1-(9-Anthryl)-2,2-dimesitylvinyl acetate | 153721-17-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-(9-Anthryl)-2,2-dimesitylvinyl acetate
• 英文别名: [1-Anthracen-9-yl-2,2-bis(2,4,6-trimethylphenyl)ethenyl] acetate
• CAS: 153721-17-6
• 化学式: C₃₆H₃₄O₂
• 分子量: 498.665
• InChiKey: LFWUIDDEPPDIGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-carboxybenzene diazonium chloride 、 1-(9-Anthryl)-2,2-dimesitylvinyl acetate 在 methyloxirane 作用下， 反应 3.0h， 生成 1-(9-Triptycyl)-2,2-dimesitylvinyl acetate
  参考文献：
  名称：

  Intramolecular Rotations in 2,2-Dimesityl-1-(9-anthryl)- and -1-(9-triptycyl)vinyl Acetates

  摘要：

  2,2-Dimesityl-1-(9-anthryl)vinyl acetate (3) and 2,2-dimesityl-1-(9-triptycyl)vinyl acetate (4) were prepared. The rotation of the mesityl and 9-anthryl rings in 3 and of the mesityl rings and triptycyl substituent in 4 around their bonds to the vinylic carbon were investigated by DNMR. For each system an identical rotational barrier was measured for each substituent, indicating a correlated rotation. The rotational barriers were 16.7 +/- 0.1 kcal mol(-1) for 3 and 17.0 +/- 0.1 kcal mol(-1) for 4. The suggested rotational mechanism is a three-ring flip for 3 and a correlated (geared) rotation for the three rotors of 4. The latter process involves a two-ring flip of the two mesityl rings and a rocking process of the triptycyl moiety in which only one of its rings eclipses the C=C plane in the transition state.

  DOI：

  10.1021/jo00086a015
• 作为产物：
  描述：

  9-溴蒽 在 吡啶 、 正丁基锂 作用下， 以 正己烷 为溶剂， 反应 14.17h， 生成 1-(9-Anthryl)-2,2-dimesitylvinyl acetate
  参考文献：
  名称：

  Intramolecular Rotations in 2,2-Dimesityl-1-(9-anthryl)- and -1-(9-triptycyl)vinyl Acetates

  摘要：

  2,2-Dimesityl-1-(9-anthryl)vinyl acetate (3) and 2,2-dimesityl-1-(9-triptycyl)vinyl acetate (4) were prepared. The rotation of the mesityl and 9-anthryl rings in 3 and of the mesityl rings and triptycyl substituent in 4 around their bonds to the vinylic carbon were investigated by DNMR. For each system an identical rotational barrier was measured for each substituent, indicating a correlated rotation. The rotational barriers were 16.7 +/- 0.1 kcal mol(-1) for 3 and 17.0 +/- 0.1 kcal mol(-1) for 4. The suggested rotational mechanism is a three-ring flip for 3 and a correlated (geared) rotation for the three rotors of 4. The latter process involves a two-ring flip of the two mesityl rings and a rocking process of the triptycyl moiety in which only one of its rings eclipses the C=C plane in the transition state.

  DOI：

  10.1021/jo00086a015

文献信息

• Intramolecular Rotations in 2,2-Dimesityl-1-(9-anthryl)- and -1-(9-triptycyl)vinyl Acetates
  作者：Etti Schottland、Joseph Frey、Zvi Rappoport

  DOI：10.1021/jo00086a015

  日期：1994.4

  2,2-Dimesityl-1-(9-anthryl)vinyl acetate (3) and 2,2-dimesityl-1-(9-triptycyl)vinyl acetate (4) were prepared. The rotation of the mesityl and 9-anthryl rings in 3 and of the mesityl rings and triptycyl substituent in 4 around their bonds to the vinylic carbon were investigated by DNMR. For each system an identical rotational barrier was measured for each substituent, indicating a correlated rotation. The rotational barriers were 16.7 +/- 0.1 kcal mol(-1) for 3 and 17.0 +/- 0.1 kcal mol(-1) for 4. The suggested rotational mechanism is a three-ring flip for 3 and a correlated (geared) rotation for the three rotors of 4. The latter process involves a two-ring flip of the two mesityl rings and a rocking process of the triptycyl moiety in which only one of its rings eclipses the C=C plane in the transition state.