(E)-1-(p-iodophenyl)-2-(4-pyridyl)ethene | 543745-21-7

• 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: (E)-1-(p-iodophenyl)-2-(4-pyridyl)ethene
• 英文别名: 4-[2-(4-iodophenyl)vinyl]pyridine；(E)-4-(4-iodostyryl)pyridine；4-[(E)-2-(4-iodophenyl)ethenyl]pyridine
• CAS: 543745-21-7
• 化学式: C₁₃H₁₀IN
• 分子量: 307.134
• InChiKey: SXZOGBKFPVLDIZ-OWOJBTEDSA-N

物化性质

• 熔点：
  194-197 °C
• 沸点：
  380.6±21.0 °C(Predicted)
• 密度：
  1.634±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-(p-iodophenyl)-2-(4-pyridyl)ethene 以 氯仿 为溶剂， 生成 4-[(Z)-2-(4-iodophenyl)ethenyl]pyridine
  参考文献：
  名称：

  体积要求顺式4 -stilbazole的几何异构化。结晶态的HCl盐：探索亚稳二聚体的作用

  摘要：

  顺式-反式异构化是溶液中烯烃的最常见且经过充分研究的光反应之一。这是通过C C键上的取代基之一旋转180°来实现的，需要在双键周围留出较大的空间。人们会期望在晶体中相邻的分子会阻止这种过程。尽管如此，Schmidt及其同事在1960年代初报告说，这种过程是通过2 + 2'间位环丁烷'的形成在晶体中发生的。在这项研究中，通过检查四种顺式-噻唑鎓盐的光化学，我们表明通过2 + 2加成不会发生光转化为相应的反式异构体。大的分离度可确保相邻烯烃之间有足够的空间，有利于顺式-晶体中的反式异构化。令人费解的一个方面是产物反式异构体相在母体顺式晶体内分离并重结晶，并光二聚为环丁烷二聚体。该现象的细节将被理解。

  DOI：

  10.1016/j.jphotochem.2015.07.017
• 作为产物：
  描述：

  (4-iodobenzyl)triphenylphosphonium bromide 在 potassium tert-butylate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 60.5h， 生成 (E)-1-(p-iodophenyl)-2-(4-pyridyl)ethene
  参考文献：
  名称：

  π-Extended conjugate phenylacetylenes. Synthesis of 4-[(E) and (Z)-2-(4-ethenylphenyl)ethenyl]pyridine. Dimerization, quaternation and formation of charge–transfer complexes

  摘要：

  The conjugate (E)- and (Z)-(4'-pyridylethenyl)-4-phenylethyne (E-4 and Z-4) has been satisfactorily prepared by two different routes: (a) by dehydrohalogenation of 4'-pyridylethenyl-4-phenyi-beta-chloroethene; (b) by the Wittig reaction between p-(iodobenzyl)(triphenyl)phosphine ylide and 4-pyridinecarboxaldehyde, E/Z isomer separation, and cross-coupling with 2-methyl-but-3-yn-2-ol followed the propanone elimination. The Glaser oxidative dimerization of (Z)-4 yields (Z,Z)-1,4-di[(4'-pyridylethenyl)-4-phenyll-buta-1,3-diyne in good yield, (Z,Z)-5. (E,E)-5 was obtained by phase transfer oxidative dimerisation of (E)-4 in presence of their N-methyl salt (E)-10. Mono-and di-N-methylated salts of conjugate (E,E)-5 and (Z,Z)-5, were obtained by quaternation with iodomethane. The (Z,Z)-5 di-N-methylated salt forms charge-transfer complexes with TCNE, TCNQ and TMPD. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01628-9

文献信息

• Role of hydrogen bonds in molecular packing of photoreactive crystals: templating photodimerization of protonated stilbazoles in crystalline state with a combination of water molecules and chloride ions
  作者：Barnali Mondal、Tingting Zhang、Rajeev Prabhakar、Burjor Captain、V. Ramamurthy

  DOI：10.1039/c4pp00221k

  日期：2014.11

  photobehavior and molecular packing between hydrated and anhydrous crystals of protonated trans-stilbazoles has been identified. While stilbazoles are not photoreactive in the crystalline state, upon protonation with HCl in the solid state they dimerized to a single dimer (anti-head-tail) when exposed to UV light. In these photoreactive crystals the protonated stilbazole molecules are arranged in a ladder-like

  已鉴定出质子化反式-噻唑的水合晶体和无水晶体在光行为和分子堆积方面的差异。尽管噻唑在晶体状态下不具有光反应性，但在固态HCl质子化后，当暴露于UV光时它们会二聚为一个二聚体（反头尾）。在这些光反应性晶体中，质子化的斯蒂巴唑分子以梯状排列，梯级由水分子和氯离子组成。水和氯离子的组合通过N-HO或N-HCl（-）相互作用保留质子化反式-噻唑。通过在减压下加热“湿”晶体而制备的无水质子化的斯蒂巴唑晶体在暴露于紫外光时是惰性的。根据X射线晶体结构分析，这些光稳定晶体的晶格中不包含水分子。目前的研究已经确定，水分子对于结晶质子化反式噻唑类化合物的二聚化至关重要。为了比较质子化反式-stilbazoles和质子化顺式-stilbazoles的反应性，研究了顺式-4-碘stilbazole.HCl盐的光反应性和堆积排列。该处于结晶状态的分子仅异构化为反式异构体，并且不二聚。因此，尽管反式异构体二聚并且不
• Mechanistic Aspects of Aryl–Halide Oxidative Addition, Coordination Chemistry, and Ring‐Walking by Palladium
  作者：Olena V. Zenkina、Ori Gidron、Linda J. W. Shimon、Mark A. Iron、Milko E. van der Boom

  DOI：10.1002/chem.201501580

  日期：2015.11.2

  that the reaction with palladium may proceed through a dissociation–oxidative addition mechanism rather than through a haptotropic intramolecular process (i.e., ring walking). Furthermore, the transition state involves coordination of a third phosphine to the palladium center, which is lost during the oxidative addition as the Chalide bond is being broken. Interestingly, selective activation of aryl

  这一贡献描述了零价钯膦配合物与同时包含芳基卤化物部分和不饱和碳-碳键的底物的反应性。虽然η 2与金属中心到CC或CC单元的-coordination是动力学有利的，芳基卤键活化在热力学上是有利的。这些定量转化在溶液或固态的温和反应条件下进行。动力学测量表明，形成η的2配位配合物不是非生产性的侧平衡，而是在芳基卤化物键断裂的过程中可观察到的（甚至在某些情况下甚至是分离的）中间体。同时，DFT计算表明与钯的反应可能是通过离解-氧化加成机理进行的，而不是通过触变分子内过程（即环行）进行的。此外，过渡态还涉及第三膦与钯中心的配位，这在氧化加成过程中会由于C 1-4卤化物键断裂而失去。有趣的是，芳基卤化物的选择性激活已经证明通过添加反应性的芳基卤化物的η 2协调中心。产物分布可通过反应物的浓度和/或过量膦的存在来控制。
• Electroactive compounds, compositions and devices and methods of making the same
  申请人：ATOCHEM NORTH AMERICA, INC.

  公开号：EP0491364A2

  公开（公告）日：1992-06-24

  The present invention relates to electroactive compounds capable of undergoing a change in light absorption and refraction due to an applied electric field and a permanent change in refraction due to exposure to predetermined bands of optical radiation. The present invention also relates to electroactive compositions containing such electroactive compounds, electrooptical components comprised of such electroactive compositions and electrooptical devices

  本发明涉及能够因外加电场而改变光吸收和折射以及因暴露于预定波段的光辐射而永久改变折射的电活性化合物。本发明还涉及含有这种电活性化合物的电活性组合物、由这种电活性组合物组成的光电元件和光电设备。
• Directing Aryl−I versus Aryl−Br Bond Activation by Nickel via a Ring Walking Process
  作者：Olena V. Zenkina、Amir Karton、Dalia Freeman、Linda J. W. Shimon、Jan M. L. Martin、Milko E. van der Boom

  DOI：10.1021/ic702289n

  日期：2008.6.1

  Activation of a strong aryl-Br bond of a halogenated vinylarene by nickel(0) is demonstrated in the presence of aryl-I containing substrates. eta(2)-Coordination of Ni(PEt3)(2) to the C=C moiety of halogenated vinylarenes is kinetically preferable and is followed by an intramolecular aryl-halide bond activation process. This "ring-walking" process is quantitative and proceeds under mild reaction conditions in solution. Mechanistic studies indicate that the metal insertion into the aryl-halide bond is not the rate-determining step. The reaction obeys first-order kinetics in the eta(2)-Coordination complexes with almost identical activation parameters for Br and I derivatives. The ring-walking process is kinetically accessible as shown by density functional theory (DFT) calculations at the PBE0/SDB-ccpVDZ//PBE0/SDD level of theory.
• US5334333A
  申请人：——

  公开号：US5334333A

  公开（公告）日：1994-08-02