N-[2-(trimethylsilyl)ethoxymethyl]-3-methyl-6-nitrocarbazol-1-ol | 863301-20-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-[2-(trimethylsilyl)ethoxymethyl]-3-methyl-6-nitrocarbazol-1-ol
• 英文别名: 3-Methyl-6-nitro-9-(2-trimethylsilylethoxymethyl)carbazol-1-ol
• CAS: 863301-20-6
• 化学式: C₁₉H₂₄N₂O₄Si
• 分子量: 372.496
• InChiKey: SRASAHTZECQLBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  80.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[2-(trimethylsilyl)ethoxymethyl]-3-methyl-6-nitrocarbazol-1-ol 在 tris(dibenzylideneacetone)dipalladium (0) NaBH₂S₃ 、 sodium hydride 、 sodium t-butanolate 、 2-(二环己基膦基)联苯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.0h， 生成 1',8-dimethoxy-3',6-dimethyl-9-[2-(trimethylsilyl)ethoxymethyl]-3,9'-bi-9H-carbazole
  参考文献：
  名称：

  Total Synthesis of Murrastifoline-A by Way of the Pd-catalyzed Double N-Arylation of a Carbazolamine with a 2,2’-Dibromobiphenyl Derivative

  摘要：

  DOI：

  10.3987/com-05-10418
• 作为产物：
  描述：

  N-[2-(trimethylsilyl)ethoxymethyl]-3-methyl-6-nitro-1-(4-toluenesulfonyloxy)carbazole 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以76%的产率得到N-[2-(trimethylsilyl)ethoxymethyl]-3-methyl-6-nitrocarbazol-1-ol
  参考文献：
  名称：

  One-step construction of carbazoles by way of the palladium-catalyzed double N-arylation reaction and its application to the total synthesis of murrastifoline-A

  摘要：

  The one-step construction of N-substituted carbazoles by way of the Pd-catalyzed double N-arylation reaction of primary amines with 2,2'-dibromobiphenyl is described. Aryl and aliphatic amines including tert-butylamine and a protected glucopyranosylamine were effectively transformed into the corresponding N-substituted carbazoles. The first total synthesis of murrastifoline-A, a biscarbazole alkaloid, based on this methodology is also presented. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.087

文献信息

• Total Synthesis of Murrastifoline-A by Way of the Pd-catalyzed Double N-Arylation of a Carbazolamine with a 2,2’-Dibromobiphenyl Derivative
  作者：Noritaka Chida、Takafumi Kitawaki、Yoko Hayashi

  DOI：10.3987/com-05-10418

  日期：——
• One-step construction of carbazoles by way of the palladium-catalyzed double N-arylation reaction and its application to the total synthesis of murrastifoline-A
  作者：Takafumi Kitawaki、Yoko Hayashi、Akiko Ueno、Noritaka Chida

  DOI：10.1016/j.tet.2006.04.087

  日期：2006.7

  The one-step construction of N-substituted carbazoles by way of the Pd-catalyzed double N-arylation reaction of primary amines with 2,2'-dibromobiphenyl is described. Aryl and aliphatic amines including tert-butylamine and a protected glucopyranosylamine were effectively transformed into the corresponding N-substituted carbazoles. The first total synthesis of murrastifoline-A, a biscarbazole alkaloid, based on this methodology is also presented. (c) 2006 Elsevier Ltd. All rights reserved.