6-methoxy-2,3-dimethyl-1H-benzo[g]indole | 1093167-90-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-methoxy-2,3-dimethyl-1H-benzo[g]indole
• CAS: 1093167-90-8
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: YMTFGAPECFSCFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-甲氧基-1-萘胺 、 2,3-丁二醇 在 iridium (III) chloride trihydrate 、 氧气 、 sodium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 均三甲苯 为溶剂， 169.0 ℃ 、101.33 kPa 条件下， 反应 15.0h， 以76%的产率得到6-methoxy-2,3-dimethyl-1H-benzo[g]indole
  参考文献：
  名称：

  N-Heterocyclization of Naphthylamines with 1,2- and 1,3-Diols Catalyzed by an Iridium Chloride/BINAP System

  摘要：

  Benzoquinoline derivatives were successfully synthesized by iridium-catalyzed N-heterocyclization of naphthylamines with diols. For instance, the reaction of 1-naphthylamine with 1,3-propanediol catalyzed by IrCl3 combined with BINAP as a ligand produced 7,8-benzoquinoline in quantitative yield. The N-heterocyclization reaction was found to be markedly influenced by the ligands employed. Benzoindoles were also synthesized by the same strategy from napthylamines with 1,2-diols. A reaction mechanism for the N-heterocyclization of naphthylamines with 1,3-diols by IrCl3 was proposed.

  DOI：

  10.1021/jo801966u

文献信息

• <i>N</i>-Heterocyclization of Naphthylamines with 1,2- and 1,3-Diols Catalyzed by an Iridium Chloride/BINAP System
  作者：Hiroomi Aramoto、Yasushi Obora、Yasutaka Ishii

  DOI：10.1021/jo801966u

  日期：2009.1.16

  Benzoquinoline derivatives were successfully synthesized by iridium-catalyzed N-heterocyclization of naphthylamines with diols. For instance, the reaction of 1-naphthylamine with 1,3-propanediol catalyzed by IrCl3 combined with BINAP as a ligand produced 7,8-benzoquinoline in quantitative yield. The N-heterocyclization reaction was found to be markedly influenced by the ligands employed. Benzoindoles were also synthesized by the same strategy from napthylamines with 1,2-diols. A reaction mechanism for the N-heterocyclization of naphthylamines with 1,3-diols by IrCl3 was proposed.