1,4,11,14-tetramethyl-5,10-dihydro-carbazolo[3,4-c]carbazole | 174786-87-9

• 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: 1,4,11,14-tetramethyl-5,10-dihydro-carbazolo[3,4-c]carbazole
• 英文别名: (-)-1,4,11,14-tetramethyl-5,10-dihydro-carbazolo[3,4-c]carbazole；(+)-1,4,11,14-tetramethyl-5,10-dihydro-carbazolo[3,4-c]carbazole
• CAS: 174786-87-9
• 化学式: C₂₆H₂₂N₂
• 分子量: 362.474
• InChiKey: KJHLSEGENJPZAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.34
• 重原子数：
  28.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  31.58
• 氢给体数：
  2.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  2,5-二甲基苯肼盐酸盐 在 sodium dithionite 作用下， 生成 1,4,11,14-tetramethyl-5,10-dihydro-carbazolo[3,4-c]carbazole
  参考文献：
  名称：

  A configurationally stable pyrrolohelicene: experimental and theoretical structure-chiroptic relationships

  摘要：

  The sterically overcrowded tetramethyldipyrrolo[6]helicene 2 was prepared by the Bucherer reaction for the first time. While the longest known hexahelicene 1 does not form stable enantiomers at room temperature, 2 could be separated into the antipodes, which is explained by the extremely different racemization barriers of the two compounds (approximate to 60 kJ/mol for 1, and approximate to 195 kJ/mol for 2). The quantum mechanically calculated and experimentally determined geometries are in good accordance. The strongly deformed helix 2 shows a pitch enlarged by 62 pm compared to the non-substituted compound 1. Whereas 1 forms intermolecular hydrogen bonds in the solid, the crystal structure of 2 exhibits coordination of clathrated acetone at the NH-groups. Experimental and theoretically simulated CD Spectra of 2 are compared.

  DOI：

  10.1016/0957-4166(95)00427-0

文献信息

• A configurationally stable pyrrolohelicene: experimental and theoretical structure-chiroptic relationships
  作者：Ivo Pischel、Stefan Grimme、Sirpa Kotila、Martin Nieger、Fritz Vögtle

  DOI：10.1016/0957-4166(95)00427-0

  日期：1996.1

  The sterically overcrowded tetramethyldipyrrolo[6]helicene 2 was prepared by the Bucherer reaction for the first time. While the longest known hexahelicene 1 does not form stable enantiomers at room temperature, 2 could be separated into the antipodes, which is explained by the extremely different racemization barriers of the two compounds (approximate to 60 kJ/mol for 1, and approximate to 195 kJ/mol for 2). The quantum mechanically calculated and experimentally determined geometries are in good accordance. The strongly deformed helix 2 shows a pitch enlarged by 62 pm compared to the non-substituted compound 1. Whereas 1 forms intermolecular hydrogen bonds in the solid, the crystal structure of 2 exhibits coordination of clathrated acetone at the NH-groups. Experimental and theoretically simulated CD Spectra of 2 are compared.