4-diazo-3-methyl-5--4,7-dihydroindol-7-one | 133471-88-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-diazo-3-methyl-5--4,7-dihydroindol-7-one
• CAS: 133471-88-2
• 化学式: C₁₄H₁₄N₄O₂
• 分子量: 270.291
• InChiKey: ADPVLVLGCCVOOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  89.57
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-diazo-3-methyl-5--4,7-dihydroindol-7-one 在 trifluoropentanedionatocopper(I) carbonyl-n-butylamine 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以36%的产率得到6-乙酰基-3-甲基-4,4a,5,6-四氢环丙烯并[c]吡咯并[3,2-e]吲哚-8(1H)-酮
  参考文献：
  名称：

  Synthesis of cycloprop[c]indol-5-ones from 4-diazo-3-[n-(2-propenyl)amido]cyclohexadien-1-ones. Exploration of copper(I) and copper(II) complexes as catalysts

  摘要：

  The cyclization of 4-diazo-3-[N-(2-propenyl)amido]cyclohexadienones to cycloprop[c]indol-5-ones under the influence of copper(I) and copper(II) compounds has been investigated. Catalysis is observed with copper(I) triflate, the carbon monoxide complex of copper(I) triflate, and the carbon monoxide complexes of trifluoropentanedionato- and hexafluoropentanedionatocopper(I). The best results, essentially quantitative conversion, are achieved with a catalyst solution containing trifluoropentanedionatocopper(I) carbonyl and 1 equiv of n-butylamine. No significant enantioselectivity is observed with a chiral salicyliminatocopper(II), [(trifluoroacetyl)camphorato]copper(I) carbonyl, or a trifluoropentanedionatocopper(I) carbonyl solution containing (S)-alpha-naphthylethylamine. A mechanistic interpretation involving reductive dediazonization, exo-trig radical cyclization, and cyclopropane formation by the resulting intermediate is proposed.

  DOI：

  10.1021/jo00009a023
• 作为产物：
  描述：

  1-(benzenesulfonyl)-3-methyl-7-phenylmethoxyindol-5-amine 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 硝酸铵 、 三溴化硼 、 sodium hydride 、 三氟乙酸酐 、 环己烯 、 亚硝酸异戊酯 作用下， 以 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 49.92h， 生成 4-diazo-3-methyl-5--4,7-dihydroindol-7-one
  参考文献：
  名称：

  Synthesis of cycloprop[c]indol-5-ones from 4-diazo-3-[n-(2-propenyl)amido]cyclohexadien-1-ones. Exploration of copper(I) and copper(II) complexes as catalysts

  摘要：

  The cyclization of 4-diazo-3-[N-(2-propenyl)amido]cyclohexadienones to cycloprop[c]indol-5-ones under the influence of copper(I) and copper(II) compounds has been investigated. Catalysis is observed with copper(I) triflate, the carbon monoxide complex of copper(I) triflate, and the carbon monoxide complexes of trifluoropentanedionato- and hexafluoropentanedionatocopper(I). The best results, essentially quantitative conversion, are achieved with a catalyst solution containing trifluoropentanedionatocopper(I) carbonyl and 1 equiv of n-butylamine. No significant enantioselectivity is observed with a chiral salicyliminatocopper(II), [(trifluoroacetyl)camphorato]copper(I) carbonyl, or a trifluoropentanedionatocopper(I) carbonyl solution containing (S)-alpha-naphthylethylamine. A mechanistic interpretation involving reductive dediazonization, exo-trig radical cyclization, and cyclopropane formation by the resulting intermediate is proposed.

  DOI：

  10.1021/jo00009a023