4-Methyl-2-phenyl-10,10a-dihydro-1H,3H,5H-pyrrolo<3,4-b>carbazole-1,3-dione | 142818-10-8

• 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: 4-Methyl-2-phenyl-10,10a-dihydro-1H,3H,5H-pyrrolo<3,4-b>carbazole-1,3-dione
• 英文别名: 10-methyl-2-phenyl-4,9-dihydro-3aH-pyrrolo[3,4-b]carbazole-1,3-dione
• CAS: 142818-10-8
• 化学式: C₂₁H₁₆N₂O₂
• 分子量: 328.37
• InChiKey: BZBXUFZKKOMGGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  53.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  N-苯基马来酰亚胺 、 1-甲基-9H-吡喃并[3,4-b]吲哚-3-酮 以 various solvent(s) 为溶剂， 反应 13.0h， 生成 4-Methyl-2-phenyl-1H,3H,5H-pyrrolo<3,4-b>carbazole-1,3-dione 、 4-Methyl-2-phenyl-10,10a-dihydro-1H,3H,5H-pyrrolo<3,4-b>carbazole-1,3-dione 、 2,14-Diphenyl-4-methyl-3a,5,10,10a-tetrahydro(3acH,10acH,11synH)-4t,10t-epipyrrolopyrrolo<3,4-b>carbazole-1,3,13,15-tetraone
  参考文献：
  名称：

  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

  摘要：

  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,

  DOI：

  10.1007/bf00819524

文献信息

• A One-Pot Access to [b]Annellated Carbazoles as Potential DNA Intercalators via Diels-Alder Reactions with 1-Alkylpyrano[3,4-b]indol-3-ones
  作者：Ulf Pindur、Manfred Haber、Houshang Erfanian-Abdoust

  DOI：10.3987/com-91-5964

  日期：——

  1-Alkylpyrano[3,4-b]indol-3-ones (3) react via a Diels-Alder process with arynes or N-phenylmaleimide to furnish [b]annellated carbazoles (4-10) in a one-pot procedure. Compounds (4-8) with a coplanar framework belong to the class of potential DNA intercalators.
• 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,