all-cis-1,3,5,7-octatetraene | 1871-50-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: all-cis-1,3,5,7-octatetraene
• 英文别名: di-cis-1,3,5,7-octatetraene；di-cis-octatetraene；octatetraene；cis,cis-1,3,5,7-octatetraene；octa-1,3c,5c,7-tetraene；cis,cis-1,3,5,7-Octatetraen；Octa-1,3c,5c,7-tetraen；cis,cis-Octatetraene；(3Z,5Z)-octa-1,3,5,7-tetraene
• CAS: 1871-50-7
• 化学式: C₈H₁₀
• 分子量: 106.167
• InChiKey: VXQUABLSXKFKLO-SFECMWDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• 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：

  (1Z,3Z,5Z)-Cycloocta-1,3,5-triene 以 正辛烷 为溶剂， 生成 all-cis-1,3,5,7-octatetraene
  参考文献：
  名称：

  顺式，顺式，1,3,5,7-辛酸酯的光化学制备与鉴定

  摘要：

  DOI：

  10.1021/j100222a017

文献信息

• Picosecond time-resolved UV resonance Raman spectroscopy of the photochemical ring opening of 1,3,5-cyclooctatriene and .alpha.-phellandrene
  作者：Philip J. Reid、Stephen J. Doig、Richard A. Mathies

  DOI：10.1021/j100385a006

  日期：1990.11
• Barriers in the excited 2 ¹<i>A</i>_<i>g</i> state for the <i>c</i><i>i</i><i>s</i>,<i>t</i><i>r</i><i>a</i><i>n</i><i>s</i> isomerization of <i>c</i><i>i</i><i>s</i>,<i>c</i><i>i</i><i>s</i>‐octatetraene: General features of the excited state potential
  作者：Bryan E. Kohler、Pradip Mitra、Paul West

  DOI：10.1063/1.451789

  日期：1986.10.15

  The lifetime of the excited 2 1Ag state of cis,cis-octatetraene (the eight carbon oligomer of cis-polyacetylene) in a n-octane host crystal has been measured as a function of temperature in the region 8&lt;T&lt;116 K. The lifetime is relatively long at 8 K (130 ns), drops to a lower value at approximately 30 K, and then begins to decrease rapidly with increasing temperature in the neighborhood of 100 K. The highly resolved optical spectra show unambiguously that at 30 K the decrease in lifetime is associated with thermal isomerization to cis,trans-octatetrane in the excited 2 1Ag state. These data are combined with other spectroscopic and kinetic data to obtain estimates for the energies of all three double bond isomers in ground and excited states and the activation energies for double bond isomerization in the excited state.
• Photochemical preparation and identification of cis,cis-1,3,5,7-octatetraene
  作者：Musharraf Hossain、Bryan E. Kohler、Paul West

  DOI：10.1021/j100222a017

  日期：1982.12
• Excited‐state structure and photochemical ring‐opening dynamics of 1,3,5‐cyclo‐octatriene from absolute resonance Raman intensities
  作者：Mary K. Lawless、Richard A. Mathies

  DOI：10.1063/1.466498

  日期：1994.2.15

  Absolute resonance Raman cross sections are measured for 1,3,5-cyclo-octatriene (COT) in cyclohexane with excitation from 325 to 200 nm. These intensities and the absorption spectrum are modeled using a fully thermalized time-correlator theory to quantitate the excited-state equilibrium geometry displacements along 19 Raman-active normal modes. The resonance Raman spectra show significant intensity in low-frequency modes corresponding to planarization of the eight-membered ring. The 140 cm−1 twist-boat planarization (Δ=4.6) and the 339 cm−1 ring deformation (Δ=1.6) are particularly strong. However, no intensity is observed in modes which project onto the predicted disrotatory ring-opening motion, such as the nontotally symmetric CH2 twist fundamental or its overtone. Analysis of the fluorescence quantum yield (φF=2×10−6) gives an excited state lifetime on the order of ∼30 fs. These results show that ring planarization is the first step in the disrotatory ring opening of COT followed by rapid depopulation of the initially prepared state to a lower-lying excited electronic state upon which the actual ring opening occurs. Comparison of these results with the excited-state dynamics of other pericyclic systems suggests that pericyclic rearrangements occur only once a planar structure is established and that the bond rearrangement occurs predominantly on a low-lying, optically forbidden excited state.