methyl 4-(6,7-dicyanonaphthalen-2-yloxy)benzoate | 1432736-07-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-(6,7-dicyanonaphthalen-2-yloxy)benzoate
• 英文别名: Methyl 4-(6,7-dicyanonaphthalen-2-yl)oxybenzoate；methyl 4-(6,7-dicyanonaphthalen-2-yl)oxybenzoate
• CAS: 1432736-07-6
• 化学式: C₂₀H₁₂N₂O₃
• 分子量: 328.327
• InChiKey: WYEPFLOFGWOJSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  正庚醇 、 methyl 4-(6,7-dicyanonaphthalen-2-yloxy)benzoate 、 zinc(II) acetate dihydrate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 3.0h， 以26%的产率得到[(4-heptyloxycarbonyl)phenoxy]₄-naphthalocyanine
  参考文献：
  名称：

  A naphthalocyanine based near-infrared photosensitizer: Synthesis and in vitro photodynamic activities

  摘要：

  A hydrophilic near-infrared (NIR) photosensitizer featuring a naphthalocyanine core and peripheral carboxylate acid groups was synthesized and characterized. Its photophysical and photochemical properties were studied and compared with phthalocyanine. Due to the extended pi-conjugation, both the Q band and fluorescence emit of this naphthalocyanine bathochromically shift to NIR region. It also exhibits superior NIR photodynamic efficiency to phthalocyanine as evidenced by high efficiency in generating singlet oxygen (Phi(Delta) = 0.66) and in vitro phototoxicity toward Hela human cervical cancer cells. Therefore, this novel naphthalocyanine could potentially be a NIR photosensitizer for photodynamic therapy. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.093
• 作为产物：
  描述：

  6-溴-2,3-二氰基萘 、 对羟基苯甲酸甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以22%的产率得到methyl 4-(6,7-dicyanonaphthalen-2-yloxy)benzoate
  参考文献：
  名称：

  A naphthalocyanine based near-infrared photosensitizer: Synthesis and in vitro photodynamic activities

  摘要：

  A hydrophilic near-infrared (NIR) photosensitizer featuring a naphthalocyanine core and peripheral carboxylate acid groups was synthesized and characterized. Its photophysical and photochemical properties were studied and compared with phthalocyanine. Due to the extended pi-conjugation, both the Q band and fluorescence emit of this naphthalocyanine bathochromically shift to NIR region. It also exhibits superior NIR photodynamic efficiency to phthalocyanine as evidenced by high efficiency in generating singlet oxygen (Phi(Delta) = 0.66) and in vitro phototoxicity toward Hela human cervical cancer cells. Therefore, this novel naphthalocyanine could potentially be a NIR photosensitizer for photodynamic therapy. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.093

文献信息

• A naphthalocyanine based near-infrared photosensitizer: Synthesis and in vitro photodynamic activities
  作者：Liqiang Luan、Lanlan Ding、Weijia Zhang、Jiawei Shi、Xiaoqiang Yu、Wei Liu

  DOI：10.1016/j.bmcl.2013.04.093

  日期：2013.7

  A hydrophilic near-infrared (NIR) photosensitizer featuring a naphthalocyanine core and peripheral carboxylate acid groups was synthesized and characterized. Its photophysical and photochemical properties were studied and compared with phthalocyanine. Due to the extended pi-conjugation, both the Q band and fluorescence emit of this naphthalocyanine bathochromically shift to NIR region. It also exhibits superior NIR photodynamic efficiency to phthalocyanine as evidenced by high efficiency in generating singlet oxygen (Phi(Delta) = 0.66) and in vitro phototoxicity toward Hela human cervical cancer cells. Therefore, this novel naphthalocyanine could potentially be a NIR photosensitizer for photodynamic therapy. (C) 2013 Elsevier Ltd. All rights reserved.