4-(2-(azepan-1-yl)ethoxy)phthalonitrile | 1357148-25-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(2-(azepan-1-yl)ethoxy)phthalonitrile
• 英文别名: 4-[2-(Azepan-1-yl)ethoxy]benzene-1,2-dicarbonitrile；4-[2-(azepan-1-yl)ethoxy]benzene-1,2-dicarbonitrile
• CAS: 1357148-25-4
• 化学式: C₁₆H₁₉N₃O
• 分子量: 269.346
• InChiKey: DSUWZPNWVGHDCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-(azepan-1-yl)ethoxy)phthalonitrile 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 cobalt(II) chloride 作用下， 以 戊醇 为溶剂， 反应 48.0h， 生成 2,9,16,23-tetrakis(2-(azepan-1-yl)ethoxy)phthalocyaninatocobalt(II) 、 2,10,17,24-tetrakis(2-(azepan-1-yl)ethoxy)phthalocyaninatocobalt(II) 、 2,9,17,24-tetrakis(2-(azepan-1-yl)ethoxy)phthalocyaninatocobalt(II) 、 2,10,16,24-tetrakis(2-(azepan-1-yl)ethoxy)phthalocyaninatocobalt(II)
  参考文献：
  名称：

  Synthesis of new water soluble phthalocyanines and investigation of their photochemical, photophysical and biological properties

  摘要：

  With the quaternized derivatives (4a and 5a), the synthesis of new Zn(II) and Co(II) phthalocyanines (4 and 5) substituted with 2-(azepan-1-yl)ethoxy moieties are reported. Photochemical and photophysical properties of quaternized Zn(II) and Co(II) phthalocyanines (4a and 5a) are investigated in both dimethyl sulfoxide (DMSO) and water, while non ionic derivatives in DMSO only. General trends are described for fluorescence quantum yields, fluorescence lifetimes, singlet oxygen quantum yields and photodegradation quantum yields. In this work, the effect of substituents and the nature of the metal atoms on the photochemical and photophysical parameters of new phthalocyanines are discussed. The quaternized compounds exhibit excellent solubility in water, making them potential photosensitizers for use in photodynamic therapy (PDT) of cancer. This study also showed that the water-soluble quaternized Zn(II) phthalocyanines strongly bind to blood plasma proteins such as bovine serum albumin (BSA). (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2012.03.010
• 作为产物：
  描述：

  N-(2-羟乙基)六亚甲二胺 、 4-硝基邻苯二甲腈 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(2-(azepan-1-yl)ethoxy)phthalonitrile
  参考文献：
  名称：

  使用广谱纳米淬灭剂对细胞内蛋白水解级联进行多重成像

  摘要：

  把灯关掉！已经开发出一种通用纳米淬灭剂，通过将一系列暗淬灭剂掺入可渗透细胞的介孔二氧化硅纳米颗粒中，可以淬灭范围广泛的可见光至近红外染料。与染料标记的底物相结合，这种纳米淬灭剂在特定的蛋白水解作用下增强了多个荧光信号，从而可以对蛋白水解级联进行实时成像（参见方案）。

  DOI：

  10.1002/anie.201107795

文献信息

• Multiplex Imaging of an Intracellular Proteolytic Cascade by using a Broad-Spectrum Nanoquencher
  作者：Xinglu Huang、Magdalena Swierczewska、Ki Young Choi、Lei Zhu、Ashwinkumar Bhirde、Jinwoo Park、Kwangmeyung Kim、Jin Xie、Gang Niu、Kang Choon Lee、Seulki Lee、Xiaoyuan Chen

  DOI：10.1002/anie.201107795

  日期：2012.2.13

  A universal nanoquencher that quenches a broad range of visible to near‐infrared dyes by using a series of dark quenchers incorporated into a cell‐permeable mesoporous silica nanoparticle has been developed. In combination with dye‐labeled substrates, this nanoquencher boosts multiple fluorescence signals upon specific proteolysis, which allows real‐time imaging of proteolytic cascades (see scheme)

  把灯关掉！已经开发出一种通用纳米淬灭剂，通过将一系列暗淬灭剂掺入可渗透细胞的介孔二氧化硅纳米颗粒中，可以淬灭范围广泛的可见光至近红外染料。与染料标记的底物相结合，这种纳米淬灭剂在特定的蛋白水解作用下增强了多个荧光信号，从而可以对蛋白水解级联进行实时成像（参见方案）。
• Synthesis of new water soluble phthalocyanines and investigation of their photochemical, photophysical and biological properties
  作者：Canan Uslan、B. Şebnem Sesalan、Mahmut Durmuş

  DOI：10.1016/j.jphotochem.2012.03.010

  日期：2012.5

  With the quaternized derivatives (4a and 5a), the synthesis of new Zn(II) and Co(II) phthalocyanines (4 and 5) substituted with 2-(azepan-1-yl)ethoxy moieties are reported. Photochemical and photophysical properties of quaternized Zn(II) and Co(II) phthalocyanines (4a and 5a) are investigated in both dimethyl sulfoxide (DMSO) and water, while non ionic derivatives in DMSO only. General trends are described for fluorescence quantum yields, fluorescence lifetimes, singlet oxygen quantum yields and photodegradation quantum yields. In this work, the effect of substituents and the nature of the metal atoms on the photochemical and photophysical parameters of new phthalocyanines are discussed. The quaternized compounds exhibit excellent solubility in water, making them potential photosensitizers for use in photodynamic therapy (PDT) of cancer. This study also showed that the water-soluble quaternized Zn(II) phthalocyanines strongly bind to blood plasma proteins such as bovine serum albumin (BSA). (C) 2012 Elsevier B.V. All rights reserved.