7-benzoyl-7H-naphtho<2,3-b>carbazole-5,13-dione | 134513-42-1

• 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: 7-benzoyl-7H-naphtho<2,3-b>carbazole-5,13-dione
• 英文别名: 10-benzoyl-10-azapentacyclo[11.8.0.03,11.04,9.015,20]henicosa-1(13),2,4,6,8,11,15,17,19-nonaene-14,21-dione
• CAS: 134513-42-1
• 化学式: C₂₇H₁₅NO₃
• 分子量: 401.421
• InChiKey: QHXLSNCMKITTHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.26
• 重原子数：
  31.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.14
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1-benzoyl-2,3-bis(bromomethyl)indole 、 1,4-萘醌 在 sodium iodide 作用下， 生成 7-benzoyl-7H-naphtho<2,3-b>carbazole-5,13-dione
  参考文献：
  名称：

  N-benzoylindole-2,3-quinodimethane: Diels-Alder reactivity and synthetic applications for [b]annellated indoles

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)96104-6

文献信息

• New potential DNA intercalators of the carbazole series from indole-2,3-quinodimethanes: Synthesis, crystal structure, and molecular modeling with a watson-crick mini-helix
  作者：M. Dr�ger、M. Haber、H. Erfanian-Abdoust、U. Pindur、Kristin Sattler

  DOI：10.1007/bf00819524

  日期：1993.5

  1-Alkylpyrano[3,4-b]indol-3-ones 3 react via a Diels-Alder step with an aryne or N-phenylmaleimide to furnish the new [b]annellated carbazoles 4-10 in a one-pot process. In an analogous procedure, the in situ generated N-benzoylindole-2,3-quinodimethane (13) reacted with quinones to furnish the dioxocarbazoles 14-16. Compounds 4 8 and 14-16 with a coplanar skeleton are members of a class of potential DNA intercalators, as has been shown for 5 and 8 by X-ray structural analysis. On the basis of the geometries determined by X-ray crystallography, the intercalative binding of these molecules with a Watson-Crick mini-helix was predicted by molecular modeling methods,