(3-ethynylphenyl)diphenylphosphine | 1240453-64-8

• 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: (3-ethynylphenyl)diphenylphosphine
• 英文别名: [m-(HCC)C6H4]PPh2；(3-Ethynylphenyl)-diphenylphosphane；(3-ethynylphenyl)-diphenylphosphane
• CAS: 1240453-64-8
• 化学式: C₂₀H₁₅P
• 分子量: 286.313
• InChiKey: FKYNQGDLRBFQFO-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：

  (3-ethynylphenyl)diphenylphosphine 在 potassium selenocyanate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以78%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：

  [m-(HOMe2CCC)C6H4]PPh2 在 potassium hydroxide 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以90%的产率得到(3-ethynylphenyl)diphenylphosphine
  参考文献：
  名称：

  Synthesis of new triphenylphosphines with pending ethynyl substituents

  摘要：

  The straightforward isolation and characterization of new triphenylphosphines possessing a pendent ethynyl substituent on one or several peripheral aryl ring(s) are reported. The synthesis of this family of compounds is achieved by retro-Favorsky reactions from the corresponding propargylic alcohol derivatives, themselves obtained following a classic Sonogashira-type coupling between the ad hoc bromophenyl phosphines and 2-methylbut-3-yn-2-ol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.055

文献信息

• 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。
• Synthesis of Photochromic Phosphines by Pd‐Catalyzed Annulation Reaction of Alkynes Bearing Phosphinyl Substituent with a Silacyclopropene
  作者：Akshitha Selvaraj、Marie Cordier、Marc Devillard、Gilles Alcaraz

  DOI：10.1002/chem.202302374

  日期：2023.11.24

  A methodological approach for the preparation of unconventional DTE-based photochromic phosphines is reported. It relies on the Pd-catalyzed annulation reaction of alkynyl phosphines in the presence of a silirene.

  报道了一种制备基于 DTE 的非常规光致变色膦的方法。它依赖于在硅烯存在下，钯催化的炔基膦成环反应。
• Triarylphosphine Ligands with Pendant Electron-Rich “[Fe(κ²-dppe)(η⁵-C₅Me₅)(C≡C)]–” Substituents
  作者：Ayham Tohmé、Guillaume Grelaud、Gilles Argouarch、Thierry Roisnel、Arnaud Bondon、Frédéric Paul

  DOI：10.1021/ic4011828

  日期：2013.8.5

  The synthesis of four triaylphosphine ligands featuring electron-rich Fe(II) "Fe(kappa(2)-dppe)(eta(5)-C5Me5)C C-" pendant substituents in para and meta position(s) (1-4) is reported along with that of their corresponding radical cations (1- 2[PF6] or 3-4[PF6](3)). These triarylphosphines possessing redox-active organometallic substituents constitute a new class of phosphorus-based metallo-ligands. In contrast to many related ferrocenylphosphines, these metallo-ligands are stable and isolable in two redox-states. Their steric and electronic properties are also briefly discussed.
• Selenophosphine Derivatives with Pendant Electron-Rich Fe(κ²-dppe)(η⁵-C₅Me₅)C≡C– Substituents
  作者：Ayham Tohmé、Hiba Sahnoune、Thierry Roisnel、Vincent Dorcet、Jean-François Halet、Frédéric Paul

  DOI：10.1021/om500211e

  日期：2014.7.14

  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).
• Synthesis of new triphenylphosphines with pending ethynyl substituents
  作者：Guillaume Grelaud、Gilles Argouarch、Frédéric Paul

  DOI：10.1016/j.tetlet.2010.05.055

  日期：2010.7

  The straightforward isolation and characterization of new triphenylphosphines possessing a pendent ethynyl substituent on one or several peripheral aryl ring(s) are reported. The synthesis of this family of compounds is achieved by retro-Favorsky reactions from the corresponding propargylic alcohol derivatives, themselves obtained following a classic Sonogashira-type coupling between the ad hoc bromophenyl phosphines and 2-methylbut-3-yn-2-ol. (C) 2010 Elsevier Ltd. All rights reserved.