(E,Z)-1,6-diphenylhexa-1,5-diene | 33788-20-4

• 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,Z)-1,6-diphenylhexa-1,5-diene
• 英文别名: (E,Z)-1,6-Diphenyl-1,5-hexadien；1c,6t-diphenyl-hexa-1,5-diene；1c,6t-Diphenyl-hexa-1,5-dien；(E,Z)-1,6-Diphenylhexa-1,5-dien；1.6-Diphenyl-1,5-hexadien；[(1Z,5E)-6-phenylhexa-1,5-dienyl]benzene
• CAS: 33788-20-4
• 化学式: C₁₈H₁₈
• 分子量: 234.341
• InChiKey: GXBNHFMSIXKWHZ-JTAXDKCCSA-N

物化性质

• 熔点：
  37 °C
• 沸点：
  395.8±42.0 °C(Predicted)
• 密度：
  1.008±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  meso-3,4-diphenylhexa-1,5-diene 以 正己烷 为溶剂， 127.5 ℃ 、100.0 kPa 条件下， 生成 (E,Z)-1,6-diphenylhexa-1,5-diene 、 (1E,5E)-1,6-diphenyl-1,5-hexadiene
  参考文献：
  名称：

  Diedrich, Matthias K.; Hochstrate, Dirk; Klaerner, Frank-Gerrit, Angewandte Chemie, 1994, vol. 106, # 10, p. 1135 - 1137

  摘要：

  DOI：

文献信息

• Perturbation of the Degenerate, Concerted Cope Rearrangement by Two Phenyl Groups in Active Positions of (E)-1,4-Diphenylhexa-1,5-diene. Acceleration by High Pressure as Criterion of Cyclic Transition States
  作者：W. von E. Doering、Ludmila Birladeanu、Keshab Sarma、Joaquim Henrique Teles、F.-G. Klaerner、Jan-Stephan Gehrke

  DOI：10.1021/ja00089a018

  日期：1994.5

  Previous examinations of radical-stabilizing substituents in the two distinct types of position in the hypothetical ''aromatic'' transition state of the thermal Cope rearrangement, designated ''a'' or active and ''n'' or nodal after the allyl radical, have concentrated on their effect in the ''n'' positions. In order to provide a quantitatively reliable reference for the ''a'' position, the activation parameters of the degenerate rearrangement of (6-C-13)-1,4-diphenylhexa-1,5-diene have been evaluated: E(a) = 30.8 +/- 0.4 kcal/mol; log A = 10.14 +/- 0.2. The soundly energetically-based proposition that these observations relate to a concerted mechanism is strongly supported by the observation of a 3.0-fold increase in rate of approach to equilibrium on increasing the pressure from 1 bar to 6000 bar (162 degrees C; benzene-d(6)). This rearrangement, like that of cis-1,2-divinylcyclobutane and rac- and meso-3,4-diphenylhexa-1,5-diene, has a negative volume of activation. In contrast, trans-1,2-divinylcyclobutane, which does not rearrange by a cyclic transition state and gives cycloocta-1,5-diene, 4-vinylcyclohexene and butadiene as products, has a positive volume of activation. To place the possibility of reaction by the homolytic/colligative (dissociative/recombinative) mechanism on a ''quantitative'' base, a further sighting on the heat of formation of the cinnamyl radical is provided by activation parameters for thermal syn-anti equilibration between (E)- and (Z)-1,1'-bi-3-phenylcyclohex-2-enylidene: E(a) = 35.8 +/- 0.2 kcal/mol; log A = 12.7 +/- 0.1. After correction for conjugative interaction between phenyl and the double bond in the educts and without regard for any proposed structure for the transition state, the two phenyl groups in ''a'' positions appear to have lowered the enthalpy of activation by 7.7 kcal/mol relative to the paradigm, hexa-1,5-diene, whereas the two phenyl groups in the ''n'' positions of 3,5-diphenylhexa-1,5-diene have lowered the enthalpy of activation by 17.0 kcal/mol.
• Mondon, Justus Liebigs Annalen der Chemie, 1957, vol. 603, p. 115,127
  作者：Mondon

  DOI：——

  日期：——
• Diedrich, Matthias K.; Hochstrate, Dirk; Klaerner, Frank-Gerrit, Angewandte Chemie, 1994, vol. 106, # 10, p. 1135 - 1137
  作者：Diedrich, Matthias K.、Hochstrate, Dirk、Klaerner, Frank-Gerrit、Zimny, Bernd

  DOI：——

  日期：——