5-acetamido-6-(bromomethyl)-6-hydroxy-1-(methanesulfonyl)-2,3-dihydroindole | 133471-91-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-acetamido-6-(bromomethyl)-6-hydroxy-1-(methanesulfonyl)-2,3-dihydroindole
• 英文别名: N-[3-(bromomethyl)-6-hydroxy-1-methylsulfonyl-2,3-dihydroindol-5-yl]acetamide
• CAS: 133471-91-7
• 化学式: C₁₂H₁₅BrN₂O₄S
• 分子量: 363.232
• InChiKey: GFKBBLCMXLROHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  95.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-acetamido-6-(bromomethyl)-6-hydroxy-1-(methanesulfonyl)-2,3-dihydroindole 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到N-(3-Methanesulfonyl-5-oxo-1a,2,3,5-tetrahydro-1H-3-aza-cyclopropa[c]inden-6-yl)-acetamide
  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：

  2-acetamido-5--4-diazocyclohexadienone 在 copper(ll) bromide 作用下， 以 二甲基亚砜 为溶剂， 以54%的产率得到5-acetamido-6-(bromomethyl)-6-hydroxy-1-(methanesulfonyl)-2,3-dihydroindole
  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：——