4,5-双(苯基甲氧基)-1,2-苯二甲腈 | 206995-45-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4,5-双(苯基甲氧基)-1,2-苯二甲腈
• 中文别名: 4,5-双(苄氧基)邻苯二甲腈
• 英文名称: 4,5-dibenzyloxyphthalonitrile
• 英文别名: 1,2-dibenzyloxy-4,5-dicyanobenzene；4,5-Bis(benzyloxy)phthalonitrile；4,5-bis(phenylmethoxy)benzene-1,2-dicarbonitrile
• CAS: 206995-45-1
• 化学式: C₂₂H₁₆N₂O₂
• 分子量: 340.381
• InChiKey: GKXPEJISVXRJBA-UHFFFAOYSA-N

物化性质

• 熔点：
  183.5-184.5 °C
• 沸点：
  561.8±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  4,5-双(苯基甲氧基)-1,2-苯二甲腈 在 samarium(III) acetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 正己醇 为溶剂， 以47%的产率得到samarium(III) 2,3,9,10,16,17,23,24,2',3',9',10',16',17',23',24'-hexadecabenzyloxy(diphthalocyanine)
  参考文献：
  名称：

  稀土元素的十六苄氧基（二酞菁）：合成、光谱和电化学特性

  摘要：

  4,5-二苄氧基邻苯二甲腈与稀土元素的盐反应生成对称的镥、镝、钐和钕与十六苄氧基（二酞菁）的配合物，这些配合物在有机溶剂中具有良好的溶解性。研究了所得配合物的光谱和电化学特性。

  DOI：

  10.1007/s11172-006-0082-9
• 作为产物：
  描述：

  2-苄基-2,4-环己二酮 在 溴 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 4,5-双(苯基甲氧基)-1,2-苯二甲腈
  参考文献：
  名称：

  Hydroxyphthalocyanines as Potential Photodynamic Agents for Cancer Therapy

  摘要：

  A series of benzyl-substituted phthalonitriles, substituted at the 3-, 4-, and 4,5-positions, underwent varied condensations with phthalonitrile to give a series of protected (monohydroxy- and polyhydroxyphthalocyaninato)zinc(II) derivatives which were readily cleaved to give several hydroxyphthalocyanines (ZnPc) (phthalocyanine phenol analogues). Their efficacy as sensitizers for the photodynamic therapy (PDT) of cancer was evaluated on the EMT-B mammary tumor cell line. In vitro, the 2-hydroxy ZnPc (32) was the most active, followed by the 2,3- and 2,9-dihydroxy ZnPc (39 and 45), with the 2,9,16-trihydroxy ZnPc (33) exhibiting the least activity. In vivo, the monohydroxy derivative 32 and the 2,3-dihydroxy derivative 39 were both efficient in inducing tumor necrosis at 1 mu mol kg(-1), but complete tumor regression was poor, even at 2 mu mol/kg. In contrast, the 2,9-dihydroxy isomer 45, at 2 mu mol kg(-1), induced tumor necrosis in all animals treated, with 75% complete regression. These results underline the importance of the position of the substituents on the Pc macrocycle to optimize tumor response and confirm the PDT potential of the unsymmetrical Pcs bearing functional groups on adjacent benzene rings.

  DOI：

  10.1021/jm970336s

文献信息

• Synthesis of Crowned Triazolephthalocyanines
  作者：Beatriz Cabezón、Ernesto Quesada、Sagrario Esperanza、Tomás Torres

  DOI：10.1002/1099-0690(200008)2000:15<2767::aid-ejoc2767>3.0.co;2-2

  日期：2000.8

  The synthesis of triazolephthalocyanines bearing crown ether and aza-crown ether substituents is described. Different substituents have been introduced on the nitrogen atom of the aza-crown moiety to improve the solubility and the intrinsic amphiphilic character of these macrocycles. The crowned triazolephthalocyanines described have been prepared by a statistical procedure, and also by different variations

  描述了带有冠醚和氮杂冠醚取代基的三唑酞菁的合成。在氮杂冠部分的氮原子上引入了不同的取代基，以提高这些大环的溶解度和固有的两亲性。所描述的加冠三唑酞菁已通过统计程序以及逐步方法的不同变体制备。还对这一新化合物家族的一个代表的聚集特性进行了初步研究。展示了对三唑酞菁的相应二氰基衍生物前体合成的详尽研究。为此目的使用了两种不同的方法：第一种方法在合成冠醚部分之前插入氰基，而第二个在氰化过程之前构建分子的冠醚部分。Rosemund-von-Braun氰化条件的不相容性和分子中氮原子的存在是这些前体合成的主要难点。
• A Biotinylated and Endoplasmic Reticulum-Targeted Glutathione-Responsive Zinc(II) Phthalocyanine for Targeted Photodynamic Therapy
  作者：Ligang Yu、Qiong Wang、Ka-Wing Yeung、Wing-Ping Fong、Pui-Chi Lo

  DOI：10.1002/asia.201800852

  日期：2018.11.16

  A biotinylated glutathione (GSH)‐responsive zinc(II) phthalocyanine has been prepared and characterized. With a 2,4‐dinitrobenzenesulfonyl moiety, its fluorescence emission and singlet oxygen generation were silenced in its intact state. Upon exposure to high concentration of GSH, its photosensitizing properties were restored in phosphate buffered saline and inside tumor cells. It also showed preferential

  已经制备并表征了生物素化的谷胱甘肽（GSH）响应性锌（II）酞菁。带有2,4-二硝基苯磺酰基部分，其荧光发射和单线态氧的产生在其完整状态下被沉默。暴露于高浓度的GSH后，其光敏特性在磷酸盐缓冲液和肿瘤细胞内部得以恢复。它还显示优先摄取人类肝癌HepG2细胞（具有较高的生物素受体表达），而不是中国仓鼠卵巢（CHO）细胞（具有较低的生物素受体表达）。在照射时，就引起photocytotoxicity与IC 50值低至0.1μ米对HepG2细胞。此外，它可以定位在内质网（ER）中，在光照射后引起ER应力。
• Hexadecabenzyloxy(diphthalocyanines) of rare-earth elements: synthesis and spectroscopic and electrochemical characteristics
  作者：I. P. Kalashnikova、I. V. Zhukov、L. G. Tomilova、N. S. Zefirov

  DOI：10.1007/s11172-006-0082-9

  日期：2005.9

  elements afforded symmetrical lutetium, dysprosium, samarium, and neodymium complexes with hexadecabenzyloxy(diphthalocyanine), which are well soluble in organic solvents. The spectroscopic and electrochemical characteristics of the complexes obtained were studied.

  4,5-二苄氧基邻苯二甲腈与稀土元素的盐反应生成对称的镥、镝、钐和钕与十六苄氧基（二酞菁）的配合物，这些配合物在有机溶剂中具有良好的溶解性。研究了所得配合物的光谱和电化学特性。
• Hydroxyphthalocyanines as Potential Photodynamic Agents for Cancer Therapy
  作者：Mougang Hu、Nicole Brasseur、S. Zeki Yildiz、Johan E. van Lier、Clifford C. Leznoff

  DOI：10.1021/jm970336s

  日期：1998.5.1

  A series of benzyl-substituted phthalonitriles, substituted at the 3-, 4-, and 4,5-positions, underwent varied condensations with phthalonitrile to give a series of protected (monohydroxy- and polyhydroxyphthalocyaninato)zinc(II) derivatives which were readily cleaved to give several hydroxyphthalocyanines (ZnPc) (phthalocyanine phenol analogues). Their efficacy as sensitizers for the photodynamic therapy (PDT) of cancer was evaluated on the EMT-B mammary tumor cell line. In vitro, the 2-hydroxy ZnPc (32) was the most active, followed by the 2,3- and 2,9-dihydroxy ZnPc (39 and 45), with the 2,9,16-trihydroxy ZnPc (33) exhibiting the least activity. In vivo, the monohydroxy derivative 32 and the 2,3-dihydroxy derivative 39 were both efficient in inducing tumor necrosis at 1 mu mol kg(-1), but complete tumor regression was poor, even at 2 mu mol/kg. In contrast, the 2,9-dihydroxy isomer 45, at 2 mu mol kg(-1), induced tumor necrosis in all animals treated, with 75% complete regression. These results underline the importance of the position of the substituents on the Pc macrocycle to optimize tumor response and confirm the PDT potential of the unsymmetrical Pcs bearing functional groups on adjacent benzene rings.