(4-ethynylphenyl)diphenylphosphine | 359017-78-0

• 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: (4-ethynylphenyl)diphenylphosphine
• 英文别名: (4-Ethynylphenyl)diphenylphosphane；(4-ethynylphenyl)-diphenylphosphane
• CAS: 359017-78-0
• 化学式: C₂₀H₁₅P
• 分子量: 286.313
• InChiKey: BNWJETJKJICTRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (4-ethynylphenyl)diphenylphosphine 在 potassium selenocyanate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以90%的产率得到
  参考文献：
  名称：

  Selenophosphine Derivatives with Pendant Electron-Rich Fe(κ²-dppe)(η⁵-C₅Me₅)C≡C– Substituents

  摘要：

  Five new selenophosphines (5a-d and 7) bearing organometallic Fe(kappa(2)-dppe)(eta(5)-C5Me5)C equivalent to C- substituents were synthesized and structurally characterized in order to determine the steric and electronic parameters of the parent metallo-phosphines (1a-d and 2). Their cone angles were estimated from available structural data, and their electronic parameters were derived from the (1)J(PSe) coupling constants. DFT calculations suggest that (1)J(PSe) constants can be used to determine their electronic parameters in spite of the existence of the low-lying excited states for 5a-d. Strong solvent effects were evidenced on (1)J(PSe), stressing the need to use a single solvent (CDCl3) for measuring these coupling constants if comparison of the electronic parameter of these with existing data is sought. Among the parent metallo-phosphines, 2 appears to be the most electron donating ligand by far. According to its (1)J(PSe) value, it resembles a tris(alkyl)phosphine but presents a significantly larger Tolman cone angle (theta(T) approximate to 172 degrees) than PPh3 (theta(T) approximate to 145 degrees).

  DOI：

  10.1021/om500211e
• 作为产物：
  描述：

  (4-溴苯基乙炔基)三甲基硅烷 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (4-ethynylphenyl)diphenylphosphine
  参考文献：
  名称：

  具有双核（4-乙炔基苯基）二苯基膦配体组装的具有高核银簇构建基的二维和三维乙炔化银骨架

  摘要：

  摘要合成了双功能配体前体（4-乙炔基苯基）二苯基膦，并用于构建乙炔银骨架。在三乙胺存在下，它与Ag（I）的反应提供了乙炔化银[AgL] n，其中L = Ph2P-C6H4-4-CC-可以充当双官能配体，同时具有与Ag（I）的苯基乙炔和膦结合位点。[AgL] n和AgCF3CO2在不同条件下的反应产生了四种乙炔化银。它们是[Ag18L8（CF3COO）6（HCO3）4（DMF）4] n（1，DMF =二甲基甲酰胺），[Ag20L8（CF3COO）12（DMF）6] n（2），[Ag17L6（CF3COO）9（HCO3 ）2] n（3）和[Ag17L6（CF3COO）9.58（HCO3）1.42] n（4）。晶体学研究表明，配合物1在三斜空间群P 1中结晶，其a = 14.1252（9）A，b = 18.6012（12）A，c = 25.2137（17）A，α= 108.340（2）°，β= 95

  DOI：

  10.1016/j.ica.2017.01.030

文献信息

• Mixed Heterotri‐ to Heteropentametallic Transition‐Metal Complexes: Synthesis, Characterization and Electrochemical Behavior
  作者：Rico Packheiser、Petra Ecorchard、Tobias Rüffer、Bernhard Walfort、Heinrich Lang

  DOI：10.1002/ejic.200800457

  日期：2008.9

  transition-metal complexes are discussed. Complex [(η 2 -dppf)(η 5 -C5H5)Ru-C=C-C6H4-4-PPh 2 ] (3) [dppf = 1,1'-bis(diphenylphosphanyl)ferrocene], accessible by treating [(η 2 -dppf)(η 5 -C 5 H 5 )RuCl] (1) with equimolar amounts of HC≡C-C 6 H 4 -4-PPh 2 (2), gives on treatment with [(cod)RhCl] 2 (4), [(η 5 -C 5 Me 5 )RhCl 2 ] 2 (6), and [(tht)AuCl] (8) heterotrimetallic [(η 2 -dppf)(η 5 -C5H5)Ru-C≡C-C6H4-4-PPh

  讨论了异质多金属过渡金属配合物的合成和反应化学。复合物 [(η 2 -dppf)(η 5 -C5H5)Ru-C=C-C6H4-4-PPh 2 ] (3) [dppf = 1,1'-双(二苯基膦基)二茂铁]，可通过处理 [( η 2 -dppf)(η 5 -C 5 H 5 )RuCl] (1) 与等摩尔量的 HC≡CC 6 H 4 -4-PPh 2 (2)，用 [(cod)RhCl] 2 ( 4)、[(η 5 -C 5 Me 5 )RhCl 2 ] 2 (6)和[(tht)AuCl] (8)异三金属[(η 2 -dppf)(η 5 -C5H5)Ru-C≡C -C6H4-4-PPh 2 -Rh}] [5, Rh} = (cod)RhCl; 7, Rh} = (η 5 -C 5 Me 5 )RhCl 2 ) 和[(η 2 -dppf)(η 5 -C 5 H 5 )Ru-C≡CC 6 H 4
• Tagged phosphine reagents to assist reaction work-up by phase-switched scavenging using a modular flow reactor
  作者：Christopher D. Smith、Ian R. Baxendale、Geoffrey K. Tranmer、Marcus Baumann、Stephen C. Smith、Russell A. Lewthwaite、Steven V. Ley

  DOI：10.1039/b703033a

  日期：——

  The use of three orthogonally tagged phosphine reagents to assist chemical work-up via phase-switch scavenging in conjunction with a modular flow reactor is described. These techniques (acidic, basic and Click chemistry) are used to prepare various amides and tri-substituted guanidines from in situ generated iminophosphoranes.

  本文描述了使用三种正交标记的膦试剂，通过相转移捕获辅助化学后处理，并结合模块化流动反应器。这些技术（酸性、碱性和点击化学）用于从原位生成的亚磷胺制备各种酰胺和三取代氨基腺嘌呤。
• Electrocatalytic Reduction of CO₂ into Formate with Glassy Carbon Modified by [Fe₄N(CO)₁₁(PPh₂Ph-linker)]⁻
  作者：David B. Cluff、Amela Arnold、James C. Fettinger、Louise A. Berben

  DOI：10.1021/acs.organomet.8b00396

  日期：2019.3.25

  electrodes covalently modified with [Fe4N(CO)12]− are active for electrocatalytic formate production from CO2 at −1.2 V vs SCE in aqueous solutions buffered at pH 5–9. The modified electrodes are stable for at least 4 days, as demonstrated using cyclic voltammetry experiments. Electrode modification was performed via cycloaddition of alkyne-functionalized [Fe4N(CO)12]− with azide-modified glassy-carbon

  如果将分子电催化剂结合到功能性光电化学装置中，则必须使其具有催化活性的固定化。大多数情况下，固定化会降低催化性能。用[Fe 4 N（CO）12 ] -共价修饰的玻璃碳电极可在-1.2 V vs SCE的pH 5–9缓冲水溶液中从CO 2电催化生成甲酸。如循环伏安法实验所示，修饰的电极至少可稳定4天。电极修饰是通过将叠氮基修饰的[Fe 4 N（CO）12 ] -与叠氮化物修饰的玻璃碳电极进行环加成而进行的。
• Two- and three-dimensional silver acetylide frameworks with high-nuclearity silver cluster building blocks assembled using a bifunctional (4-ethynylphenyl)diphenyl phosphine ligand
  作者：Shaokang Zhang、Zongyao Zhang、Rui Cao

  DOI：10.1016/j.ica.2017.01.030

  日期：2017.5

  V = 8660.2(6) A3, and Z = 2. The presence of Ag(I)–ethynide, Ag(I)–P and Ag(I)–Ag(I) bonding interactions makes all four silver acetylides to have two- and three-dimensional framework structures with unusual high-nuclearity silver cluster building blocks.

  摘要合成了双功能配体前体（4-乙炔基苯基）二苯基膦，并用于构建乙炔银骨架。在三乙胺存在下，它与Ag（I）的反应提供了乙炔化银[AgL] n，其中L = Ph2P-C6H4-4-CC-可以充当双官能配体，同时具有与Ag（I）的苯基乙炔和膦结合位点。[AgL] n和AgCF3CO2在不同条件下的反应产生了四种乙炔化银。它们是[Ag18L8（CF3COO）6（HCO3）4（DMF）4] n（1，DMF =二甲基甲酰胺），[Ag20L8（CF3COO）12（DMF）6] n（2），[Ag17L6（CF3COO）9（HCO3 ）2] n（3）和[Ag17L6（CF3COO）9.58（HCO3）1.42] n（4）。晶体学研究表明，配合物1在三斜空间群P 1中结晶，其a = 14.1252（9）A，b = 18.6012（12）A，c = 25.2137（17）A，α= 108.340（2）°，β= 95
• Stille-type aryl–aryl cross-coupling catalysis using triarylphosphine ligands with electron-rich Fe(ii)-alkynyl substituents
  作者：Guillaume Grelaud、Ayham Tohmé、Gilles Argouarch、Thierry Roisnel、Frédéric Paul

  DOI：10.1039/c1nj20480g

  日期：——

  The synthesis of four new phosphane ligands featuring electron-rich Fe(II) “(η2-dppe)(η5-C5Me5)FeCC-” substituents in para and meta position(s) on the aryl rings (1–4) is reported along with those of the corresponding PdCl2(PAr3)2 precatalysts (7–10). These precatalysts have then been tested in a Stille-type aryl–aryl cross coupling reaction. It is shown that these new ligands survive the reaction conditions and perform at least as well as the classic triphenylphosphine ligand for this transformation.

  报道了四种新磷配体的合成，这些配体具有富电子的Fe(II) “(η2-dppe)(η5-C5Me5)FeCC-”取代基，分别位于芳环的对位和间位（1-4），以及相应的PdCl2(PAr3)2前催化剂（7-10）。这些前催化剂随后在Stille型芳基-芳基交叉偶联反应中进行了测试。结果表明，这些新配体能够耐受反应条件，并且在该转化反应中至少表现得与经典的三苯基磷配体一样好。