9-hydroxy-10,10-dimethyl-9-vinyl-9,10-dihydrophenanthrene | 908120-98-9

• 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: 9-hydroxy-10,10-dimethyl-9-vinyl-9,10-dihydrophenanthrene
• CAS: 908120-98-9
• 化学式: C₁₈H₁₈O
• 分子量: 250.34
• InChiKey: YKAZYQBSJNIONY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  9-hydroxy-10,10-dimethyl-9-vinyl-9,10-dihydrophenanthrene 在 SOCl₂F 、 氟磺酸 作用下， 以 二氯甲烷-D2 为溶剂， 生成 6,6-dimethyl-4,5-dihydro-6H-cyclopenta[1,2,3-de]phenanthren-5a-ium fluorosulfonate
  参考文献：
  名称：

  可检测的9,10-二甲基-9-乙烯基菲an离子的简并重排：乙烯基的1,2-位移

  摘要：

  Dynamic NMR study showed that 9.10-dimethyl-9-vinylphenanthrenium ion, generated under the conditions ensuring its "long life." undergoes very fast (Delta G(not equal) = 24.4 kJ/mol at -103 degrees C) degenerate 1,2-shift of the vinyl group. According to the DFT quantum-chemical calculations, the process is one-step, and the low energy of formation of the activated complex is determined by effective participation of 71 electrons of the vinyl group in delocalization of the positive charge; no such delocalization is intrinsic to the initial ion.

  DOI：

  10.1134/s1070428006010155
• 作为产物：
  描述：

  10,10-二甲基菲-9-酮 、 乙烯基溴化镁 以 四氢呋喃 为溶剂， 反应 2.0h， 以50%的产率得到9-hydroxy-10,10-dimethyl-9-vinyl-9,10-dihydrophenanthrene
  参考文献：
  名称：

  可检测的9,10-二甲基-9-乙烯基菲an离子的简并重排：乙烯基的1,2-位移

  摘要：

  Dynamic NMR study showed that 9.10-dimethyl-9-vinylphenanthrenium ion, generated under the conditions ensuring its "long life." undergoes very fast (Delta G(not equal) = 24.4 kJ/mol at -103 degrees C) degenerate 1,2-shift of the vinyl group. According to the DFT quantum-chemical calculations, the process is one-step, and the low energy of formation of the activated complex is determined by effective participation of 71 electrons of the vinyl group in delocalization of the positive charge; no such delocalization is intrinsic to the initial ion.

  DOI：

  10.1134/s1070428006010155