9-Chloromethyl-8-trifluoromethyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-one | 294181-11-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 9-Chloromethyl-8-trifluoromethyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-one
• CAS: 294181-11-6
• 化学式: C₁₇H₁₅ClF₃NO₂
• 分子量: 357.76
• InChiKey: AKXVGHRIBXXWKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  33.45
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  氮杂-12-冠醚-4 、 9-Chloromethyl-8-trifluoromethyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-one 在 copper(I) bromide 吡啶 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以15%的产率得到8-Trifluoromethyl-9-(1,4,7-trioxa-10-aza-cyclododec-10-ylmethyl)-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-one
  参考文献：
  名称：

  离子响应性荧光化合物。4.阳离子结合对与单氮杂和二氮杂-皇冠醚连接的香豆素光物理性质的影响

  摘要：

  The properties of fluoroionophores consisting of coumarin 153 linked to monoaza-12-crown-4, monoaza-15-crown-5, and diaza-18-crown-6 are described. The photophysical changes upon complexation with alkali and alkaline-earth metal cations can be described in terms of enhancement of the intramolecular charge transfer in the coumarin dye owing to the direct interaction between the bound cation and the carbonyl group of the coumarin. The magnitude of the photophysical changes is controlled by the charge density of the bound cation. In the case of the diaza-18-crown-6 linked to two coumarins, an interesting specific increase of the fluorescence quantum yield upon binding of potassium and barium ions is observed. The high stability constants of the complexes arise from the participation of the carbonyl group of the coumarin into the complexes and from the deconjugation of the nitrogen atom of the aza-crown ether from the pi-electron system.

  DOI：

  10.1021/j100119a050
• 作为产物：
  描述：

  10-Oxo-8-trifluoromethyl-2,3,5,6-tetrahydro-1H,4H,10H-11-oxa-3a-aza-benzo[de]anthracene-9-carbaldehyde 在 吡啶 、 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 9-Chloromethyl-8-trifluoromethyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-one
  参考文献：
  名称：

  离子响应性荧光化合物。4.阳离子结合对与单氮杂和二氮杂-皇冠醚连接的香豆素光物理性质的影响

  摘要：

  The properties of fluoroionophores consisting of coumarin 153 linked to monoaza-12-crown-4, monoaza-15-crown-5, and diaza-18-crown-6 are described. The photophysical changes upon complexation with alkali and alkaline-earth metal cations can be described in terms of enhancement of the intramolecular charge transfer in the coumarin dye owing to the direct interaction between the bound cation and the carbonyl group of the coumarin. The magnitude of the photophysical changes is controlled by the charge density of the bound cation. In the case of the diaza-18-crown-6 linked to two coumarins, an interesting specific increase of the fluorescence quantum yield upon binding of potassium and barium ions is observed. The high stability constants of the complexes arise from the participation of the carbonyl group of the coumarin into the complexes and from the deconjugation of the nitrogen atom of the aza-crown ether from the pi-electron system.

  DOI：

  10.1021/j100119a050