4-(2-Diphenylphosphanylethynyl)benzonitrile | 764663-44-7

• 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-(2-Diphenylphosphanylethynyl)benzonitrile
• CAS: 764663-44-7
• 化学式: C₂₁H₁₄NP
• 分子量: 311.323
• InChiKey: HDUMQGNSOGVZCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 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：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(2-Diphenylphosphanylethynyl)benzonitrile 在 potassium tert-butylate 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 19.0h， 生成 4-[2-[3-(2-Diphenylphosphorylethynyl)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：

  乙炔基(二苯基)膦 在 正丁基锂 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 caesium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 3.5h， 生成 4-(2-Diphenylphosphanylethynyl)benzonitrile
  参考文献：
  名称：

  膦取代的炔基硼酸酯和炔基三氟硼酸酯盐的合成，表征和反应。

  摘要：

  报道了膦取代的炔基硼酸酯的合成和结构表征。由X射线晶体学研究2和相关的P（3）判断，以AP（III）为中心的炔基硼酸酯（2）几乎没有证据表明P-孤对通过炔π系统与硼结合。 V）化合物3。另外，制备相应的炔基三氟硼酸盐，与它们的硼酸酯对应物相比，它们显示出改善的稳定性。这些盐与芳基卤化物进行Pd催化的交叉偶联反应。

  DOI：

  10.3390/molecules191221324

文献信息

• Azobisisobutyronitrile-Initiated Oxidative C–H Functionalization of Simple Alcohols with Diaryl(arylethynyl)phosphine Oxides: A Metal-Free Approach toward Hydroxymethyl Benzo[<i>b</i>]phosphole Oxides and 6<i>H</i>-Indeno[2,1-<i>b</i>]phosphindole 5-Oxide Derivatives
  作者：Jiami Guo、Chenlu Mao、Bin Deng、Liyi Ye、Yingwu Yin、Yuxing Gao、Song Tu

  DOI：10.1021/acs.joc.0c00118

  日期：2020.5.15

  described with azobisisobutyronitrile as a radical initiator, affording an efficient and one-pot procedure to access a new class of hydroxymethyl benzo[b]phosphole oxides and 6H-indeno[2,1-b]phosphindole 5-oxides for potential application in organic materials via sequential C(sp3)-H/C(sp2)-H functionalization. The method employs easily accessible starting materials and is endowed with high regioselectivity

  用偶氮二异丁腈作为自由基引发剂，已经描述了用二芳基（芳基乙炔基）膦氧化物对简单的醇进行的首次无金属且容易的自由基加成/环化反应，并提供了一种有效的单罐方法来获得一类新的羟甲基苯并[b]。磷氧化物和6H-茚并[2,1-b]磷吲哚5-氧化物可通过连续的C（sp3）-H / C（sp2）-H官能化潜在地应用于有机材料。该方法采用易于获得的原料，并具有较高的区域选择性和宽泛的官能团耐受性。
• Ph2P(O) Group for Protection of Terminal Acetylenes
  作者：Akihiro Orita、Junzo Otera、Xin Yang、Daisuke Matsuo、Yoshinori Suzuma、Jing-Kun Fang、Feng Xu、Shingo Kajiyama、Nagatoshi Koumura、Kohjiro Hara

  DOI：10.1055/s-0030-1261223

  日期：2011.10

  A protecting group Ph2P(O) for terminal ethyne was newly developed. This protecting group can be introduced readily to terminal ethyne by CuI-catalyzed phosphination and subsequent oxidation with H2O2. Ph2P(O)-protected ethynes remained intact in Sonogashira coupling, and their high polarity enabled easy separation of the desired coupling product from by-products. By treatment with t-BuOK, Ph2P(O)-protected

  新开发了末端乙炔保护基Ph 2 P（O）。该保护基可以通过CuI催化的磷酸化并随后用H 2 O 2氧化而容易地引入末端乙炔。在Sonogashira偶联中，Ph 2 P（O）保护的乙炔保持完好无损，并且它们的高极性使得可以轻松将所需的偶联产物与副产物分离。通过用t -BuOK处理，Ph 2 P（O）保护的乙炔转化为相应的末端乙炔。 炔烃-磷酸化-保护基-偶联
• (<i>p</i>-cymene)Ruthenium(II)(diphenylphosphino)alkyne Complexes:  Preparation of (μ-Cl)(μ-PPh₂C⋮CR)-Bridged Ru/Pt Heterobimetallic Complexes
  作者：Jesús R. Berenguer、María Bernechea、Juan Forniés、Ana García、Elena Lalinde

  DOI：10.1021/om049676j

  日期：2004.8.1

  The neutral complexes [(eta(6)-p-cymene)RuCl2(PPh2C=CR)] (R = Ph 1, Bu-t 2, (4-CH3)C6H4 3, (4-C=CPh)C6H4 4, (4-CN)C6H4 5) have been synthesized by reacting [(p-cymene)RuCl2](2) with the respective alkynylphosphine. Treatment of 1-5 with AgOTf or TIPF6 and the corresponding PPh2C=CR allows the preparation of cationic bis(diphenylphosphino) compounds [(eta(6)-p-cymene)RuCl(PPh2C=CR)(2)]X (X = OTf; R = Ph 6, Bu-t 7, (4-CH3)C6H4 8, (4-C=CPh)C6H4 9, X = PF6; R = (4-CN)C6H4 10). All complexes have been characterized by analytical and spectroscopic methods, by cyclic voltammetry, and in several cases (3 and 7) by X-ray crystallography. Reactions of both neutral (1-4) and cationic (6-8) complexes with [cis-Pt(C6F5)(2)(thf)(2)] (thf = tetrahydrofuran) gave heterobimetallic neutral [(n(6)-p-cymene)Cl-Ru(mu-Cl)(mu-1kappaP:eta(2)-PPh2C=CR)Pt(C6F5)(2)] (R = Ph 11a, Bu-t 12a, (4-CH3)C6H4 13a, (4-C=CPh)-C6H4 14a and cationic [(eta(6)-p-cymene)(PPh2C=CR)Ru(rho-Cl)(mu-1kappaP:eta(2)-PPh2C=CR)Pt(C6F5)(2)]-(OTf) (R = Ph 15, Bu-t 16, (4-CH3)C6H4 17) derivatives stabilized by a mixed Cl/PPh2C=CR bridging system. The molecular structures of 12a and 17 have been confirmed by X-ray diffraction. However, the neutral complexes 11-14 existed in solution as a mixture of isomers [(eta(6)-p-cymene)ClRu(mu-Cl)(mu-Cl)(mu-1kappaP:eta(2)-PPh2C=CR)Pt(C6F5)(2)] (a) and [(eta(6)-p-cymene)(PPh2C=CR)Ru(mu-Cl)(2)Pt(C6F5)(2)] (b), respectively.