5,6,6-trimethyl-4,6-dihydrocyclopenta[j,k]phenanthrene | 923057-77-6

• 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: 5,6,6-trimethyl-4,6-dihydrocyclopenta[j,k]phenanthrene
• 英文别名: 5,6,6-Trimethyl-4,6-dihydroacephenanthrylene；5,6,6-trimethyl-4H-acephenanthrylene
• CAS: 923057-77-6
• 化学式: C₁₉H₁₈
• 分子量: 246.352
• InChiKey: RUICILQKVRCSSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  9-isopropenyl-10,10-dimethyl-9,10-dihydrophenanthren-9-ol 在 三氟甲磺酸 、 sodium carbonate 作用下， 以 氯仿 、 甲醇 、 正己烷 为溶剂， 反应 0.5h， 以84%的产率得到5,6,6-trimethyl-4,6-dihydrocyclopenta[j,k]phenanthrene
  参考文献：
  名称：

  9-异丙烯基-9,10-二甲基菲基-9-基和9,10-二甲基-9-（反式-1-甲基丙-1-烯-1-基）菲基-9-基的简并重排

  摘要：

  H-1 NMR study has shown that long-lived 9-R-9,10-dimethylphenanthren-9-yl cations (R = isopropenyl, trans-1-methylprop-1-en-1-yl) generated in the system HSO3F-SO2ClF-CD2Cl2 at -130 degrees C undergo degenerate rearrangement via 1,2-vinyl shifts (Delta G(not equal) = 37 and 39 kJ/mol, respectively, at -88 degrees C). Analysis of the geometric parameters of the initial structures and transition states calculated by the DFT method indicates that unfavorable steric factors are responsible for the sharp deceleration of 1,2-shifts of the isopropenyl and trans-1-methylprop-1-en-1-yl groups as compared to vinyl and cis-1-methylprop-1-en-1-yl groups, respectively.

  DOI：

  10.1134/s1070428006090016

文献信息

• Degenerate rearrangement of 9-isopropenyl-9,10-dimethyl-phenanthren-9-yl and 9,10-dimethyl-9-(trans-1-methylprop-1-en-1-yl)phenanthren-9-yl cations
  作者：V. G. Artamoshkin、V. A. Bushmelev、A. M. Genaev、V. G. Shubin

  DOI：10.1134/s1070428006090016

  日期：2006.9

  H-1 NMR study has shown that long-lived 9-R-9,10-dimethylphenanthren-9-yl cations (R = isopropenyl, trans-1-methylprop-1-en-1-yl) generated in the system HSO3F-SO2ClF-CD2Cl2 at -130 degrees C undergo degenerate rearrangement via 1,2-vinyl shifts (Delta G(not equal) = 37 and 39 kJ/mol, respectively, at -88 degrees C). Analysis of the geometric parameters of the initial structures and transition states calculated by the DFT method indicates that unfavorable steric factors are responsible for the sharp deceleration of 1,2-shifts of the isopropenyl and trans-1-methylprop-1-en-1-yl groups as compared to vinyl and cis-1-methylprop-1-en-1-yl groups, respectively.