diethyl 9-benzoyl-1,2,3,4-tetrahydro-9H-carbazole-2α,2β-dicarboxylate | 134513-50-1

• 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: diethyl 9-benzoyl-1,2,3,4-tetrahydro-9H-carbazole-2α,2β-dicarboxylate
• CAS: 134513-50-1
• 化学式: C₂₅H₂₅NO₅
• 分子量: 419.477
• InChiKey: PVRHFLIMNMAXPE-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  74.6
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  1-benzoyl-2,3-bis(bromomethyl)indole 、 富马酸二乙酯 在 4 A molecular sieve 、 sodium iodide 作用下， 反应 0.5h， 以63%的产率得到diethyl 9-benzoyl-1,2,3,4-tetrahydro-9H-carbazole-2α,2β-dicarboxylate
  参考文献：
  名称：

  Diels-Alder Reactions under Molecular Sieve Catalysis: Enhancement of Reactivity in Cyclization Reactions with N-Benzoylindole-2,3-quinodimethane to Functionalized Carbazoles

  摘要：

  In the presence of highly activated molecular sieves (4 A0), the Diels-Alder reactivity of in situ generated N-benzoylindole-2,3-quinodimethane is enhanced considerably. Reactions of this species with a variety of carbodienophiles give rise to novel functionalized and [b]annelated carbazole derivatives in a one-pot procedure.

  DOI：

  10.3987/com-91-5776

文献信息

• N-benzoylindole-2,3-quinodimethane: Diels-Alder reactivity and synthetic applications for [b]annellated indoles
  作者：Manfred Haber、Ulf Pindur

  DOI：10.1016/s0040-4020(01)96104-6

  日期：1991.3

  The Diels-Alder reactivity of in situ generated N-benzoylindole-2,3-quinodimethane has been expanded considerably to include reactions with carbon- and hetero-dienophiles which furnish a variety of [b]annellated indoles as well as functionalized and annellated carbazoles. The frontier molecular orbital theory was found to be a useful model for the prediction of the experimental results under consideration of reactivity aspects.