3-(二苯基膦基)喹啉 | 1021148-68-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 3-(二苯基膦基)喹啉
• 英文名称: 3-diphenylphosphanequinoline
• 英文别名: 3-(diphenylphosphino)quinoline；Diphenyl(quinolin-3-yl)phosphane；diphenyl(quinolin-3-yl)phosphane
• CAS: 1021148-68-4
• 化学式: C₂₁H₁₆NP
• 分子量: 313.339
• InChiKey: HLOCLNAGFXKILN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  dichloro(cycloocta-1,5-diene)palladium (II) 、 3-(二苯基膦基)喹啉 以 二氯甲烷 为溶剂， 以63.9%的产率得到trans-di-μ-dichlorodibis(3-diphenylphosphanequinoline)di-palladium(II)
  参考文献：
  名称：

  Palladium(II) complexes of 2-, 3-, and 4-quinolinyl(diphenyl)phosphane and di-(3-quinolinyl)phenylphosphane: Synthesis, characterization, and catalytic screening

  摘要：

  One previously known and three novel quinolinyl phosphanes were synthesized by either a reaction between a lithiated diphenylphosphane and the appropriate chloroquinoline or by a reaction between a lithiated haloquinoline and an arylchlorophosphane. The reaction of the quinolinyl phenylphosphane ligands with PdCl2(cod) produced monomeric palladium complexes in diethyl ether and dimeric, chlorine-bridged complexes in dichloromethane. Crystal structures of the palladium complexes confirm that the quinolinyl phenylphosphanes do not form chelated structures while bonded to the metal centre. 2-Quinolinyl(diphenyl) phosphane has a tendency to form a cis-isomer while bonded to the metal centre in the mononuclear complex due to attractive interactions between two ligands. A catalytic study showed that the quinolinyl phenylphosphane ligands are moderately active in the Suzuki-Miyaura coupling of various aryl halides in air. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2007.09.009
• 作为产物：
  描述：

  3-溴喹啉 、 二苯基膦 在 potassium phosphate 、 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 作用下， 以 1,4-二氧六环 为溶剂， 以48%的产率得到diphenyl(quinolin-3-yl)phosphine oxide
  参考文献：
  名称：

  [NiCl2（dppp）]-芳基卤化物与亚磷酸二烷基酯，二苯膦氧化物和二苯膦的交叉偶联

  摘要：

  我们提出了一种通过使用[NiCl 2]使芳基卤化物与亚磷酸二烷基酯，二苯基氧化膦和二苯基膦交叉偶联形成CP键的一般方法。（dppp）]作为催化剂（dppp = 1,3-双（二苯基膦基）丙烷）。该催化剂体系具有广泛的适用性，能够催化芳基溴化物，特别是一系列未反应的芳基氯化物与各种类型的磷底物，如亚磷酸二烷基酯，二苯基氧化膦和二苯基膦的交叉偶联。因此，可以用一种催化剂体系实现有价值的膦酸酯，氧化膦和膦的合成。此外，该反应不仅在相对于经典Arbuzov反应（约160-220°C）低得多的温度（100-120°C）下进行，而且不需要外部还原剂和支持配体。另外，由于相对温和的反应条件，所以可以容忍一系列不稳定的基团，例如醚，酯，酮和氰基。最后，2（dppp）]作为催化剂，由于dppp配体的影响，Ni II中心很容易被磷底物原位还原成Ni 0，从而促进了芳基卤化物的氧化加成到Ni 0中心。该步骤是使反应进入催化循环的关键。

  DOI：

  10.1002/chem.201103723

文献信息

• [NiCl2(dppp)]-Catalyzed Cross-Coupling of Aryl Halides with Dialkyl Phosphite, Diphenylphosphine Oxide, and Diphenylphosphine
  作者：Yu-Long Zhao、Guo-Jie Wu、You Li、Lian-Xun Gao、Fu-She Han

  DOI：10.1002/chem.201103723

  日期：2012.7.27

  Consequently, the synthesis of valuable phosphonates, phosphine oxides, and phosphanes can be achieved with one catalyst system. Moreover, the reaction proceeds not only at a much lower temperature (100–120 °C) relative to the classic Arbuzov reaction (ca. 160–220 °C), but also without the need of external reductants and supporting ligands. In addition, owing to the relatively mild reaction conditions, a

  我们提出了一种通过使用[NiCl 2]使芳基卤化物与亚磷酸二烷基酯，二苯基氧化膦和二苯基膦交叉偶联形成CP键的一般方法。（dppp）]作为催化剂（dppp = 1,3-双（二苯基膦基）丙烷）。该催化剂体系具有广泛的适用性，能够催化芳基溴化物，特别是一系列未反应的芳基氯化物与各种类型的磷底物，如亚磷酸二烷基酯，二苯基氧化膦和二苯基膦的交叉偶联。因此，可以用一种催化剂体系实现有价值的膦酸酯，氧化膦和膦的合成。此外，该反应不仅在相对于经典Arbuzov反应（约160-220°C）低得多的温度（100-120°C）下进行，而且不需要外部还原剂和支持配体。另外，由于相对温和的反应条件，所以可以容忍一系列不稳定的基团，例如醚，酯，酮和氰基。最后，2（dppp）]作为催化剂，由于dppp配体的影响，Ni II中心很容易被磷底物原位还原成Ni 0，从而促进了芳基卤化物的氧化加成到Ni 0中心。该步骤是使反应进入催化循环的关键。
• Palladium(II) complexes of 2-, 3-, and 4-quinolinyl(diphenyl)phosphane and di-(3-quinolinyl)phenylphosphane: Synthesis, characterization, and catalytic screening
  作者：Juho Autio、Sauli Vuoti、M. Haukka、J. Pursiainen

  DOI：10.1016/j.ica.2007.09.009

  日期：2008.4

  One previously known and three novel quinolinyl phosphanes were synthesized by either a reaction between a lithiated diphenylphosphane and the appropriate chloroquinoline or by a reaction between a lithiated haloquinoline and an arylchlorophosphane. The reaction of the quinolinyl phenylphosphane ligands with PdCl2(cod) produced monomeric palladium complexes in diethyl ether and dimeric, chlorine-bridged complexes in dichloromethane. Crystal structures of the palladium complexes confirm that the quinolinyl phenylphosphanes do not form chelated structures while bonded to the metal centre. 2-Quinolinyl(diphenyl) phosphane has a tendency to form a cis-isomer while bonded to the metal centre in the mononuclear complex due to attractive interactions between two ligands. A catalytic study showed that the quinolinyl phenylphosphane ligands are moderately active in the Suzuki-Miyaura coupling of various aryl halides in air. (C) 2007 Elsevier B.V. All rights reserved.