1-(3-(二苯基膦基)苯基)乙酮 | 50777-60-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(3-(二苯基膦基)苯基)乙酮
• 英文名称: (m-Acetylphenyl)(diphenyl)phosphin
• 英文别名: (3-Acetylphenyl)diphenyl phosphane；1-(3-diphenylphosphanylphenyl)ethanone
• CAS: 50777-60-1
• 化学式: C₂₀H₁₇OP
• 分子量: 304.328
• InChiKey: TZCYOOPGOMPVBQ-UHFFFAOYSA-N

物化性质

• 熔点：
  85-86 °C
• 沸点：
  432.1±28.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-(二苯基膦基)苯基)乙酮 在 双氧水 、 一水合肼 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 7.0h， 生成 [3-(3-pyrazolyl)phenyl]diphenylphosphane oxide
  参考文献：
  名称：

  Novel phosphine ligands bearing 3(5)-pyrazolyl and 4-(2-amino)pyrimidinyl groups: Synthesis and coordination chemistry

  摘要：

  Novel triphenyl phosphine ligands bearing pyrazole or 2-aminopyrimidine groups in the ortho or meta position of one or three of the phenyl rings were obtained starting from the corresponding acyl derivatives Ph2P(o-C6H4-COCH3), Ph2P(m-C6H4-COCH3), Or P(m-C6H4-COCH3)(3)- Conversion of the acyl groups into 3-dimethylamino-2-propen-l-onyl units was achieved by reaction with HC(O-Me)(2)NMe2 which underwent ring closing with hydrazine or guanidine to yield the desired heterocycles. Two palladium complexes were synthesized using the coordinatively labile precursor (PhCN)(2)PdCl2, one of them could be characterized by X-ray structure analysis. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.08.032
• 作为产物：
  描述：

  2-(3-溴苯基)-2-甲基-1,3-二氧戊环 在 对甲苯磺酸 、 magnesium 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 1-(3-(二苯基膦基)苯基)乙酮
  参考文献：
  名称：

  Novel phosphine ligands bearing 3(5)-pyrazolyl and 4-(2-amino)pyrimidinyl groups: Synthesis and coordination chemistry

  摘要：

  Novel triphenyl phosphine ligands bearing pyrazole or 2-aminopyrimidine groups in the ortho or meta position of one or three of the phenyl rings were obtained starting from the corresponding acyl derivatives Ph2P(o-C6H4-COCH3), Ph2P(m-C6H4-COCH3), Or P(m-C6H4-COCH3)(3)- Conversion of the acyl groups into 3-dimethylamino-2-propen-l-onyl units was achieved by reaction with HC(O-Me)(2)NMe2 which underwent ring closing with hydrazine or guanidine to yield the desired heterocycles. Two palladium complexes were synthesized using the coordinatively labile precursor (PhCN)(2)PdCl2, one of them could be characterized by X-ray structure analysis. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.08.032

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。
• Synthesis of aryl phosphines via phosphination with triphenylphosphine by supported palladium catalysts
  作者：Yanchun Wang、Chi Wai Lai、Fuk Yee Kwong、Wen Jia、Kin Shing Chan

  DOI：10.1016/j.tet.2004.08.020

  日期：2004.10

  The palladium catalyzed phosphination of functionalized aryl bromides, triflates, and chlorides with triphenylphosphine to yield aryldiphenylphosphines was catalyzed by thermally stable palladium catalysts supported on charcoal and aluminia. The addition of NaI promoted both the rates and yields in the phosphination with Pd/C.

  木炭和氧化铝上负载的热稳定钯催化剂催化钯催化的功能化芳基溴化物，三氟甲磺酸盐和氯化物与三苯基膦的磷酸化反应，生成芳基二苯基膦。NaI的添加提高了Pd / C磷化的速率和产率。
• Method for the Manufacture of Substituted Phosphanes, and Substituted Phosphanes Manufactured According to Said Method
  申请人：Thiel Werner

  公开号：US20080221335A1

  公开（公告）日：2008-09-11

  The invention relates to a method for the manufacture of substituted phosphanes and substituted phosphanes manufactured according to the method. Phosphanes, phosphane oxides, sulfides or selenides are used as ligands in coordination compounds. They play a central role in controlling the activity and selectivity of catalysts. The object is achieved by the invention by synthesizing heterocyclic substituents on aromatic groups by introducing acetyl groups. In this manner, previously unknown representatives of the families of phosphanes, phosphane oxides, sulfides and selenides are made accessible.

  本发明涉及一种制造取代膦和按照该方法制造的取代膦的方法。在配位化合物中，膦、膦氧化物、硫化物或硒化物被用作配体。它们在控制催化剂的活性和选择性方面起着核心作用。本发明通过在芳香族基团上引入乙酰基合成杂环取代基，从而实现了该目标。通过这种方法，膦、膦氧化物、硫化物和硒化物的新的未知代表得以获得。
• Method for the manufacture of substituted phosphanes, and substituted phosphanes manufactured according to said method
  申请人：Zylum Beteiligungsgesellschaft mbH & Co. Patent II KG

  公开号：US07910744B2

  公开（公告）日：2011-03-22

  The invention relates to a method for the manufacture of substituted phosphanes and substituted phosphanes manufactured according to the method. Phosphanes, phosphane oxides, sulfides or selenides are used as ligands in coordination compounds. They play a central role in controlling the activity and selectivity of catalysts. The object is achieved by the invention by synthesizing heterocyclic substituents on aromatic groups by introducing acetyl groups. In this manner, previously unknown representatives of the families of phosphanes, phosphane oxides, sulfides and selenides are made accessible.

  本发明涉及一种制备取代膦和按照该方法制备的取代膦的方法。膦、膦氧化物、硫化物或硒化物被用作配位化合物中的配体。它们在控制催化剂的活性和选择性方面起着核心作用。本发明通过在芳香族基团上引入乙酰基合成杂环取代基，从而实现了该目标。以这种方式，先前未知的膦、膦氧化物、硫化物和硒化物家族的代表变得可获得。
• Catalyst‐Free Visible Light Mediated Synthesis of Unsymmetrical Tertiary Arylphosphines
  作者：Dmitry I. Bugaenko、Alexander V. Karchava

  DOI：10.1002/adsc.202200309

  日期：2022.7.5

  Arylation of tertiary aryl and alkyl phosphines bearing 2-cyanoethyl group with aryl(mesityl)iodonium triflates under blue light irradiation followed by retro-Michael reaction of the in situ generated quaternary phosphonium salts initiated by DBU represent a novel efficient and general method for the preparation of distinctly substituted tertiary arylphosphines. An operationally simple, one-pot protocol

  在蓝光照射下，带有 2-氰乙基的叔芳基和烷基膦与芳基（异三苯甲基）碘鎓在蓝光照射下芳基化，然后由 DBU 引发的原位生成的季鏻盐的逆迈克尔反应代表了一种新的有效和通用的制备方法明显取代的叔芳基膦。操作简单的一锅法具有温和、不含过渡金属的条件、高选择性、广泛的官能团兼容性以及可扩展性，可应用于具有不同电子和空间性质的基材。