N-Pyrid-3-yl-triphenylphosphanimid | 104938-38-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-Pyrid-3-yl-triphenylphosphanimid
• 英文别名: Triphenyl(pyridin-3-ylimino)-lambda5-phosphane；triphenyl(pyridin-3-ylimino)-λ5-phosphane
• CAS: 104938-38-7
• 化学式: C₂₃H₁₉N₂P
• 分子量: 354.391
• InChiKey: BLRWTIOMPVXPQO-UHFFFAOYSA-N

物化性质

• 沸点：
  522.4±42.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Pyrid-3-yl-triphenylphosphanimid 以 xylene 为溶剂， 反应 14.0h， 生成 11-propyl-6H-indolo[2,3-b][1,5]naphthyridine
  参考文献：
  名称：

  Synthesis of 6H-Indolo[2,3-b][1,6]naphthyridines and Related Compounds as the 5-Aza Analogues of Ellipticine Alkaloids

  摘要：

  Treatment of 2-(1-alkynyl)phenyl isocyanates 6 with the iminophosphorane 14 produced in situ the benzoenynyl carbodiimides 15. Thermolysis of 15 under refluxing p-xylene furnished the 6H-indolo[2,3-b][1,6]naphthyridines 5, which could be regarded as the 5-aza analogues of ellipticine alkaloids. Similarly,condensation of 6 with the iminophosphorane 20 led to the formation of the 6H-indolo[2,3-b][1,5]naphthyridines 25 as the major isomer and the 10H- indolo[2,3-b][1,7]-naphthyridines 26 as the minor isomer. The indolonaphthyridines 32, 33, and 34 having a methoxyl substituent were likewise synthesized. Treatment of the diisocyanate 43 with 2 equiv of the iminophosphorane 7 furnished 45 having two indoloquinoline units incorporated in a seven-fused-ring system.

  DOI：

  10.1021/jo000978e
• 作为产物：
  描述：

  3-氨基吡啶 、 二溴三苯基膦 在 三乙胺 作用下， 以 苯 为溶剂， 反应 5.0h， 以76%的产率得到N-Pyrid-3-yl-triphenylphosphanimid
  参考文献：
  名称：

  Synthesis of 6H-Indolo[2,3-b][1,6]naphthyridines and Related Compounds as the 5-Aza Analogues of Ellipticine Alkaloids

  摘要：

  Treatment of 2-(1-alkynyl)phenyl isocyanates 6 with the iminophosphorane 14 produced in situ the benzoenynyl carbodiimides 15. Thermolysis of 15 under refluxing p-xylene furnished the 6H-indolo[2,3-b][1,6]naphthyridines 5, which could be regarded as the 5-aza analogues of ellipticine alkaloids. Similarly,condensation of 6 with the iminophosphorane 20 led to the formation of the 6H-indolo[2,3-b][1,5]naphthyridines 25 as the major isomer and the 10H- indolo[2,3-b][1,7]-naphthyridines 26 as the minor isomer. The indolonaphthyridines 32, 33, and 34 having a methoxyl substituent were likewise synthesized. Treatment of the diisocyanate 43 with 2 equiv of the iminophosphorane 7 furnished 45 having two indoloquinoline units incorporated in a seven-fused-ring system.

  DOI：

  10.1021/jo000978e

文献信息

• Base-mediated regioselective [3+2] annulation of ketenimines and isocyanides: efficient synthesis of 1,4,5-trisubstituted imidazoles
  作者：Jinxiong Cai、Haijie Bai、Yuan Wang、Xianxiu Xu、Haiming Xie、Jun Liu

  DOI：10.1039/c9cc01257e

  日期：——

  A novel base-mediated regioselective [3+2] annulation of active methylene isocyanides with ketenimines has been developed.

  已开发出一种新颖的以碱为媒介的活性甲基异氰酸酯与酮亚胺的[3+2]加成选择性反应。
• Electrosynthesis of Aryliminophosphoranes in Continuous Flow
  作者：Rodrigo Costa e Silva、Clara Vega、Morgan Regnier、Luca Capaldo、Lars Wesenberg、Grace Lowe、Kleber Thiago de Oliveira、Timothy Noël

  DOI：10.1002/adsc.202300635

  日期：2024.2.20

  Staudinger and Kirsanov reactions; C) This work. Despite the significant synthetic potential of iminophosphoranes, as of today, a safe and scalable method for their synthesis has not been established. Conventional approaches, such as the Staudinger and Kirsanov reactions, rely on the utilization of toxic and hazardous reagents like azides and molecular bromine (Scheme 1B). These conditions are unsustainable

  亚氨基正膦，也称为膦亚胺，作为多种有机化合物的重要前体，在合成化学领域具有巨大的潜力。它们与磷叶立德是等电子的，因此它们的化学性质非常相似。事实上，除了在交叉偶联或氢化反应中作为超碱1和配体的应用前景外， 2亚氨基正膦还可以作为通过氮杂维蒂希反应合成杂环、 3醛亚胺和酮亚胺、 4氮丙啶、5胺的便捷起始原料。 4、6和异氰酸酯通过 CO 2羰基化（方案 1A）。7 方案一 在图查看器中打开微软幻灯片软件 A) 亚氨基正膦作为合成中的通用中间体；B) 获得亚氨基正膦的常规方法：Staudinger 和 Kirsanov 反应；C) 这项工作。 尽管亚氨基正膦具有巨大的合成潜力，但迄今为止，尚未建立安全且可扩展的合成方法。施陶丁格反应和基尔萨诺夫反应等传统方法依赖于叠氮化物和分子溴等有毒有害试剂的使用（方案 1B）。这些条件是不可持续的，特别是考虑到从学术研究顺利过渡到工业规模生产的必要性时。
• Boedeker, J.; Koeckritz, A.; Koeckritz, P., Journal fur praktische Chemie (Leipzig 1954), 1985, vol. 327, # 5, p. 723 - 730
  作者：Boedeker, J.、Koeckritz, A.、Koeckritz, P.、Radeglia, R.

  DOI：——

  日期：——
• Synthesis of 6<i>H</i>-Indolo[2,3-<i>b</i>][1,6]naphthyridines and Related Compounds as the 5-Aza Analogues of Ellipticine Alkaloids
  作者：Quan Zhang、Chongsheng Shi、Hai-Ren Zhang、Kung K. Wang

  DOI：10.1021/jo000978e

  日期：2000.11.1

  Treatment of 2-(1-alkynyl)phenyl isocyanates 6 with the iminophosphorane 14 produced in situ the benzoenynyl carbodiimides 15. Thermolysis of 15 under refluxing p-xylene furnished the 6H-indolo[2,3-b][1,6]naphthyridines 5, which could be regarded as the 5-aza analogues of ellipticine alkaloids. Similarly,condensation of 6 with the iminophosphorane 20 led to the formation of the 6H-indolo[2,3-b][1,5]naphthyridines 25 as the major isomer and the 10H- indolo[2,3-b][1,7]-naphthyridines 26 as the minor isomer. The indolonaphthyridines 32, 33, and 34 having a methoxyl substituent were likewise synthesized. Treatment of the diisocyanate 43 with 2 equiv of the iminophosphorane 7 furnished 45 having two indoloquinoline units incorporated in a seven-fused-ring system.