1,1'-Dimethoxy-3,3'-dimethyl-9H,9'H-[2,2']bicarbazolyl | 162119-02-0

• 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: 1,1'-Dimethoxy-3,3'-dimethyl-9H,9'H-[2,2']bicarbazolyl
• 英文别名: 1-methoxy-2-(1-methoxy-3-methyl-9H-carbazol-2-yl)-3-methyl-9H-carbazole
• CAS: 162119-02-0
• 化学式: C₂₈H₂₄N₂O₂
• 分子量: 420.511
• InChiKey: XQNYHMRUJRTQCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  50
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 dimeric O-demethylmurrayafoline A 以 乙醚 为溶剂， 反应 24.0h， 以76%的产率得到1,1'-Dimethoxy-3,3'-dimethyl-9H,9'H-[2,2']bicarbazolyl
  参考文献：
  名称：

  Dimeric Murrayafoline A, a potential Bis-Carbazole Alkaloid: 'Biomimetic' Synthesis, Atropoisomer Separation, and Antimalarial Activity

  摘要：

  The first total synthesis of a (potential) dimeric carbazole alkaloid is described. After an improved preparation of the monomeric building block, ''biomimetic dimerization'' by oxidative phenolic coupling was best achieved with di-terf-butyl peroxide in chlorobenzene, leading to a highly selective formation of the 2,2'-coupled ''dimer'', the parent framework of several naturally occurring dimeric carbazole alkaloids. For the atropo-enantiomer analysis, a chromatographic procedure on a chiral phase was developed. Both the mono- and the dimeric phenolic carbazoles displayed in vitro antimalarial activity against Plasmodium falciparum.

  DOI：

  10.3987/com-94-s30