3-methyl-6-nitro-1-(4-toluenesulfonyloxy)carbazole | 863301-18-2

• 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: 3-methyl-6-nitro-1-(4-toluenesulfonyloxy)carbazole
• 英文别名: (3-methyl-6-nitro-9H-carbazol-1-yl) 4-methylbenzenesulfonate
• CAS: 863301-18-2
• 化学式: C₂₀H₁₆N₂O₅S
• 分子量: 396.423
• InChiKey: RYQPDLWUZJAEQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-methyl-6-nitro-1-(4-toluenesulfonyloxy)carbazole 在 sodium hydroxide 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[2-(trimethylsilyl)ethoxymethyl]-3-methyl-6-nitrocarbazol-1-ol
  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：

  4-toluenesulfonic acid 5-methyl-2-[(4-nitrophenyl)amino]phenyl ester 在 palladium diacetate 、 溶剂黄146 作用下， 反应 5.0h， 以53%的产率得到3-methyl-6-nitro-1-(4-toluenesulfonyloxy)carbazole
  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.