(E)-dimethyl-diphenylbutatriene | 133296-86-3

• 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)-dimethyl-diphenylbutatriene
• 英文别名: 1,4-Dimethyl-1,4-diphenyl-butatrien
• CAS: 133296-86-3
• 化学式: C₁₈H₁₆
• 分子量: 232.325
• InChiKey: MTCZLSMIVWEJJF-NXVVXOECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (E)-dimethyl-diphenylbutatriene 反应 4.0h， 生成 (E)-dimethyl-diphenylbutatriene
  参考文献：
  名称：

  SYNTHESIS OF SUBSTITUTED BUTATRIENES AND NOVEL STRUCTURES OF THEIR O₂-OXIDATION PRODUCTS

  摘要：

  介绍了三种 2,3-二碘-1,3-二烯的合成以及将这些二烯转化为丁三烯的过程。2,5-二甲基六-2,3,4-三烯在暴露于空气中时发生聚合，生成聚合过氧化物 (C6H12O2)n，该过氧化物被重新分配为包含乙炔和过氧化物单元的结构。

  DOI：

  10.1246/cl.1984.131
• 作为产物：
  描述：

  2,5-二苯基己-3-炔-2,5-二醇 在 正丁基锂 、 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (E)-dimethyl-diphenylbutatriene
  参考文献：
  名称：

  SYNTHESIS OF SUBSTITUTED BUTATRIENES AND NOVEL STRUCTURES OF THEIR O₂-OXIDATION PRODUCTS

  摘要：

  介绍了三种 2,3-二碘-1,3-二烯的合成以及将这些二烯转化为丁三烯的过程。2,5-二甲基六-2,3,4-三烯在暴露于空气中时发生聚合，生成聚合过氧化物 (C6H12O2)n，该过氧化物被重新分配为包含乙炔和过氧化物单元的结构。

  DOI：

  10.1246/cl.1984.131

文献信息

• A NEW AND CONVENIENT SYNTHESIS OF ARYL-SUBSTITUTED BUTATRIENES USING NICKEL-CATALYZED COUPLING OF ARYL-SUBSTITUTED 1,1-DIBROMOETHENES
  作者：Masahiko Iyoda、Masahiro Sakaitani、Tatsuya Miyazaki、Masaji Oda

  DOI：10.1246/cl.1984.2005

  日期：1984.11.5

  The reactions of aryl-substituted 1,1-dibromoethenes with in situ generated tetrakis(triphenylphosphine)nickel(0) in the presence of tetraethylammonium iodide give aryl-substituted butatrienes.

  在四乙基碘化铵的存在下，芳基取代的 1,1-二溴乙烯与原位生成的四（三苯基膦）镍 (0) 的反应得到芳基取代的丁三烯。
• A new approach to the construction of radialenes by the nickel-catalyzed cyclooligomerization of [3]cumulenes (butatrienes)
  作者：Masahiko. Iyoda、Shigeyoshi. Tanaka、Hiroyuki. Otani、Masanori. Nose、Masaji. Oda

  DOI：10.1021/ja00233a028

  日期：1988.12
• Temperature dependence of aryl butatriene fluorescence: barrier to twisting on S1 for 1,1,4,4-tetraphenylbutatriene
  作者：Robert E. Connors、Veeradej Chynwat、Christine H. Clifton、Tracy L. Coffin

  DOI：10.1016/s0022-2860(97)00363-3

  日期：1998.2

  The temperature dependence of aryl butatriene fluorescence is assigned to a competition between radiative decay and butatriene chain rotation against a barrier followed by radiationless decay from S-1. Fluorescence quantum yields were measured as a function of temperature for 1,1,4,4-tetraphenylbutatriene (TPBT) in a series of n-alkane solvents. Application of the medium-enhanced barrier model and transition state theory allow the observed barrier to be expressed in terms of an intrinsic and solvent-induced contribution (Delta H-obsd(double dagger) = H-t(double dagger) + Delta H-v(double dagger)) It is found that there is little or no intrinsic barrier to rotation(Delta H-t(double dagger) = 0.075 +/- 0.155 kcal/mol) on S-1 for TPBT. The solvent-induced component is related to E-eta, the activation energy for viscous flow, by Delta H-v(double dagger) = aE(eta) with a = 0.86 +/- 0.06 for TPBT. This is in contrast to twisting on S-1 for trans-stilbene for which a significant intrinsic barrier has been reported. AM1 molecular orbital calculations for gas phase TPBT show a twist angle of similar to 0 degrees on S-0 with a barrier to rotation of 20.1 kcal/mol. Consistent with the experimental results, the calculations show that TPBT undergoes a barrierless relaxation on S-1 from its Franck-Condon structure to a minimum with a twist angle of 85.6 degrees. (C) 1998 Elsevier Science B.V.