1-(diphenylphosphino)-1H-indole

• 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-(diphenylphosphino)-1H-indole
• 英文别名: 1-(diphenylphosphonyl)indole；N-indolyldiphenylphosphine；Indol-1-yl(diphenyl)phosphane
• 化学式: C₂₀H₁₆NP
• 分子量: 301.327
• InChiKey: NYVCELZNDJLQCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  吲哚 、 二苯基氯化膦 在 三乙胺 作用下， 以 乙醚 为溶剂， 以39.7%的产率得到1-(diphenylphosphino)-1H-indole
  参考文献：
  名称：

  Gurevich, P. A.; RAzumov, A. I.; Komina, T. V., Journal of general chemistry of the USSR, 1985, vol. 55, # 5, p. 1121 - 1125

  摘要：

  DOI：

文献信息

• Electrochemical oxidative N–H/P–H cross-coupling with H₂ evolution towards the synthesis of tertiary phosphines
  作者：Yong Yuan、Xue Liu、Jingcheng Hu、Pengjie Wang、Shengchun Wang、Hesham Alhumade、Aiwen Lei

  DOI：10.1039/d1sc07248j

  日期：——

  Tertiary phosphines(III) find widespread use in many aspects of synthetic organic chemistry. Herein, we developed a facile and novel electrochemical oxidative N–H/P–H cross-coupling method, leading to a series of expected tertiary phosphines(III) under mild conditions with excellent yields. It is worth noting that this electrochemical protocol features very good reaction selectivity, where only a 1 : 1

  叔膦( III )在合成有机化学的许多方面都有广泛的用途。在此，我们开发了一种简便且新颖的电化学氧化N-H/P-H交叉偶联方法，在温和的条件下以优异的产率产生了一系列预期的叔膦( III )。值得注意的是，该电化学方案具有非常好的反应选择性，反应中仅需要胺和磷化氢的比例为1:1。此外，该电化学协议被证明是实用且可扩展的。机理分析表明 P 自由基参与了该反应。
• 3-Indolylphosphines as ligand for palladium in Suzuki–Miyaura coupling reaction of chloroarenes: substituent effects
  作者：Debajyoti Saha、Raju Ghosh、Amitabha Sarkar

  DOI：10.1016/j.tet.2013.03.030

  日期：2013.5

  The ligand 1,3-bis(diphenylphosphino)-1H-indole, L1 with palladium promotes Suzuki-Miyaura coupling reaction of chloroarenes and benzyl chlorides with arylboronic acids. Structural modification of L1 established that the phosphine group at C-3 position of indole was crucial to catalysis and its efficacy depended on the nature of the N-substituent. P-31 chemical shift values of the substituted indolylphosphines appear to show a correlation with observed trend in catalytic efficiency. (C) 2013 Elsevier Ltd. All rights reserved.
• Selective Ethylene Tri-/Tetramerization by in Situ-Formed Chromium Catalysts Stabilized by N,P-Based Ancillary Ligand Systems
  作者：Yun Yang、Zhen Liu、Boping Liu、Robbert Duchateau

  DOI：10.1021/cs4004968

  日期：2013.10.4

  A series of N,P-based ancillary ligands have been synthesized, and the corresponding catalysts, formed in situ by mixing one of the N,P-ligands, Cr(acac)(3) and MAO, have been tested for ethylene oligomerization. Under standard ethylene oligomerization conditions (30 bar ethylene, 60 degrees C, methylcyclohexane solvent), all of the in situ formed complexes show catalytic activity, producing oligomers together with varying amounts of polyethylene (PE). Of all these combinations, only the catalyst formed by mixing N-pyrrolyldiphenylphosphine with Cr(acac)(3) and MAO is capable of selectively oligomerizing ethylene, producing a mixture of 1-hexene and 1-octene in varying ratios alongside a small amount of PE. Further investigations on this catalyst system revealed that the presence of a low concentration of toluene favors the production of 1-octene. However, in pure toluene as the solvent, the selectivity toward 1-hexene/1-octene is lost and a statistic mixture of alpha-olefins is produced. Moreover, the choice of the cocatalyst is to dramatically influence the composition of the liquid products. By careful adjustment of the reaction conditions (temperature, ethylene pressure, catalyst loading, and ligand/Cr ratio), the 1-hexene/1-octene molar ratio can be tuned from 0.3 to 20 and a selectivity for 1-octene formation of up to 74% can be achieved.
• Synthesis of Pyrrolyl-, Indolyl-, and Carbazolylphosphanes and Their Catalytic Application as Ligands in the Hydroformylation of 2-Pentene
  作者：Ralf Jackstell、Holger Klein、Matthias Beller、Klaus-Diether Wiese、Dirk Röttger

  DOI：10.1002/1099-0690(200110)2001:20<3871::aid-ejoc3871>3.0.co;2-v

  日期：2001.10
• GUREVICH, P. A.;RAZUMOV, A. I.;KOMINA, T. V.;KLIMENTOVA, G. YU.;ZYKOVA, T+, ZH. OBSHCH. XIMII, 1985, 55, N 6, 1257-1262
  作者：GUREVICH, P. A.、RAZUMOV, A. I.、KOMINA, T. V.、KLIMENTOVA, G. YU.、ZYKOVA, T+

  DOI：——

  日期：——