exo-2-cyano-5,6-benzobicyclo<2.2.2>octane | 83781-80-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: exo-2-cyano-5,6-benzobicyclo<2.2.2>octane
• 英文别名: exo-2-cyano-5,6-benzobicyclo[2.2.2]octane；(1S,8R,9R)-tricyclo[6.2.2.02,7]dodeca-2,4,6-triene-9-carbonitrile
• CAS: 83781-80-0；83830-11-9
• 化学式: C₁₃H₁₃N
• 分子量: 183.253
• InChiKey: QREZXDZDXBPRCI-JBLDHEPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  1-(trimethylsilyl)-4-(dimethylamino)-1,2,3,4-tetrahydronaphthalene 在 cesium fluoride 作用下， 以 乙腈 为溶剂， 生成 exo-2-cyano-5,6-benzobicyclo<2.2.2>octane
  参考文献：
  名称：

  Syntheses of polycyclic ring systems based on the new generation of o-quinodimethanes

  摘要：

  DOI：

  10.1021/ja00390a036

文献信息

• Reactivity and endo–exo Selectivity in Diels–Alder Reaction of o-Quinodimethanes. An Experimental and DFT Computational Study
  作者：Cristiana Di Valentin、Mauro Freccero、Mirko Sarzi-Amadè、Riccardo Zanaletti

  DOI：10.1016/s0040-4020(00)00126-5

  日期：2000.4

  endo-exo Selectivity in Diels-Alder cycloadditions of several o-quinodimethanes (1-4) with acrylonitrile, 2-(5H)-furanone and N-methylmaleimide has been investigated in acetonitrile solution. Transition structures of the cycloaddition of the parent o-QDM (1), (E,E)1,8-dimethyl-o-QDM (2), isoindene (3) and 2,3-dihydronaphthalene (4) with acrylonitrile and maleimide were located at both HF/6-31G* and B3LYP/6-31G* methods. Theoretical data reproduce fairly well both experimental absolute reaction rates and diastereoisomer ratios. The high endo selectivity has been rationalized mainly as a result of solvation effects (acetonitrile, PCM model) and reactant deformations. The latter is due to steric interactions. (C) 2000 Elsevier Science Ltd. All rights reserved.