4a,4b-dihydrophenanthrene

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 4a,4b-dihydrophenanthrene
• 英文别名: (4aS,4bS)-4a,4b-dihydrophenanthrene
• 化学式: C₁₄H₁₂
• 分子量: 180.249
• InChiKey: ZQNQJMXFVWUBDO-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  4a,4b-dihydrophenanthrene 在 碘 作用下， 生成 菲
  参考文献：
  名称：

  改进的芪光环化工艺合成菲和螺旋烯衍生物

  摘要：

  已经开发了一种改进的方法，用于二苯乙烯的光环化以构建菲和苯并 [c] 菲。该反应由碘促进，而四氢呋喃用作...

  DOI：

  10.1246/bcsj.82.1182
• 作为产物：
  描述：

  二苯乙烯 生成 4a,4b-dihydrophenanthrene
  参考文献：
  名称：

  改进的芪光环化工艺合成菲和螺旋烯衍生物

  摘要：

  已经开发了一种改进的方法，用于二苯乙烯的光环化以构建菲和苯并 [c] 菲。该反应由碘促进，而四氢呋喃用作...

  DOI：

  10.1246/bcsj.82.1182

文献信息

• Ultrafast Ring Closure Reaction of Gaseous <i>cis</i>-Stilbene from S₁(ππ*)
  作者：Shutaro Karashima、Xincheng Miao、Akio Kanayama、Yo-ichi Yamamoto、Junichi Nishitani、Nikita Kavka、Roland Mitric、Toshinori Suzuki

  DOI：10.1021/jacs.2c12266

  日期：2023.2.15

  4b-dihydrophenanthrene (DHP) in solution with a quantum yield of less than 0.19. The ring closure reaction, however, has never been identified for gaseous cis-St, and a recent computational simulation predicted the quantum yield of DHP to be only 0.04. In the present study, we identified an ultrafast ring closure reaction of gaseous cis-St for the first time using extreme ultraviolet time-resolved photoelectron

  顺式-二苯乙烯 ( cis -St) 是一种众所周知的顺反式光异构化基准系统。顺式-St 还在溶液中产生 4a,4b-二氢菲 (DHP)，量子产率小于 0.19。然而，气态顺式-St的闭环反应从未被发现，最近的计算模拟预测 DHP 的量子产率仅为 0.04。在本研究中，我们确定了气态顺式的超快闭环反应-St 首次使用极紫外时间分辨光电子能谱。SA3-XMS-CASPT2(2,2) 理论水平的表面跳跃轨迹计算再现了观察到的时间分辨光电子光谱的特征，并预测顺式-St :DHP:反式-St 分支比为 0.55:0.41： 0.04，与之前的估计相比。结果表明，在隔离条件下，光激发的顺式-St 比顺式-反式异构化更有利于环闭合。
• cis-Stilbene photochemistry: solvent dependence of the initial dynamics and quantum yields
  作者：Jon Marc Rodier、Anne B. Myers

  DOI：10.1021/ja00076a041

  日期：1993.11

  Photochemical quantum yields for the formation of trans-stilbene and 4a,4b-dihydrophenanthrene from cis-stilbene have been measured in cyclohexane, hexane, acetonitrile, and methanol solvents. Degassed cis-stilbene samples at 27-degrees-C were irradiated at 280 nm, and the formation of photoproducts was monitored by absorption spectroscopy. The quantum yield for formation of dihydrophenanthrene is two to three times greater in the nonpolar solvents than in the polar ones (15-19% vs 5-8%), while a slight solvent dependence of the yield of trans-stilbene is observed (35-39% in the polar solvents vs 32-35% in the hydrocarbons). Ground-state resonance Raman spectra of cis-stilbene have also been obtained with 266-nm excitation in each of the four solvents in order to probe the initial dynamics of nuclear motion in the Franck-Condon region. The intensities suggest very slightly faster distortion of the vertically excited state along out-of-plane and hydrogen wagging and rocking coordinates in polar relative to nonpolar solvents. The implications for the dynamics of the cis-trans isomerization and ring closure reactions are discussed.
• Synthesis of Derivatives of Phenanthrene and Helicene by Improved Procedures of Photocyclization of Stilbenes
  作者：Harish R. Talele、Monik J. Gohil、Ashutosh V. Bedekar

  DOI：10.1246/bcsj.82.1182

  日期：2009.9.15

  An improved method has been developed for photocyclization of stilbene to construct phenanthrenes and benzo[c]phenanthrenes. This reaction is promoted by iodine while tetrahydrofuran is used as an ...

  已经开发了一种改进的方法，用于二苯乙烯的光环化以构建菲和苯并 [c] 菲。该反应由碘促进，而四氢呋喃用作...