy-α-diazoacetamide
  参考文献：
  名称：

  Effects of catalysts on the cyclization of 2-diazo-2-methoxycarbonyl-N-aryl-N-alkylethanamides

  摘要：

  无机固体对标题化合物分解产物的分布有明显的影响；沸石 Kβ 对指导吲哚啉酮类化合物的合成特别有用，如 5-甲氧基-N-甲基吲哚啉-2-酮，它是由 2-重氮-2-甲氧基羰基-N-（4-甲氧基苯基）-N-甲基乙酰胺生成的，产率为 89%；对其可能的机理进行了推测。

  DOI：

  10.1039/p19960002793

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.
• Effects of catalysts on the cyclization of 2-diazo-2-methoxycarbonyl-N-aryl-N-alkylethanamides
  作者：Keith Smith、Dawoud Bahzad

  DOI：10.1039/p19960002793

  日期：——

  Inorganic solids have pronounced effects on the product distribution from decomposition of the title compounds; zeolite Kβ is particularly useful for directing the synthesis of indolinones such as 5-methoxy-N-methylindolin-2-one, which is formed in 89% yield from 2-diazo-2-methoxycarbonyl-N-(4-methoxyphenyl)-N-methylethanamide; speculation is made about a possible mechanism.

  无机固体对标题化合物分解产物的分布有明显的影响；沸石 Kβ 对指导吲哚啉酮类化合物的合成特别有用，如 5-甲氧基-N-甲基吲哚啉-2-酮，它是由 2-重氮-2-甲氧基羰基-N-（4-甲氧基苯基）-N-甲基乙酰胺生成的，产率为 89%；对其可能的机理进行了推测。
• Liu, Baosheng; Wee, Andrew G., Heterocycles, 1993, vol. 36, # 3, p. 445 - 448
  作者：Liu, Baosheng、Wee, Andrew G.

  DOI：——

  日期：——