1,5-di(naphthalen-1-yl)penta-1,4-diyn-3-one | 915208-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,5-di(naphthalen-1-yl)penta-1,4-diyn-3-one
• CAS: 915208-13-8
• 化学式: C₂₅H₁₄O
• 分子量: 330.386
• InChiKey: SCRAFXVZCUVBLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  26.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1,5-di(naphthalen-1-yl)penta-1,4-diyn-3-one 在 1,1'-双(二苯基膦)二茂铁 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 氯苯 作用下， 反应 24.5h， 以78%的产率得到1,4-di(1-naphthyl)butadiyne
  参考文献：
  名称：

  Rh(I)-Catalyzed Decarbonylation of Diynones via C–C Activation: Orthogonal Synthesis of Conjugated Diynes

  摘要：

  Utilization of C-C bond activation as a unique mode of reactivity for constructing C-C bonds provides new strategies for preparing important organic molecules. Development of a Rh(I)-catalyzed C-C activation of diynones to synthesize symmetrical and unsymmetrical conjugated diynes through decarbonylation is reported. This C-C cleavage strategy takes advantage of the innate reactivity of conjugated ynones without relying on any ring strain or auxiliary directing group. This alkynation method also has orthogonal properties compared to typical cross-coupling reactions.

  DOI：

  10.1021/ol400815y
• 作为产物：
  描述：

  1,5-di(naphthalen-1-yl)penta-1,4-diyn-3-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以91%的产率得到1,5-di(naphthalen-1-yl)penta-1,4-diyn-3-one
  参考文献：
  名称：

  Rh(I)-Catalyzed Decarbonylation of Diynones via C–C Activation: Orthogonal Synthesis of Conjugated Diynes

  摘要：

  Utilization of C-C bond activation as a unique mode of reactivity for constructing C-C bonds provides new strategies for preparing important organic molecules. Development of a Rh(I)-catalyzed C-C activation of diynones to synthesize symmetrical and unsymmetrical conjugated diynes through decarbonylation is reported. This C-C cleavage strategy takes advantage of the innate reactivity of conjugated ynones without relying on any ring strain or auxiliary directing group. This alkynation method also has orthogonal properties compared to typical cross-coupling reactions.

  DOI：

  10.1021/ol400815y

文献信息

• Synthesis of 4-(Iso)Quinolinyl-3(<i>2H</i> )-furanones from (Iso)Quinoline <i>N</i> -oxides and 1,4-Diyn-3-ones: A Comparison of Copper Catalysis and Metal-free Reaction
  作者：Xuetong Li、Tao Wang、Zunting Zhang

  DOI：10.1002/adsc.201801382

  日期：2019.2.19

  A facile synthesis of (iso)quinolinyl‐3(2H)‐furanones from (iso)quinoline N‐oxides and 1,4‐diyn‐3‐ones in the presence of copper catalyst or under metal‐free conditions was developed. The resulting (iso)quinolinyl‐3(2H)‐furanones could be easily converted to (iso)quinolinyl‐isoxazoles, pyrazoles and polycyclic (iso)quinoline derivatives. In addition, the success in one‐pot, metal‐free synthesis of

  在铜催化剂存在下或在无金属条件下，由（异）喹啉N-氧化物和1,4-二炔基-3-酮可轻松合成（异）喹啉基-3（2H）-呋喃酮。生成的（iso）quinolinyl-3（2H）-呋喃酮很容易转化为（iso）quinolinyl-isoxazoles，吡唑和多环（iso）quinoline衍生物。此外，从异喹啉开始一锅法无金属合成异喹啉基-3（2H）-呋喃酮的成功表明，该方法具有对吡啶，喹啉和异喹啉进行无金属衍生化的能力。
• Phospholones from Diacetylenic Ketones: Synthesis, Properties, and Reactivity
  作者：Martin Obermeier、Anna I. Arkhypchuk

  DOI：10.1021/acs.joc.9b00076

  日期：2019.3.15

  The reactivity of phosphanyl phosphonates toward diacetylenic ketones was studied. Reactions resulted in the selective formation of phospholones via phosphaalkene intermediates. Phospholones were obtained in yields of 37–96% depending on the substituent on the acetylenic unit. Reduction of the phenyl-substituted phospholone resulted in the formation of a persubstituted phosphole bearing a hydroxyl

  研究了膦酰基膦酸酯对二炔酮的反应性。反应导致通过膦烯中间体选择性地形成膦酮。根据炔属单元上的取代基，获得的膦类化合物的收率为37–96％。苯基取代的膦酮的还原导致形成在3位带有羟基的全取代的磷脂，产率为64％，并且其氧化导致草酰膦酮的产率为77％。这两种修饰均导致化合物的光电性能发生实质性变化，并导致最长波长吸收最大值的红移。