5-(9-anthracenyl)-2-methylbenzaldehyde | 197780-82-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 5-(9-anthracenyl)-2-methylbenzaldehyde
• 英文别名: 5-anthracen-9-yl-2-methylbenzaldehyde
• CAS: 197780-82-8
• 化学式: C₂₂H₁₆O
• 分子量: 296.368
• InChiKey: VEGDAGLBHQSIGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.78
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  5-(9-anthracenyl)-2-methylbenzaldehyde 在 sodium methylate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 1.25h， 生成 1-methyl-2-styryl-4-triptycylbenzene
  参考文献：
  名称：

  New Molecular Devices:  In Search of a Molecular Ratchet

  摘要：

  The triptycene-substituted [3]- and [4]helicenes 1 and 2 were examined as possible molecular versions of mechanical ratchets, where the triptycene serves as the ratchet wheel and the helicenes as pawl and spring. The syntheses of 1 and 2b are described. H-1 NMR was employed to examine rotation around the triptycene/helicene single bond; at 20 degrees C rotation is frozen for both 1 and 2b, but the NMR of 1 revealed a plane of symmetry, indicating that 1 cannot function as a unidirectional ratchet. In contrast, NMR revealed that, like a ratchet, triptycyl[4]helicene 2b lacks the symmetry of 1 and has a barrier to rotation of 24.5 kcal/mol, but spin polarization transfer NMR experiments indicated the triptycene in 2b nonetheless rotates equally in both directions. That outcome is rationalized from the standpoint of thermodynamics.

  DOI：

  10.1021/jo9723218
• 作为产物：
  描述：

  5-溴-2-甲基苯甲醛 、 9-tri-n-butylstannylanthracene 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 60.0h， 以60%的产率得到5-(9-anthracenyl)-2-methylbenzaldehyde
  参考文献：
  名称：

  In Search of Molecular Ratchets

  摘要：

  DOI：

  10.1002/anie.199718661

文献信息

• In Search of Molecular Ratchets
  作者：T. Ross Kelly、Imanol Tellitu、José Pérez Sestelo

  DOI：10.1002/anie.199718661

  日期：1997.9.17
• New Molecular Devices:  In Search of a Molecular Ratchet
  作者：T. Ross Kelly、José Pérez Sestelo、Imanol Tellitu

  DOI：10.1021/jo9723218

  日期：1998.5.1

  The triptycene-substituted [3]- and [4]helicenes 1 and 2 were examined as possible molecular versions of mechanical ratchets, where the triptycene serves as the ratchet wheel and the helicenes as pawl and spring. The syntheses of 1 and 2b are described. H-1 NMR was employed to examine rotation around the triptycene/helicene single bond; at 20 degrees C rotation is frozen for both 1 and 2b, but the NMR of 1 revealed a plane of symmetry, indicating that 1 cannot function as a unidirectional ratchet. In contrast, NMR revealed that, like a ratchet, triptycyl[4]helicene 2b lacks the symmetry of 1 and has a barrier to rotation of 24.5 kcal/mol, but spin polarization transfer NMR experiments indicated the triptycene in 2b nonetheless rotates equally in both directions. That outcome is rationalized from the standpoint of thermodynamics.