(Z,Z)-1,4-bis(2-bromoethenyl)benzene | 88248-70-8

• 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: (Z,Z)-1,4-bis(2-bromoethenyl)benzene
• 英文别名: 1,4-bis[(Z)-2-bromoethenyl]benzene
• CAS: 88248-70-8
• 化学式: C₁₀H₈Br₂
• 分子量: 287.982
• InChiKey: ICURYTKGPGAYEO-SFECMWDFSA-N

物化性质

• 沸点：
  344.1±30.0 °C(Predicted)
• 密度：
  1.748±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• 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

• 作为反应物：
  描述：

  (Z,Z)-1,4-bis(2-bromoethenyl)benzene 在 platinum(IV) oxide copper(l) iodide 、 四(三苯基膦)钯 、 氢气 、 potassium carbonate 、 正丁胺 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 21.0 ℃ 、101.33 kPa 条件下， 反应 36.0h， 生成 三环[16.2.2.28,11]二十四碳-8,10,18,20(1),21,23-六烯
  参考文献：
  名称：

  Revolveneynes: Novel eneyneparacyclophanes by sequential palladium coupling

  摘要：

  The synthesis and initial study of a new series of eneyne-bridged cyclophanes (revolveneynes) are described in which the phenyl rings are free to rotate within the cavity. Either palladium coupling or oxidative dimerization provided rapid access to [14], [6.6] and [8.8] phane systems.

  DOI：

  10.1016/s0040-4039(00)76948-6
• 作为产物：
  描述：

  1,4-phenylenediacrylic acid 在 溴 、 三乙胺 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 (Z,Z)-1,4-bis(2-bromoethenyl)benzene
  参考文献：
  名称：

  Matveeva; Erin; Kurz, Russian Journal of Organic Chemistry, 1997, vol. 33, # 8, p. 1065 - 1067

  摘要：

  DOI：

文献信息

• Stereoselective Synthesis of <i>cis</i>- and <i>trans</i>-Oligo(phenylenevinylene)s via Palladium-Catalyzed Cross-Coupling Reactions
  作者：Hiroyuki Katayama、Masato Nagao、Fumiyuki Ozawa、Masashi Ikegami、Tatsuo Arai

  DOI：10.1021/jo052602c

  日期：2006.3.31

  cis-Oligo(phenylenevinylene)s (OPVs) are synthesized by Suzuki−Miyaura coupling of arylboronic acids with (Z)-bromoalkenes in over 96% geometrical purity. On the other hand, trans-oligo(phenylenevinylene)s can be synthesized by Hiyama coupling of aryl iodide with (E)-alkenylsilanes in almost perfect purities. Effect of π-conjugation chain length on photoisomerization behavior of OPVs is described.

  顺式-低聚（亚苯基亚乙烯基）（OPV）是通过芳族硼酸与（Z）-溴代烯烃的Suzuki-Miyaura偶联以96％以上的几何纯度合成的。另一方面，反式-低聚（亚苯基亚乙烯基）可以通过芳基碘化物与（E）-烯基硅烷的Hiyama偶联以几乎完美的纯度来合成。描述了π共轭链长度对OPVs光异构化行为的影响。
• Use of Precipitons for Copper Removal in Atom Transfer Radical Polymerization
  作者：Mical E. Honigfort、William J. Brittain、Todd Bosanac、Craig S. Wilcox

  DOI：10.1021/ma020155m

  日期：2002.6.1
• Highly (<i>Z</i>)-Selective Hydrosilylation of Terminal Alkynes Catalyzed by a Diphosphinidenecyclobutene-Coordinated Ruthenium Complex:  Application to the Synthesis of (<i>Z</i>,<i>Z</i>)-Bis(2-bromoethenyl)arenes
  作者：Masato Nagao、Kimihiro Asano、Kazutoshi Umeda、Hiroyuki Katayama、Fumiyuki Ozawa

  DOI：10.1021/jo051908g

  日期：2005.12.1

  Complex 1 bearing a diphosphinidenecyclobutene ligand (DPCB-OMe) catalyzes highly stereoselective hydrosilylation of diethynylarenes with HSiMe2Ph to afford (Z,Z)-bis(2-silylethenyl)arenes. Treatment of the hydrosilylation products with N-bromosuccinimide causes bromodesilylation in a stereospecific manner, giving (Z,Z)-bis(2-bromoethenyl)arenes in high geometrical purity (> 98%).
• Stereocontrolled Synthesis and Optical Properties of All-cis Poly(phenylene vinylenes) (PPVs):  A Method for Direct Patterning of PPVs
  作者：Hiroyuki Katayama、Masato Nagao、Tatsuro Nishimura、Yukio Matsui、Kazutoshi Umeda、Kensuke Akamatsu、Takaaki Tsuruoka、Hidemi Nawafune、Fumiyuki Ozawa

  DOI：10.1021/ja042853n

  日期：2005.3.1

  Geometrically pure, all-cis poly(phenylene vinylenes) (PPVs) are synthesized by Suzuki-Miyaura-type polycondensation of 2,5-dioctyloxy-1,4-benzenediboronic acid with (Z, Z)-bis(2-bromoethenyl)benzenes, which are prepared by ruthenium-catalyzed (Z)-selective double hydrosilylation of diethynylbenzenes, followed by bromodesilylation of the resulting (Z, Z)-bis(2-silylethenyl)benzenes with N-bromosuccinimide. The all-cis PPVs thus obtained undergo one-way photoisomerization to the corresponding trans-PPVs both in solution and in the solid. This phenomenon is applied to direct microscale patterning of PPVs onto a quartz substrate.
• Romero Miguel A., Fallis Alex G., Tetrahedron Lett, 35 (1994) N 27, S 4711-4714
  作者：Romero Miguel A., Fallis Alex G.

  DOI：——

  日期：——