1,1'-[2-(phenylethynyl)-1-buten-3-yne-1,4-diyl]bisbenzene | 610283-14-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 1,1'-[2-(phenylethynyl)-1-buten-3-yne-1,4-diyl]bisbenzene
• 英文别名: (4-phenyl-2-phenylethylnylbut-1-en-3-ynyl)benzene；(2-(phenylethynyl)but-1-en-3-yne-1,4-diyl)dibenzene；1,5-Diphenyl-3-benzylidene-1,4-pentadiyne；(3-benzylidene-5-phenylpenta-1,4-diynyl)benzene
• CAS: 610283-14-2
• 化学式: C₂₄H₁₆
• 分子量: 304.391
• InChiKey: YDEILDLWMPRAOR-UHFFFAOYSA-N

物化性质

• 沸点：
  469.1±45.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  苯乙炔 在 正丁基锂 、 二氯二茂锆 、 四氯苯醌 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 21.0h， 以67%的产率得到1,1'-[2-(phenylethynyl)-1-buten-3-yne-1,4-diyl]bisbenzene
  参考文献：
  名称：

  在对氯苯醌存在下锆茂促进的末端乙炔与双烯二炔的偶联反应

  摘要：

  在醌存在下炔基锂与二氧化锆茂反应，以高收率得到锆二烯二炔。在CuCl存在下用对氯苯腈处理锆烯二炔以良好的产率得到1,1,4,4-四乙炔基-1,3-二烯。在CuCl和/或Pd（PPh 3）4的存在下，锆烯二炔可以通过与亲电试剂的偶联反应转化为各种烯二炔衍生物。

  DOI：

  10.1016/j.jorganchem.2007.04.028

文献信息

• Highly Selective Synthesis of (<i>E</i>)-3-Methyl-1-trialkylsilyl-3-en-1-ynes via <i>trans</i>-Selective Alkynylation Catalyzed by Cl₂Pd(DPEphos) and Stereospecific Methylation with Methylzincs Catalyzed by Pd(<i>^t</i>Bu₃P)₂
  作者：Ji-cheng Shi、Xingzhong Zeng、Ei-ichi Negishi

  DOI：10.1021/ol030017x

  日期：2003.5.1

  [reaction: see text] trans-Selective (>or=98%) monoalkynylation of 1,1-dibromo-1-alkenes and 1,1-dichloro-1-alkenes catalyzed by Cl(2)Pd(DPEphos) followed by stereospecific methylation with Me(2)Zn or MeZnX (X= Cl or Br) catalyzed by Pd((t)()Bu(3)P)(2) provides an efficient and stereoselective (>or=98%) route to 5, convertible to a wide variety of enynes and conjugated dienes. In the cases of 1,1-dibromo-1-alkenes

  [反应：见正文]由Cl（2）Pd（DPEphos）催化的立体选择性催化的1,1-二溴-1-烯烃和1,1-二氯-1-烯烃的反式选择性（>或= 98％）单烷基化由Pd（（t）（）Bu（3）P）（2）催化的Me（2）Zn或MeZnX（X = Cl或Br）甲基化可提供有效且立体选择性的途径（>或= 98％）生成5，可转换为多种烯炔和共轭二烯。在1，1-二溴-1-链烯的情况下，Sonogashira炔基化也可能是令人满意的，但是在使用1，1-二氯-1-链烯的情况下，它明显不如炔基锌反应令人满意。
• Synthesis of conjugated enediynes via palladium catalyzed cross-coupling reactions of potassium alkynyltrifluoroborates
  作者：George W. Kabalka、Gang Dong、Bollu Venkataiah

  DOI：10.1016/j.tetlet.2004.12.021

  日期：2005.1

  An efficient synthesis of cross-conjugated enediynes has been developed utilizing the palladium catalyzed cross-coupling reactions of 1,1-dibromo-1-alkenes with potassium alkynyltrifluoroborates under mild conditions.

  利用钯在温和条件下催化1,1-二溴-1-烯烃与炔基三氟硼酸钾的交叉偶联反应，开发了一种有效的交叉共轭二炔合成方法。
• Photophysics and peripheral ring size dependent aggregate emission of cross-conjugated enediynes: applications to white light emission and vapor sensing
  作者：Anuja Singh、Avik Kumar Pati、Ashok Kumar Mishra

  DOI：10.1039/c7cp08091c

  日期：——

  local nature of the dominant electronic transition. The optimized ground state geometries of the dyes from partially to fully propeller shaped structures confirm the ring-size dependence of the aggregates. The LE and aggregate state emissions are judiciously exploited to generate single-component white light emission in binary solvent mixtures. The excited state photophysics are further applied toward

  用π-共轭支架对有机荧光团进行光物理理解是至关重要的，因为此类染料对于光电应用至关重要。这项工作提出了详细的光物理研究一类的交叉共轭的同和杂烯二炔（Y形）外围连接到常见的芳香族部分，如苯，萘和蒽。位于Y形双烯炔三极的三个芳族单元之间的交叉通信电子通信产生宽S 0 →S 1吸收带和局部激发（LE）发射信号。除LE发射带外，在非水溶剂中观察到某些染料的红移聚集发射，其中聚集的荧光的出现表明外围芳香环的大小明显相关。从基态吸收光谱变化和时间分辨的荧光衰减研究中没有上升时间可以明显看出，这些聚集体本质上是静态的，通过核磁共振光谱法和单晶X射线衍射实验进一步证实了这些聚集体。分子轨道计算支持主导电子跃迁的局部性质。从部分到完全螺旋桨状结构的染料的最佳基态几何形状证实了聚集体的环尺寸依赖性。明智地利用LE和聚集态发射在二元溶剂混合物中产生单组分白光发射。激发态光物理学进一步应用于固态的非质子极性蒸气感测。
• Synthesis and Photophysical Studies of Bis-enediynes as Tunable Fluorophores
  作者：Gil Tae Hwang、Hyung Su Son、Ja Kang Ku、Byeang Hyean Kim

  DOI：10.1021/ja0349148

  日期：2003.9.1

  We have synthesized a family of bis-enediynes by two complementary Pd/Cu-catalyzed Sonogashira cross-coupling methods. One is a modified Sonogashira reaction between the TMS-protected tetraalkyne 20 (or 21) and various aromatic bromides to afford bis-enediynes 22a-d and 23a-d bearing different peripheral aryl units. The other, the reaction of bifunctional 1,1-dibromo-1-alkenes with phenylacetylene, afforded a series of bis-enediynes 24-32 bearing various core aryl groups. These chemical modifications to the core and periphery of bis-enediynes induce dramatic changes in absorption and emission spectra. Bis-enediynes 22 and 23 show a large Stokes shift of about 50-110 nm when compared to the less-conjugated bis-enediynes 20 and 21. Absorptions and emissions of bis-enediynes 25, 27-29, and 31 were red-shifted relative to those of enediyne 35. Substantial increases in fluorescence quantum yields are observed as a result of extending the T-conjugation. The emission wavelength of bis-enediynes was tailored from indigo blue to reddish-orange, suggesting that the color of emission can be tunable by modification of the core and/or peripheral units.
• Palladium-catalyzed trans-selective alkynylation–alkylation tandem process for the synthesis of (E)-3-alkyl-1-trialkylsilyl-3-alken-1-ynes
  作者：Ei-ichi Negishi、Ji-cheng Shi、Xingzhong Zeng

  DOI：10.1016/j.tet.2005.07.100

  日期：2005.10

  The Pd-catalyzed trans-selective monoalkynylation of 1,1-dihalo-l-alkenes with XZnC CSiMe3, where X is Br or Cl, can proceed generally in excellent yields in the presence of Pd(DPEphos)Cl-2 or Pd(dppf)Cl-2, and subsequent alkylation with methyl- and ethylzincs can proceed in excellent yields with >= 98% retention of configuration in the presence of Pd((BU3P)-B-t)(2) as a catalyst. (c) 2005 Elsevier Ltd. All rights reserved.