3-[(4-丁基苯基)甲氧基]苯-1,2-二腈 | 158475-59-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-[(4-丁基苯基)甲氧基]苯-1,2-二腈
• 英文名称: 3-p-butylbenzyloxyphthalonitrile
• 英文别名: 3-[(4-Butylphenyl)methoxy]benzene-1,2-dicarbonitrile；3-[(4-butylphenyl)methoxy]benzene-1,2-dicarbonitrile
• CAS: 158475-59-3
• 化学式: C₁₉H₁₈N₂O
• 分子量: 290.365
• InChiKey: PENJPDXEMYZRRI-UHFFFAOYSA-N

物化性质

• 熔点：
  70-71 °C
• 沸点：
  487.7±45.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 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-[(4-丁基苯基)甲氧基]苯-1,2-二腈 在 辛醇 、 lithium 作用下， 以 四氢呋喃 为溶剂， 以40%的产率得到1,8,15,22-tetra(p-n-butylbenzyloxy)phthalocyanine
  参考文献：
  名称：

  The syntheses of 2,9,16,23- and 1,8,15,22-tetrahydroxyphthalocyanines

  摘要：

  从适当的邻苯二腈合成了2,9,16,23-四-p-正丁基苄氧基-、2,9,16,23-四二苯甲氧基-、2,9,16,23-四甲氧基甲氧基-和1,8,15,22-四-p-正丁基苄氧基酞菁。无金属酞菁转化为其锌衍生物。用三氟乙酸从适当的前体中裂解产生2,9,16,23-四羟基酞菁和1,8,15,22-四羟基酞菁及其锌衍生物。核磁共振光谱显示，所有2,9,16,23-四取代酞菁都是通常的2,9,16,23、2,9,16,24、2,9,17,24和2,10,16,24异构体的混合物，但两个1,8,15,22-四取代酞菁是纯单一异构体形成的。

  DOI：

  10.1139/v94-254
• 作为产物：
  描述：

  3-硝基邻苯二腈 、 对丁基苯甲醇 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 156.0h， 以95%的产率得到3-[(4-丁基苯基)甲氧基]苯-1,2-二腈
  参考文献：
  名称：

  The syntheses of 2,9,16,23- and 1,8,15,22-tetrahydroxyphthalocyanines

  摘要：

  从适当的邻苯二腈合成了2,9,16,23-四-p-正丁基苄氧基-、2,9,16,23-四二苯甲氧基-、2,9,16,23-四甲氧基甲氧基-和1,8,15,22-四-p-正丁基苄氧基酞菁。无金属酞菁转化为其锌衍生物。用三氟乙酸从适当的前体中裂解产生2,9,16,23-四羟基酞菁和1,8,15,22-四羟基酞菁及其锌衍生物。核磁共振光谱显示，所有2,9,16,23-四取代酞菁都是通常的2,9,16,23、2,9,16,24、2,9,17,24和2,10,16,24异构体的混合物，但两个1,8,15,22-四取代酞菁是纯单一异构体形成的。

  DOI：

  10.1139/v94-254

文献信息

• The syntheses of 2,9,16,23- and 1,8,15,22-tetrahydroxyphthalocyanines
  作者：Clifford C. Leznoff、Mougang Hu、Colin R. McArthur、Yongnian Qin、Johan E. van Lier

  DOI：10.1139/v94-254

  日期：1994.9.1

  2,9,16,23-Tetra-p-n-butylbenzyloxy-, 2,9,16,23-tetradiphenylmethoxy-, 2,9,16,23-tetramethoxymethoxy-, and 1,8,15,22-tetra-p-n-butylbenzyloxyphthalocyanines were synthesized from the appropriate phthalonitriles. Metal-free phthalocyanines were converted to their zinc derivatives. Cleavage from the appropriate precursor with trifluoroacetic acid produced 2,9,16,23-tetrahydroxyphthalocyanine and 1,8,15,22-tetrahydroxyphthalocyanine and their zinc derivatives. NMR spectroscopy revealed that all the 2,9,16,23-tetrasubstituted phthalocyanines are the usual mixtures of the 2,9,16,23, 2,9,16,24, 2,9,17,24, and 2,10,16,24 isomers, but the two 1,8,15,22-tetrasubstituted phthalocyanines were formed as pure single isomers.

  从适当的邻苯二腈合成了2,9,16,23-四-p-正丁基苄氧基-、2,9,16,23-四二苯甲氧基-、2,9,16,23-四甲氧基甲氧基-和1,8,15,22-四-p-正丁基苄氧基酞菁。无金属酞菁转化为其锌衍生物。用三氟乙酸从适当的前体中裂解产生2,9,16,23-四羟基酞菁和1,8,15,22-四羟基酞菁及其锌衍生物。核磁共振光谱显示，所有2,9,16,23-四取代酞菁都是通常的2,9,16,23、2,9,16,24、2,9,17,24和2,10,16,24异构体的混合物，但两个1,8,15,22-四取代酞菁是纯单一异构体形成的。
• The synthesis of phthalocyanines at room temperature
  作者：Clifford C. Leznoff、Mougang Hu、Kieran J. M. Nolan

  DOI：10.1039/cc9960001245

  日期：——

  Condensation of 4-substituted phthalonitriles with lithium 2-N,N-dimethylaminoethoxide in 2-N,N-dimethylamino-ethanol gives a non-statistical mixture of tetrasubstituted phthalocyanines at room temperature or lower while 3-substituted phthalonitriles similarly condense with lithium octan-1-olate in octan-1-ol giving 1,8,15,22-tetra-substituted phthalocyanines as pure isomers.

  在室温或更低的温度下，4-取代酞腈与 2-N,N-二甲氨基乙醇中的 2-N,N-二甲氨基乙醇锂缩合，会产生四取代酞菁的非统计混合物，而 3-取代酞腈与辛烷-1-醇中的辛烷-1-醇酸锂缩合，同样会产生 1,8,15,22-四取代酞菁的纯异构体。
• 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.