4-((diphenylphosphoryl)ethynyl)benzonitrile | 58971-88-3

• 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-((diphenylphosphoryl)ethynyl)benzonitrile
• 英文别名: 4-(2-Diphenylphosphorylethynyl)benzonitrile；4-(2-diphenylphosphorylethynyl)benzonitrile
• CAS: 58971-88-3
• 化学式: C₂₁H₁₄NOP
• 分子量: 327.322
• InChiKey: JJASEHNMBQBENC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-((diphenylphosphoryl)ethynyl)benzonitrile 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 34.0h， 生成 4-[2-[3-(2-Anthracen-9-ylethynyl)phenyl]ethynyl]benzonitrile
  参考文献：
  名称：

  One-Pot Transformation of Ph₂P(O)-Protected Ethynes: Deprotection Followed by Transition Metal-Catalyzed Coupling

  摘要：

  Ph2P(O)-protected ethynes were successfully transformed to arylethynes in one-pot manner through t-BuOK-catalyzed deprotection followed by Sonogashira coupling with aryl halide. The arylethynes were obtained similarly by Ph2P(O)-deprotection, stannylation of the resulting terminal ethynes, and Migita-Kosugi-Stille coupling. Deprotection followed by intramolecular Eglinton coupling could be carried out in one-pot to provide cyclic butadiynes.

  DOI：

  10.1021/jo402176w
• 作为产物：
  描述：

  diphenylphosphorylazide 在 三氟化硼乙醚 、 三乙胺 、 乙腈 作用下， 以 乙二醇二甲醚 、 乙醚 、 氯仿 为溶剂， 生成 4-((diphenylphosphoryl)ethynyl)benzonitrile
  参考文献：
  名称：

  Disteldorf,W.; Regitz,M., Chemische Berichte, 1976, vol. 109, p. 546 - 561

  摘要：

  DOI：

文献信息

• Photoredox-catalyzed decarboxylative alkylation/cyclization of alkynylphosphine oxides: a metal- and oxidant-free method for accessing benzo[<i>b</i>]phosphole oxides
  作者：Lixin Liu、Jianyu Dong、Yani Yan、Shuang-Feng Yin、Li-Biao Han、Yongbo Zhou

  DOI：10.1039/c8cc08689c

  日期：——

  By photoredox-catalysis, alkylation/aryl cyclization of alkynylphosphine oxides towards benzo[b]phospholes has been realized under metal- and oxidant-free conditions at room temperature.

  通过光氧化催化，在室温无金属和氧化剂条件下，实现了炔膦氧化物向苯并[b]膦的烷基化/芳基环化。
• Cs₂CO₃-Promoted One-Pot Synthesis of Alkynylphosphonates, -phosphinates, and -phosphine Oxides
  作者：Yulei Wang、Jiepeng Gan、Liu Leo Liu、Hang Yuan、Yuxing Gao、Yan Liu、Yufen Zhao

  DOI：10.1021/jo500312n

  日期：2014.4.18

  trialkyl phosphites, ethyl diphenylphosphinite, or diethyl phenylphosphonite has been developed under metal-free conditions, providing a practical and powerful tool for one-pot synthesis of valuable alkynylphosphonates, -phosphinates, and -phosphine oxides in good to excellent yields.

  在无金属条件下开发了一种新颖且有效的Cs 2 CO 3促进的各种1,1,1-二溴-1-烯烃与容易获得的亚磷酸三烷基酯，乙基二苯基亚膦酸酯或二乙基苯基亚膦酸酯的磷酸化或亚膦酰基化，提供了实用而有效的方法一锅合成有价值的炔基膦酸酯，-次膦酸酯和-膦氧化物的工具，产率很高。
• Copper-Catalyzed Direct Oxidative C–H Functionalization of Unactivated Cycloalkanes into Cycloalkyl Benzo[<i>b</i>]phosphole Oxides
  作者：Dumei Ma、Jiaoting Pan、Lu Yin、Pengxiang Xu、Yuxing Gao、Yingwu Yin、Yufen Zhao

  DOI：10.1021/acs.orglett.8b01108

  日期：2018.6.15

  The first simple and efficient Cu-catalyzed radical addition/cyclization of various unactivated cycloalkanes with diaryl(arylethynyl)-phosphine oxides has been developed, providing a general, one-step approach to construct a new class of important benzo[b]phosphole oxides via sequential C–H functionalization along with two new C–C bond formations.

  第一个简单并用二芳基（芳基乙炔） -膦氧化物各种未活化的环烷烃的高效铜催化的自由基加/环化已被开发出来，提供一种一般的，一步式的方法来构造一个新的类重要的苯并[ b ]磷杂环氧化物通过连续的C–H功能化以及两个新的C–C键形成。
• Visible-Light-Induced Oxidative C–H Functionalization of Unreactive Cycloalkanes, Alcohols, and Ethers with Alkynylphosphine Oxides into Benzo[<i>b</i>]phosphole Oxides under Photocatalyst-, Metal-, and Base-Free Conditions
  作者：Baffa Haruna、Weitu Hong、Warsame Ibrahim Mohamed、Jiami Guo、Liyi Ye、Yingwu Yin、Yuxing Gao、Song Tu

  DOI：10.1021/acs.joc.1c00841

  日期：2021.9.17

  We developed the radical cyclization/addition of alkynylphosphine oxides with easily available cycloalkanes, alcohols, and ethers using a visible-light and environmentally friendly synthetic strategy in the absence of photocatalyst at room temperature. This mild and metal- and base-free reaction provided a structurally varied set of significant benzo[b]phosphole oxides through sequential C–H functionalization

  我们在室温下，在没有光催化剂的情况下，使用可见光和环境友好的合成策略，开发了炔基氧化膦与容易获得的环烷烃、醇和醚的自由基环化/加成。这种温和且无金属和碱的反应通过以原子经济的方式连续 C-H 官能化提供了一组结构变化的重要苯并[ b ]磷氧化物。
• Silver-Free Direct Synthesis of Alkynylphosphine Oxides via <i>sp</i>C–H/P(O)–H Dehydrogenative Coupling Catalyzed by Palladium
  作者：Jian-Qiu Zhang、Tieqiao Chen、Ji-Shu Zhang、Li-Biao Han

  DOI：10.1021/acs.orglett.7b02389

  日期：2017.9.1

  silver-free palladium-catalyzed dehydrogenative phosphorylation of terminal alkynes with hydrogen phosphine oxides has been developed. Both aromatic and aliphatic terminal alkynes including those bearing functional groups coupled readily with hydrogen phosphine oxides, producing the corresponding value-added alkynylphosphine oxides in good to excellent yields. This reaction could be easily conducted

  已经开发了用氢膦氧化物的末端炔烃的无银钯催化的脱氢磷酸化。包括带有官能团的那些的芳族和脂族末端炔烃都容易与氢氧化膦偶联，从而以良好或优异的产率产生相应的增值的炔基氧化膦。该反应可以容易地以克级（10mmol）进行，而反应效率没有任何降低，在有机合成中显示出很高的潜在合成价值。提出了合理的Pd（0）/ Pd（II）机制。