diphenylcyanophosphine | 4791-48-4

• 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: diphenylcyanophosphine
• 英文别名: diphenylphosphinous cyanide；cyanodiphenylphosphane；cyanodiphenylphosphine；Diphenyl-cyanphosphan；Diphenyl-cyan-phosphin；Cyanodiphenylphosphin；diphenylphosphanylformonitrile
• CAS: 4791-48-4
• 化学式: C₁₃H₁₀NP
• 分子量: 211.203
• InChiKey: CSTJIJYJEWKYGH-UHFFFAOYSA-N

物化性质

• 沸点：
  180-182 °C(Press: 1.5 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  diphenylcyanophosphine 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以73%的产率得到二苯基膦
  参考文献：
  名称：

  Synthesis of hydridophosphines by the reduction of P(III) isothiocyanates and cyanides

  摘要：

  DOI：

  10.1007/bf00958063
• 作为产物：
  描述：

  氢氰酸 、 二苯基氯化膦 在 三乙胺 作用下， 以 苯 为溶剂， 生成 diphenylcyanophosphine
  参考文献：
  名称：

  Synthesis of Dialkyl Phosphorocyanidites. Axial Preference of theP-Cyano Group in the 1,3,2-Dioxaphosphorinane Ring System

  摘要：

  DOI：

  10.1055/s-1975-23915
• 作为试剂：
  描述：

  (4-碘丁氧基)苯 在 六甲基二锡 、 diphenylcyanophosphine 作用下， 以 苯 为溶剂， 反应 12.0h， 以17%的产率得到丁氧基苯
  参考文献：
  名称：

  Radical Cyanation of Alkyl Iodides with Diethylphosphoryl Cyanide

  摘要：

  首次观察到来自亚胺基自由基的含磷有机物β-消除反应。基于这一发现，通过使用二乙基磷酰基氰化物，实现了烷基碘的自由基氰化反应。

  DOI：

  10.1055/s-0028-1087385

文献信息

• Preparation and multinuclear NMR and IR spectroscopic characterization of some complexes of acetyldiphenylphosphine, diphenyl(2-thienyl)phosphine, bis(2-thienyl)phenylphosphine and cyanodiphenylphosphine
  作者：Ashima Varshney、Gary M. Gray

  DOI：10.1016/s0020-1693(00)87504-0

  日期：1988.8

  The syntheses and multinuclear NMR and IR spectroscopic characterizations of some mononuclear Mo, Pd and Pt complexes of acetyldiphenylphosphine, diphenyl(2-thienyl)phosphine, bis(2-thienyl)phenylphosphine and cyanodiphenylphosphine are presented. The NMR and IR spectra of the Mo carbonyl complexes indicate that the electron-donor ability of the P substituents increases in the order CN < C(O)Me < 2-thienyl

  介绍了乙酰二苯基膦，二苯基（2-噻吩基）膦，双（2-噻吩基）苯基膦和氰基二苯基膦的一些单核Mo，Pd和Pt配合物的合成以及多核NMR和IR光谱表征。Mo羰基配合物的NMR和IR光谱表明，P取代基的电子给体能力按CN
• Cyanide initiated perfluoroorganylations with perfluoroorgano silicon compounds
  作者：Patricia Panne、Dieter Naumann、Berthold Hoge

  DOI：10.1016/s0022-1139(01)00513-9

  日期：2001.12

  Cyanophenylphosphanes, Ph2PCN or PhP(CN)2, do not react with Me3SiCF3 or Me3SiC6F5 in the absence of cyanide ions. Catalytic amounts of ionic cyanides such as [NEt4]CN, [18-crown-6-K]CN or NaCN initiate perfluoroorganylation reactions. The trifluoromethylphosphines, Ph2PCF3 and PhP(CF3)2, as well as the pentafluorophenylphosphines, Ph2PC6F5 and PhP(C6F5)2, are isolated in 60–75% yield. In dimethylformamide

  在没有氰化物离子的情况下，氰基苯基膦Ph 2 PCN或PhP（CN）2不会与Me 3 SiCF 3或Me 3 SiC 6 F 5反应。催化量的离子型氰化物，例如[NEt 4 ] CN，[18-冠-6-K] CN或NaCN引发全氟有机化反应。三氟甲基膦Ph 2 PCF 3和PhP（CF 3）2以及五氟苯基膦Ph 2 PC 6 F 5和PhP（C 6 F 5）2被分离，产率为60-75％。在二甲基甲酰胺或丙酮溶液中，观察到副反应，而在CH 2 Cl 2和乙腈中的反应则选择性进行。我3 SICF 3除了二甲基甲酰胺和丙酮的羰基发生在治疗的Me 3 SICF 3种这些溶剂与催化量的氰化物，氰酸盐或即使在低温下硫氰酸盐的溶液。通过低温NMR研究证明在与过量的[18-冠-6-K] CN反应中反应性硅酸盐[Me 3 Si（CN）CF 3 ] -的形成。
• Schmidpeter, Alfred; Zirzow, Karl-Heinz; Burget, Guenther, Chemische Berichte, 1984, vol. 117, # 5, p. 1695 - 1706
  作者：Schmidpeter, Alfred、Zirzow, Karl-Heinz、Burget, Guenther、Huttner, Gottfried、Jibril, Ibrahim

  DOI：——

  日期：——
• Synthetic equivalents of 2-lithiophosphinines: new routes to 2-functional phosphinines
  作者：Pascal Le Floch、Duncan Carmichael、Francois Mathey

  DOI：10.1021/om00053a055

  日期：1991.7

  Two routes converting 2-bromophosphinines into 2-functional phosphinines are described. In the first one, a [2 + 4] cycloadduct between the 2-bromophosphinine, 2,3-dimethylbutadiene, and sulfur is first formed. On this adduct, a bromine to lithium exchange is performed by phenyllithium in THF at low temperature. This lithium derivative is converted into a functional derivative by reaction with an electrophile. Then, the 2-functional phosphinine is obtained by a combined reduction-cycloreversion using P(CH2CH2CN)3 as the reducing agent at ca. 180-degrees-C. A 2-(trimethylsilyl)- and a 2-(diphenylphosphino)phosphinine were thus prepared. In the second route, a bromine to lithium exchange is performed on a (2-bromophosphinine)pentacarbonyltungsten complex by phenyllithium in THF at -80-degrees-C. The 2-functional phosphinine is recovered from its complex by heating with Ph2PCH2CH2PPh2 at 110-degrees-C in toluene. A 2-iodo-, 2-(trimethylsilyl)-, and 2-[(diphenylphosphino)pentacarbonyltungsten]phosphinine were thus obtained. An intermediate [2-(ethoxycarbonyl)phosphinine]pentacarbonyltungsten complex readily adds water to give the corresponding 1-hydroxy-1,6-dihydrophosphinine complex.
• Pudovik, A. N.; Nazmutdinova, V. N., Journal of general chemistry of the USSR, 1988, vol. 58, # 10, p. 1973 - 1976
  作者：Pudovik, A. N.、Nazmutdinova, V. N.

  DOI：——

  日期：——