2-(trans-7,8-Dichlorodibenzobicyclo<2.2.2>octadienyl)ethyl Ethanoate | 131567-38-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: 2-(trans-7,8-Dichlorodibenzobicyclo<2.2.2>octadienyl)ethyl Ethanoate
• 英文别名: 2-(trans-7,8-Dichlorodibenzobicyclo[2.2.2]octadienyl)ethyl Ethanoate
• CAS: 131567-38-9
• 化学式: C₂₀H₁₈Cl₂O₂
• 分子量: 361.268
• InChiKey: LALABDQEGHJCLS-VNTMZGSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(trans-7,8-Dichlorodibenzobicyclo<2.2.2>octadienyl)ethyl Ethanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以60%的产率得到2-(trans-7,8-Dichlorodibenzobicyclo<2.2.2>octadienyl)ethanol
  参考文献：
  名称：

  Substituent effects on regioselectivities in elimination reactions of bridgehead-substituted 7,8-dichlorodibenzobicyclo[2.2.2]octadienes

  摘要：

  The syntheses and dehydrochlorinations of a number of bridgehead-substituted 7,8-dichlorodibenzobicyclo-[2.2.2]octadienes are described. The bridgehead substituents (and corresponding substrates) include (CH2)2CO2H (14b), (CH2)3OCH3 (16), CH2OCH3 (17), (CH2)3OH (12), (CH2)2OH (20), and CH2OH (22). Base-induced dehydrochlorinations of 14b yield predominantly vinyl chloride resulting from base attack on H at C-8 (remote from the carboxylate anion) similar to observations in previous related studies. Dehydrochlorinations of 16 and 17 yielded the isomeric vinyl chlorides with almost complete loss of regioselectivity. Dehydrochlorinations of 12 and 20 (and to a lesser extent with 22) proceeded with high regioselectivity opposite to that observed for 14b. These results suggest the intervention of intramolecular base-induced eliminations from 12 and 20 and to a lesser degree with 22.

  DOI：

  10.1021/jo00004a007
• 作为产物：
  描述：

  反-1,2-二氯乙烯 、 2-(9-Anthracenyl)ethyl Ethanoate 在 2,6-二叔丁基苯酚 作用下， 以 苯 为溶剂， 反应 62.0h， 以26%的产率得到2-(trans-7,8-Dichlorodibenzobicyclo<2.2.2>octadienyl)ethyl Ethanoate
  参考文献：
  名称：

  Substituent effects on regioselectivities in elimination reactions of bridgehead-substituted 7,8-dichlorodibenzobicyclo[2.2.2]octadienes

  摘要：

  The syntheses and dehydrochlorinations of a number of bridgehead-substituted 7,8-dichlorodibenzobicyclo-[2.2.2]octadienes are described. The bridgehead substituents (and corresponding substrates) include (CH2)2CO2H (14b), (CH2)3OCH3 (16), CH2OCH3 (17), (CH2)3OH (12), (CH2)2OH (20), and CH2OH (22). Base-induced dehydrochlorinations of 14b yield predominantly vinyl chloride resulting from base attack on H at C-8 (remote from the carboxylate anion) similar to observations in previous related studies. Dehydrochlorinations of 16 and 17 yielded the isomeric vinyl chlorides with almost complete loss of regioselectivity. Dehydrochlorinations of 12 and 20 (and to a lesser extent with 22) proceeded with high regioselectivity opposite to that observed for 14b. These results suggest the intervention of intramolecular base-induced eliminations from 12 and 20 and to a lesser degree with 22.

  DOI：

  10.1021/jo00004a007