bis[2-(2-pyridyl)ethyl]phosphine selenide | 1143571-21-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: bis[2-(2-pyridyl)ethyl]phosphine selenide
• 英文别名: Bis(2-pyridin-2-ylethyl)-selenidophosphanium；bis(2-pyridin-2-ylethyl)-selenidophosphanium
• CAS: 1143571-21-4
• 化学式: C₁₄H₁₇N₂PSe
• 分子量: 323.236
• InChiKey: DKCMQBSKSJXEPE-UHFFFAOYSA-N

物化性质

• 熔点：
  40-41 °C(Solvent: Hexane)
• 沸点：
  457.9±55.0 °C(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bis[2-(2-pyridyl)ethyl]phosphine selenide 在 氧气 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 0.17h， 生成 bis[2-(2-pyridyl)-ethyl]phosphine oxide
  参考文献：
  名称：

  Synthesis of chalcophosphinic acid amides with pyridine rings*

  摘要：

  DOI：

  10.1007/s10593-012-0925-2
• 作为产物：
  描述：

  bis[2-(pyridin-2-yl)ethyl]phosphine 在 selenium 作用下， 以 苯 为溶剂， 生成 bis[2-(2-pyridyl)ethyl]phosphine selenide
  参考文献：
  名称：

  仲膦硒化物向芳香族乙炔的立体选择性自由基加成

  摘要：

  在芳基乙炔中进行自由基选择性加成（AIBN，65–70°C，5–7 h）次膦基硒化物，使其立体选择性生成反马氏复合物（主要为Z构型）（高达97％），分离产率为60-80％ ，因此代表了向三键立体选择性自由基加成的罕见例子。微波辐射（600 W）和相同含量的AIBN会使反应时间减少到8分钟，尽管会影响立体选择性。在UV引发下，反应由于伯Z-加合物的异构化而失去其立体选择性。在该反应中，已经揭示了芳族取代基在三键处的特定的促进和控制Z构型的作用。

  DOI：

  10.1016/j.jorganchem.2008.11.043

文献信息

• Reaction of divinyl selenide with secondary phosphine chalcogenides
  作者：N. K. Gusarova、P. A. Volkov、N. I. Ivanova、N. A. Chernysheva、S. V. Yas’ko、A. I. Albanov、B. A. Trofimov

  DOI：10.1134/s1070363210080104

  日期：2010.8

  Under the conditions of free-radical initiation (AIBN, UV irradiation), divinyl selenide regioselectively reacts with secondary phosphine sulfides and phosphine selenides to afford, depending on the ratio of the reagents, mono- or diadducts mainly of the anti-Markownikoff structure. The conditions which allow obtaining the diadducts in up to 97% yield are found. By the example of 2-[2-(diphenethylphosphoroselenoyl) ethyl]selanyl}ethyl(diphenethyl)phosphine selenide the diadducts were shown to react with aqueous hydrogen peroxide at 53-56A degrees C to give vinyl(diphenethyl)phosphine oxide in 76% yield.
• Reaction of imidazole series aldeydes with bis[2-(2-pyridyl)ethyl]-phosphine chalcogenides: Synthesis of polyfunctional heterocyclic systems
  作者：N. I. Ivanova、P. A. Volkov、L. V. Baikalova、N. K. Gusarova、B. A. Trofimov

  DOI：10.1007/s10593-009-0196-8

  日期：2008.11

  The nucleophilic addition of bis[2-(2-pyridyl)ethyl]phosphine sulfide and bis[2-(2-pyridyl)-ethyl]phosphine selenide to 2-formyl-1-organylimidazoles and benzimidazoles occurs efficiently without catalysis at room temperature to give functionalized heterocyclic compounds containing imidazole, benzimidazole, and pyridine rings and also chalcogenophosphoryl and hydroxyl groups.
• Directed synthesis of tertiary phosphine chalcogenides with pyridine and hydroxy functions
  作者：N. I. Ivanova、P. A. Volkov、N. K. Gusarova、L. I. Larina、B. A. Trofimov

  DOI：10.1134/s1070363211020071

  日期：2011.2

  Secondary phosphine chalcogenides react with pyridine-2-, pyridine-3-, and pyridine-4-carbaldehydes under mild noncatalytic conditions (22-43A degrees C, 1-8.5 h) to form in 81-98% yield functional tertiary phosphine chalcogenides containing pyridine and hydroxy functions.
• Reaction of secondary phosphine chalcogenides with 2,2,2-trichloroacetaldehyde
  作者：N. I. Ivanova、N. K. Gusarova、N. A. Konovalova、P. A. Volkov、G. G. Levkovskaya、L. I. Larina、B. A. Trofimov

  DOI：10.1134/s1070363209100041

  日期：2009.10

  The nucleophilic addition of secondary phosphine chalcogenides to 2,2,2-trichloroacetaldehyde proceeds under mild noncatalytic conditions (12-25dgC, 15-90 min) with the formation of functional tertiary phosphine chalcogenides, containing hydroxy groups in up to 98% yield. Using the method of concurrent reactions the reactivity of secondary phosphine chalcogenides in this reaction was shown to decrease in the order: (PhCH2CH2)(2)P(O)H a parts per thousand << (PhCH2CH2)(2)P(S)H > (PhCH2CH2)(2)P(Se)H, and the secondary bis[2-(2-pyridyl) ethyl]-phosphine oxide was more reactive than bis(2-phenethyl)phosphine oxide.
• Stereoselective free-radical addition of secondary phosphine selenides to aromatic acetylenes
  作者：Boris A. Trofimov、Nina K. Gusarova、Svetlana N. Arbuzova、Nina I. Ivanova、Alexander V. Artem’ev、Pavel A. Volkov、Igor’ A. Ushakov、Svetlana F. Malysheva、Vladimir A. Kuimov

  DOI：10.1016/j.jorganchem.2008.11.043

  日期：2009.3

  Free-radical addition (AIBN, 65–70 °C, 5–7 h) of secondary phosphine selenides to arylacetylenes proceeds stereoselectively to give anti-Markovnikov adducts of predominantly Z-configuration (up to 97%) in 60–80% isolated yields, thus representing a rare example of stereoselective free-radical addition to the triple bond. Microwave irradiation (600 W) of the reactants with the same content of AIBN reduces

  在芳基乙炔中进行自由基选择性加成（AIBN，65–70°C，5–7 h）次膦基硒化物，使其立体选择性生成反马氏复合物（主要为Z构型）（高达97％），分离产率为60-80％ ，因此代表了向三键立体选择性自由基加成的罕见例子。微波辐射（600 W）和相同含量的AIBN会使反应时间减少到8分钟，尽管会影响立体选择性。在UV引发下，反应由于伯Z-加合物的异构化而失去其立体选择性。在该反应中，已经揭示了芳族取代基在三键处的特定的促进和控制Z构型的作用。