methyl 9-phenylsulfonyl-9H-carbazole-2-carboxylate | 138054-42-9

• 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: methyl 9-phenylsulfonyl-9H-carbazole-2-carboxylate
• 英文别名: Methyl 9-(benzenesulfonyl)-9H-carbazole-2-carboxylate；methyl 9-(benzenesulfonyl)carbazole-2-carboxylate
• CAS: 138054-42-9
• 化学式: C₂₀H₁₅NO₄S
• 分子量: 365.409
• InChiKey: YRKFNDBFELNLEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-1-(Phenylsulfonyl)-3-(β-methoxyvinyl)indole 、 丙炔酸甲酯 在 4 A molecular sieve 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以12%的产率得到methyl 9-phenylsulfonyl-9H-carbazole-2-carboxylate
  参考文献：
  名称：

  New Diels-Alder Reactions of Oxy-functionalized 3-Vinylindoles with Carbodienophiles

  摘要：

  Some new Diels-Alder reactions of oxy-functionalized 3-vinylindoles (1, 2) with carbodienophiles are described. In most cases, functionalized carbazoles (4 - 6, 10 and 11) were formed regio- and/or endo-selectively, The product spectrum is characterized by [4 + 2] cycloadditions, elimination and ene reaction.

  DOI：

  10.3987/com-95-7235

文献信息

• New Diels-Alder reactions of (E/Z)-2'-methoxy-substituted 3-vinylindoles with carbo- and heterodienophiles: regio- and stereoselective access to [b]-annelated indoles and functionalized or [a]-annelated carbazoles
  作者：Ulf Pindur、Myung Hwa Kim、Martina Rogge、Werner Massa、Michel Molinier

  DOI：10.1021/jo00029a023

  日期：1992.1

  The (E/Z)-2'-methoxy-substituted 3-vinylindoles 1a,b react with some carbo- and azodienophiles to furnish new carbazoles and pyridazinoindoles. The conservation of the E and Z stereochemistry of 1 in these Diels-Alder reactions was investigated, and a mechanistic rationalization is given for the stereoselective and regioselective results observed.
• New Diels-Alder Reactions of Oxy-functionalized 3-Vinylindoles with Carbodienophiles
  作者：Ulf Pindur、Martina Rogge

  DOI：10.3987/com-95-7235

  日期：——

  Some new Diels-Alder reactions of oxy-functionalized 3-vinylindoles (1, 2) with carbodienophiles are described. In most cases, functionalized carbazoles (4 - 6, 10 and 11) were formed regio- and/or endo-selectively, The product spectrum is characterized by [4 + 2] cycloadditions, elimination and ene reaction.