3-(2-isopropyl-5-methylphenoxy)phthalonitrile | 853309-16-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2-isopropyl-5-methylphenoxy)phthalonitrile
• 英文别名: 3-[5-methyl-2-(propan-2-yl)phenoxy]benzene-1,2-dicarbonitrile；3-(5-Methyl-2-propan-2-ylphenoxy)benzene-1,2-dicarbonitrile
• CAS: 853309-16-7
• 化学式: C₁₈H₁₆N₂O
• 分子量: 276.338
• InChiKey: BWGLUZXPAVOSIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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-(2-isopropyl-5-methylphenoxy)phthalonitrile 在 copper diacetate 作用下， 以 戊醇 为溶剂， 以30%的产率得到copper 1,8(11),15(18),22(25)-tetra(2-isopropyl-5-methylphenoxy)phthalocyanine
  参考文献：
  名称：

  几种可溶性四苯氧基取代铜锌酞菁的合成与表征

  摘要：

  描述了带有苯氧基取代基的铜和锌酞菁 (Pcs) 的合成。制备 Pcs 9-16 所需的前体是通过空间位阻酚衍生物与 4-硝基邻苯二甲腈 (1) 或 3-硝基邻苯二甲腈 (2) 之间的亲核芳族取代反应制备的。得到的前体邻苯二甲腈在 DMAE 或 DBU 催化的 pentan-1-ol 中的环四聚得到所需的 Pcs，它们很好地溶于常见的有机溶剂，如氯仿和二氯甲烷。这些 Pcs 中的每一个都由四种结构异构体组成，并通过 1H NMR、UV/Vis、IR 和质谱以及元素分析进行​​表征，与所提出的结构一致。

  DOI：

  10.1055/s-2005-861795
• 作为产物：
  描述：

  百里酚 、 3-硝基邻苯二腈 在 lithium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 以81%的产率得到3-(2-isopropyl-5-methylphenoxy)phthalonitrile
  参考文献：
  名称：

  几种可溶性四苯氧基取代铜锌酞菁的合成与表征

  摘要：

  描述了带有苯氧基取代基的铜和锌酞菁 (Pcs) 的合成。制备 Pcs 9-16 所需的前体是通过空间位阻酚衍生物与 4-硝基邻苯二甲腈 (1) 或 3-硝基邻苯二甲腈 (2) 之间的亲核芳族取代反应制备的。得到的前体邻苯二甲腈在 DMAE 或 DBU 催化的 pentan-1-ol 中的环四聚得到所需的 Pcs，它们很好地溶于常见的有机溶剂，如氯仿和二氯甲烷。这些 Pcs 中的每一个都由四种结构异构体组成，并通过 1H NMR、UV/Vis、IR 和质谱以及元素分析进行​​表征，与所提出的结构一致。

  DOI：

  10.1055/s-2005-861795

文献信息

• Photodynamic inactivation of Enterococcus faecalis by conjugates of zinc(II) phthalocyanines with thymol and carvacrol loaded into lipid vesicles
  作者：Lukasz Sobotta、Sebastian Lijewski、Jolanta Dlugaszewska、Joanna Nowicka、Jadwiga Mielcarek、Tomasz Goslinski

  DOI：10.1016/j.ica.2019.02.031

  日期：2019.4

  Terpene-macrocycle conjugates, consisting of thymol or carvacrol and phthalocyanine were synthesized, characterized, and subjected to detailed optical and biological studies. The macrocyclization reactions of terpenesubstituted o-phthalonitrile derivatives were performed in a microwave reactor to give thymol- and carvacrolphthalocyanine conjugates, which were carefully purified by column chromatography and subsequently analyzed using HPLC and characterized using UV-Vis, NMR and MS. Both isolated phthalocyanine derivatives represent isomers of C-2v symmetry, which was confirmed by NMR study. The absorption UV-Vis spectra of studied thymol- and carvacrol-phthalocyanine conjugates with the Soret and the Q band possesses the same profile. Both molecules reveal emission in the red region of the spectrum with fluorescence quantum yields about two-fold lower in DMF and significantly lower in DMSO than that observed for zinc(II) phthalocyanine. The analyzed phthalocyanine derivatives generate singlet oxygen upon excitation with light at ca. three-fold lower level then that noticed for zinc(II) phthalocyanine. In comparison to zinc(II) phthalocyanine, both molecules also reveal two-fold lower photostability in DMF and similar stability in DMSO. Thymol- and carvacrol-phthalocyanine conjugates, zinc(II) phthalocyanine, thymol, and carvacrol were loaded into modified liposomes and subjected to biological activity study. Thymol-phthalocyanine conjugate at both 100 and 10 mu M revealed high, ca. 5 log photoinactivation potential on the growth of Enterococcus faecalis, similarly to reference zinc(II) phthalocyanine. For carvacrol-phthalocyanine conjugate, an increase of photoinactivation activity was observed at only 100 mu M in comparison to zinc(II) phthalocyanine, whereas a decrease at the concentration of 10 mu M was noticed. It is crucial that both studied phthalocyanines cross the border of 3 log photoinactivation potential, which indicates their bactericidal potential. In the Microtox (R) bioassay both conjugates revealed significantly decreased dark toxicity in comparison to thymol and carvacrol only. Interestingly, the carvacrol-phthalocyanine conjugate was found to be more toxic in comparison to thymol-phthalocyanine conjugate and zinc(II) phthalocyanine.