diphenyl(2-(pyridin-4-yl)ethyl)phosphine oxide | 134778-88-4

• 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: diphenyl(2-(pyridin-4-yl)ethyl)phosphine oxide
• 英文别名: 4-[2-(Diphenylphosphoryl)ethyl]pyridine；4-(2-diphenylphosphorylethyl)pyridine
• CAS: 134778-88-4
• 化学式: C₁₉H₁₈NOP
• mdl: MFCD00401617
• 分子量: 307.332
• InChiKey: FVJPVEVIFZICTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(2-(diphenylphosphino)ethyl)pyridine 在 双氧水 作用下， 以 乙醚 、 水 为溶剂， 反应 0.17h， 以37.8 mg的产率得到diphenyl(2-(pyridin-4-yl)ethyl)phosphine oxide
  参考文献：
  名称：

  钴（I）钳配合物对活化的烯烃进行氢磷酸化

  摘要：

  在本文中，我们报告了三种含咔唑NNN钳形配体的第一排过渡金属（II）杂合剂的合成，并通过还原羰基化途径转化为相应的金属（I）-羰基配合物。这些络合物是活化烯烃进行加氢磷酸化的预催化剂，提供了钴催化的加氢磷酸化过程，该过程仅可选择性地产生β加成（抗马尔科夫尼科夫）产物。已经使用多种活化的烯烃研究了这种转化的范围。底物配位中间体的分离和表征揭示了可用的配位点，可提供对拟议催化循环的深入了解。

  DOI：

  10.1002/adsc.202000514

文献信息

• Lanthanum-Catalyzed Regioselective Anti-Markovnikov Hydrophosphinylation of Styrenes
  作者：Yesmin Akter Rina、Joseph A. R. Schmidt

  DOI：10.1021/acs.organomet.9b00549

  日期：2019.11.11

  A useful and convenient method for sp3 C–P(O) bond formation via direct regioselective hydrophosphinylation of simple and readily available alkenes using a lanthanum-based N,N-dimethylbenzylamine complex (La(DMBA)3) as a precatalyst is demonstrated. The reaction proceeds with perfect atom economy for a wide range of styrenes with secondary phosphine oxides, giving moderate to excellent yields.

  通过使用基于镧的N，N-二甲基苄胺络合物（La（DMBA）3）作为预催化剂，对简单易用的烯烃进行直接区域选择性氢膦化作用，从而形成了sp 3 C-P（O）键的有用且便捷的方法。对于具有仲氧化膦的各种苯乙烯，反应以完美的原子经济性进行，得到中等至极好的收率。
• Hydrophosphinylation of Styrenes Catalysed by Well‐Defined s‐Block Bimetallics
  作者：Andrew W. J. Platten、Andryj M. Borys、Eva Hevia

  DOI：10.1002/cctc.202101853

  日期：2022.3.8

  s-Block heterobimetallic catalysts: Exploiting s-block cooperativity, the use of a heterobimetallic potassium magnesiate for the catalytic hydrophosphinylation of styrenes has been developed.

  s-嵌段杂双金属催化剂：利用 s-嵌段协同性，已开发出使用杂双金属镁酸钾来催化苯乙烯的氢膦酰化。
• Magnesium-Catalyzed Regioselective Hydrophosphinylation of Alkenes with Diarylphosphine Oxides
  作者：Lei Zhang、Shaokun Bai、Lijiao Zheng

  DOI：10.1021/acs.organomet.3c00247

  日期：2023.8.28

  regioselective hydrophosphinylation of alkenes with secondary phosphine oxides (SPOs) via anti-Markovnikov addition to access structurally diverse organophosphorus compounds is described. This transformation features perfect atom economy, good functional group tolerance, and divergent regioselectivity toward vinylarenes and α,β-unsaturated carbonyl derivatives. Mechanistic studies revealed that the active

  描述了通过反马尔可夫尼科夫加成反应，在镁催化下，烯烃与二氧化膦 (SPO) 发生区域选择性氢膦酰化，从而获得结构多样的有机磷化合物。该转化具有完美的原子经济性、良好的官能团耐受性以及对乙烯基芳烃和α,β-不饱和羰基衍生物的不同区域选择性。机理研究表明，活性催化物质可能是原位生成的带有 Ph 2 PO -部分的 O 结合镁络合物。
• Blue‐Light Driven Iron‐Catalyzed Oxy‐phosphinylation of Activated Alkenes for β‐Ketophosphine Oxide Synthesis
  作者：Yumeng Yuan、Qiufeng Huang、Christophe Darcel

  DOI：10.1002/chem.202302358

  日期：2023.12.11

  driven iron-catalyzed oxy-phosphinylation of activated alkenes with secondary phosphine oxides under air at room temperature led to β-ketophosphine oxides in 43–97 % isolated yields. The proposed mechanism involved a blue light promoted aerobic process catalyzed by iron which generated a phosphorus radical from the starting secondary phosphine oxide.

  室温下，在空气中，蓝光驱动的铁催化的活化烯烃与二级氧化膦的氧膦酰化反应产生了 β-酮氧化膦，分离产率为 43-97%。所提出的机制涉及由铁催化的蓝光促进的有氧过程，铁从起始的二级氧化膦产生磷自由基。
• Protonation of phosphinylmethylpyridines and their N-oxides in nitromethane
  作者：E. I. Matrosov、A. G. Matveeva、G. V. Bodrin、B. K. Shcherbakov、Yu. M. Polikarpov、M. I. Kabachnik

  DOI：10.1007/bf00958580

  日期：1991.4

  The protonation of phosphinylmethylpyridines with different structures and their N-oxides differing both in the nature and the number of functional groups (pyridine nitrogen, N --> O, and P = O) was studied by potentiometric titration in nitromethane and IR spectroscopy. Regardless of the number of P = O groups, all the investigated phosphinylmethylpyridines were N bases, and their pK values changed in the range 10.4-4.7. In the case of N-oxides of phosphinylmethylpyridines, the oxygen atoms of N --> O and P = O groups participated simultaneously in protonation, and the pK values were 6.7-5.0. The structure of the protonation products is discussed.