N-(p-Dimethylaminophenyl)-9,10-dihydro-9,10-ethanoanthracen-1',2'-dicarboximid | 19392-50-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: N-(p-Dimethylaminophenyl)-9,10-dihydro-9,10-ethanoanthracen-1',2'-dicarboximid
• 英文别名: N-(p-Dimethylaminophenyl)-9,10-dihydro-9,10-ethanoanthracen-11,12-dicarboximid；(9s,10s)-13-(4-(dimethylamino)phenyl)-10,11-dihydro-9H-9,10-[3,4]epipyrroloanthracene-12,14(13H,15H)-dione；17-[4-(dimethylamino)phenyl]-17-azapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaene-16,18-dione
• CAS: 19392-50-8
• 化学式: C₂₆H₂₂N₂O₂
• 分子量: 394.473
• InChiKey: ZDALZQKLGWKQRU-UHFFFAOYSA-N

物化性质

• 沸点：
  658.9±55.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(p-Dimethylaminophenyl)-9,10-dihydro-9,10-ethanoanthracen-1',2'-dicarboximid 以 间二甲苯 、 乙腈 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Photoactivatable Anthracenes

  摘要：

  Fifteen substituted maleimide cycloadducts of anthracene derivatives were synthesized in one or two steps from available precursors in yields ranging from 32 to 63%. They differ in the nature of the group on the maleimide nitrogen atom and of the substituents on the anthracene platform. In all instances, the introduction of a maleimide bridge across positions 9 and 10 of the anthracene skeleton isolates electronically its peripheral phenylene rings and suppresses its characteristic fluorescence. The cycloadducts with a 4-(dimethylamino)phenyl group on the maleimide nitrogen atom undergo retro-cycloaddition upon ultraviolet illumination with quantum yields ranging from 0.001 to 0.01. This structural transformation restores the aromatic character of the central ring of the oligoacene chromophore and activates its emission with fluorescence quantum yields ranging from 0.07 to 0.85. Thus, this particular choice of building blocks for the construction of photoresponsive compounds can translate into viable operating principles for fluorescence activation and, ultimately, lead to the realization of valuable photoactivatable fluorophores for imaging applications.

  DOI：

  10.1021/jo5004482
• 作为产物：
  描述：

  dibenzobarallene 、 N,N-二甲基-对苯二胺 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以60%的产率得到N-(p-Dimethylaminophenyl)-9,10-dihydro-9,10-ethanoanthracen-1',2'-dicarboximid
  参考文献：
  名称：

  Photoactivatable Anthracenes

  摘要：

  Fifteen substituted maleimide cycloadducts of anthracene derivatives were synthesized in one or two steps from available precursors in yields ranging from 32 to 63%. They differ in the nature of the group on the maleimide nitrogen atom and of the substituents on the anthracene platform. In all instances, the introduction of a maleimide bridge across positions 9 and 10 of the anthracene skeleton isolates electronically its peripheral phenylene rings and suppresses its characteristic fluorescence. The cycloadducts with a 4-(dimethylamino)phenyl group on the maleimide nitrogen atom undergo retro-cycloaddition upon ultraviolet illumination with quantum yields ranging from 0.001 to 0.01. This structural transformation restores the aromatic character of the central ring of the oligoacene chromophore and activates its emission with fluorescence quantum yields ranging from 0.07 to 0.85. Thus, this particular choice of building blocks for the construction of photoresponsive compounds can translate into viable operating principles for fluorescence activation and, ultimately, lead to the realization of valuable photoactivatable fluorophores for imaging applications.

  DOI：

  10.1021/jo5004482

文献信息

• Photoactivatable Anthracenes
  作者：Ek Raj Thapaliya、Burjor Captain、Françisco M. Raymo

  DOI：10.1021/jo5004482

  日期：2014.5.2

  Fifteen substituted maleimide cycloadducts of anthracene derivatives were synthesized in one or two steps from available precursors in yields ranging from 32 to 63%. They differ in the nature of the group on the maleimide nitrogen atom and of the substituents on the anthracene platform. In all instances, the introduction of a maleimide bridge across positions 9 and 10 of the anthracene skeleton isolates electronically its peripheral phenylene rings and suppresses its characteristic fluorescence. The cycloadducts with a 4-(dimethylamino)phenyl group on the maleimide nitrogen atom undergo retro-cycloaddition upon ultraviolet illumination with quantum yields ranging from 0.001 to 0.01. This structural transformation restores the aromatic character of the central ring of the oligoacene chromophore and activates its emission with fluorescence quantum yields ranging from 0.07 to 0.85. Thus, this particular choice of building blocks for the construction of photoresponsive compounds can translate into viable operating principles for fluorescence activation and, ultimately, lead to the realization of valuable photoactivatable fluorophores for imaging applications.