3-benzyloxyphthalonitrile | 206995-48-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-benzyloxyphthalonitrile
• 英文别名: 3-benzyloxy phthalodinitrile；1,2-Benzenedicarbonitrile, 3-(phenylmethoxy)-；3-phenylmethoxybenzene-1,2-dicarbonitrile
• CAS: 206995-48-4
• 化学式: C₁₅H₁₀N₂O
• 分子量: 234.257
• InChiKey: DMCSCRADMZTRBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzyloxyphthalonitrile 在 lithium 作用下， 以 various solvent(s) 为溶剂， 以42%的产率得到1,8,15,22-tetrakis(benzyloxy)phthalocyanine
  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
• 作为产物：
  描述：

  3-硝基邻苯二腈 、 苯甲醇 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以90%的产率得到3-benzyloxyphthalonitrile
  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

• Electrochemical characterisation of tetra- and octa-substituted oxo(phthalocyaninato)titanium(IV) complexes
  作者：Prudence Tau、Tebello Nyokong

  DOI：10.1016/j.electacta.2006.10.023

  日期：2007.3

  electrochemical characterisation of the following oxotitanium tetra-substituted phthalocyanines are reported: 1,(4)-(tetrabenzyloxyphthalocyaninato)titanium(IV) oxide (5a); 1,(4)-tetrakis[4-(benzyloxy)phenoxy]phthalocyaninato}titanium(IV) oxide (5b); 2,(3)-(tetrabenzyloxyphthalocyaninato)titanium(IV) oxide (6a) and 2,(3)-tetrakis[4-(benzyloxy)phenoxy]phthalocyaninato}titanium(IV) oxide (6b). The electrochemical

  报道了以下氧钛四取代的酞菁的合成和电化学表征：1，（4）-（四苄氧基酞菁萘）钛（IV）氧化物（5a）；1，（4）-四[4-（苄氧基）苯氧基]邻苯二甲酰氰基}氧化钛（IV）（5b）; 2，（3）-（四苄氧基邻苯二甲氧基酞菁钛）氧化物（6a）和2，（3）-四[4-（苄氧基）苯氧基]邻苯二甲酰氧基钛酞菁}（6b）。复合物的电化学表征辛取代4-（苄氧基）苯氧基（图9b），苯氧基（9C）和叔丁基苯氧基（9D）组也已报告。配合物的循环伏安图显示出可逆的偶对I – III，偶对IV对配合物5a，5b，6a和6b是准可逆的。前两次还原是基于金属的过程，通过光谱电化学证实是由于Ti IV Pc 2- / Ti III Pc 2-和Ti III Pc 2- / Ti II Pc 2-的氧化还原过程，最后两个还原是环- Ti II Pc 2- / Ti导致的基于过程的过程II Pc 3−和Ti II Pc 3−
• Liquid crystal display and colour filter with improved transparency for green light
  申请人：Keyzer De Gerardus

  公开号：US20060060829A1

  公开（公告）日：2006-03-23

  The invention relates to novel liquid crystal displays comprising a broad backlight emission around 530 nm and a green colour filter containing a phthalocyanine colorant, most adequately tetrahydroxy- or tetraalkoxy-substituted but lacking solubilizing groups.

  本发明涉及新型液晶显示器，该显示器具有 530 nm 左右的宽背光发射和含有酞菁着色剂的绿色滤色片，酞菁着色剂最好是四羟基或四烷氧基取代的，但缺乏增溶基团。
• [EN] LIQUID CRYSTAL DISPLAY AND COLOUR FILTER WITH IMPROVED TRANSPARENCY FOR GREEN LIGHT<br/>[FR] AFFICHEUR A CRISTAUX LIQUIDES ET FILTRE COULEUR PRESENTANT UNE TRANSPARENCE AMELIOREE A LA LUMIERE VERTE
  申请人：CIBA SC HOLDING AG

  公开号：WO2004018477A3

  公开（公告）日：2004-04-15
• LIQUID CRYSTAL DISPLAY AND COLOUR FILTER WITH IMPROVED TRANSPARENCY FOR GREEN LIGHT
  申请人：Ciba Specialty Chemicals Holding Inc.

  公开号：EP1534714A2

  公开（公告）日：2005-06-01
• US7582230B2
  申请人：——

  公开号：US7582230B2

  公开（公告）日：2009-09-01