7-(benzyloxy)-5-(methanesulfonamido)-3-methyl-1-(phenylsulfonyl)indole | 133471-82-6

• 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: 7-(benzyloxy)-5-(methanesulfonamido)-3-methyl-1-(phenylsulfonyl)indole
• 英文别名: Methanesulfonamide, N-[3-methyl-7-(phenylmethoxy)-1-(phenylsulfonyl)-1H-indol-5-yl]-；N-[1-(benzenesulfonyl)-3-methyl-7-phenylmethoxyindol-5-yl]methanesulfonamide
• CAS: 133471-82-6
• 化学式: C₂₃H₂₂N₂O₅S₂
• 分子量: 470.57
• InChiKey: QCTIOGQIHRSREV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-(benzyloxy)-5-(methanesulfonamido)-3-methyl-1-(phenylsulfonyl)indole 、 3-溴丙烯 在 potassium tert-butylate 作用下， 生成 7-(benzyloxy)-3-methyl-1-(phenylsulfonyl)-5-indole
  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：

  7-(苄氧基)-3-甲基-5-硝基-1H-吲哚 在 吡啶 、 sodium hydride 、 calcium chloride 、 锌 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 5.5h， 生成 7-(benzyloxy)-5-(methanesulfonamido)-3-methyl-1-(phenylsulfonyl)indole
  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

文献信息

• SUNDBERG, RICHARD J.;PITTS, WILLIAM J., J. ORG. CHEM., 56,(1991) N, C. 3048-3054
  作者：SUNDBERG, RICHARD J.、PITTS, WILLIAM J.

  DOI：——

  日期：——
• 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
  作者：Richard J. Sundberg、William J. Pitts

  DOI：10.1021/jo00009a023

  日期：1991.4

  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.