N-(naphthalen-1-yl)-N'-phenylpropane-1,3-diamine | 1093167-92-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(naphthalen-1-yl)-N'-phenylpropane-1,3-diamine
• 英文别名: N'-naphthalen-1-yl-N-phenylpropane-1,3-diamine
• CAS: 1093167-92-0
• 化学式: C₁₉H₂₀N₂
• 分子量: 276.381
• InChiKey: ZJBOIOTXCCOLDG-UHFFFAOYSA-N

物化性质

• 沸点：
  502.7±33.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(naphthalen-1-yl)-N'-phenylpropane-1,3-diamine 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， 反应 15.0h， 以69%的产率得到7,8-苯并喹啉
  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
• 作为产物：
  描述：

  3-苯胺-1-丙醇 、 1-萘胺 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， 反应 15.0h， 以33%的产率得到N-(naphthalen-1-yl)-N'-phenylpropane-1,3-diamine
  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

• Substituierte Tetrahydropyrimidinonderivate, Verfahren zu ihrer Herstellung und Herbizide, die diese Derivate als Wirkstoffe enthalten
  申请人：NIHON TOKUSHU NOYAKU SEIZO K.K.

  公开号：EP0058868A1

  公开（公告）日：1982-09-01

  Die Erfindung betrifft neue substituierte Tetrahydropyrimidinon-Derivate der allgemeinen Formel worin die Gruppen Ar gleich oder verschieden sein können und jeweils die in der Beschreibung angegebene Bedeutung besitzen, mehrere Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide.

  本发明涉及通式中的新的取代的四氢嘧啶酮衍生物，通式中的基团 Ar 可以相同或不同，各自具有描述中给出的含义，本发明还涉及其制备的几种工艺及其作为除草剂的用途。
• US4402731A
  申请人：——

  公开号：US4402731A

  公开（公告）日：1983-09-06
• <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.