4-(4-formyl-1-methoxyphenoxy)phthalonitrile | 893786-32-8

• 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: 4-(4-formyl-1-methoxyphenoxy)phthalonitrile
• 英文别名: 4-(4-formyl-2-methoxy-phenoxy)-phthalonitrile；1,2-Benzenedicarbonitrile, 4-(4-formyl-2-methoxyphenoxy)-；4-(4-formyl-2-methoxyphenoxy)benzene-1,2-dicarbonitrile
• CAS: 893786-32-8
• 化学式: C₁₆H₁₀N₂O₃
• 分子量: 278.267
• InChiKey: VJMLEJMWXLPTSA-UHFFFAOYSA-N

物化性质

• 沸点：
  492.8±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4-formyl-1-methoxyphenoxy)phthalonitrile 、 2-萘酚 在 对甲苯磺酸 作用下， 以 neat (no solvent) 为溶剂， 反应 0.33h， 生成 4-[4-(14H-dibenzo[a,j]xanthen-14-yl)-2-methoxyphenoxy]-phthalonitrile
  参考文献：
  名称：

  Synthesis and computational studies of new metallo-phthalocyanines bearing dibenzoxanthenes and evaluation of their optical properties in solution and solid PMMA/ZnPc/Al nanocomposite films

  摘要：

  成功合成了新型热稳定金属酞菁化合物，采用二苯并呋喃作为高度有机溶解的芳香烃取代基，通过与无水金属盐（[Zn(CH$_{3}$COO)$_{2}$ 和 NiCl$_{2}$）在2-(二甲基氨基)乙醇中添加催化剂DBU的情况下，循环四聚合得到。这些酞菁均可溶于一些有机溶剂，如DMF、DMSO、THF、CH$_{2}$Cl$_{2}$和CHCl$_{3}$。然后，我们成功地通过将铝纳米颗粒掺入透明的PMMA/ZnPc基体中制备了聚（甲基丙烯酸甲酯）（PMMA）/ZnPc/Al纳米复合膜。利用X射线衍射和扫描电子显微镜对纳米复合膜的结构和形态进行了研究。PMMA/ZnPc/Al纳米复合膜的光学吸收光谱显示出聚合物基体中Q带的红移。两个酞菁的几何结构在RHF/3-21G*计算水平下进行了研究。

  DOI：

  10.3906/kim-1509-28
• 作为产物：
  描述：

  4-氟邻苯二腈 、 香草醛 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以62%的产率得到4-(4-formyl-1-methoxyphenoxy)phthalonitrile
  参考文献：
  名称：

  Identification of Diaryl Ether-Based Ligands for Estrogen-Related Receptor α as Potential Antidiabetic Agents

  摘要：

  Estrogen-related receptor a (ERR alpha) is an orphan nuclear receptor that has been functionally implicated in the regulation of energy homeostasis. Herein is described the development of diaryl ether based thiazolidenediones, which function as selective ligands against this receptor. Series optimization provided several potent analogues that inhibit the recruitment of a coactivator peptide fragment in in vitro biochemical assays (IC50 < 150 nM) and cellular two-hybrid reporter assays against the ligand binding domain (IC50 = 1-5 mu M). A cocrystal structure of the ligand-binding domain of ERR alpha with lead compound 29 revealed the presence of a covalent interaction between the protein and ligand, which has been shown to be reversible. In diet-induced murine models of obesity and in an overt diabetic rat model, oral administration of 29 normalized insulin and circulating triglyceride levels, improved insulin sensitivity, and was body weight neutral. This provides the first demonstration of functional activities of an ERRa ligand in metabolic animal models.

  DOI：

  10.1021/jm101063h

文献信息

• Discotic liquid crystals of transition metal complexes 52: Synthesis and homeotropic alignment of liquid crystalline phthalocyanine-fullerene dyad bridged by vanillin
  作者：Ayumi Watarai、Kazuchika Ohta、Mikio Yasutake

  DOI：10.1142/s1088424616501194

  日期：2016.12

  We have synthesized a novel liquid crystalline phthalocyanine(Pc)-fullerene(C[Formula: see text] dyad (C[Formula: see text]S)[Formula: see text]PcCu-VAN-C[Formula: see text] (3a) bridged by an inexpensive natural product of vanillin (VAN), instead of the previous long [Formula: see text]-alkylene chain spacer. We have also synthesized a comparative dyad (C[Formula: see text]S)[Formula: see text]PcCu-OPh-C[Formula: see text] (3b) bridged by [Formula: see text]-hydroxybenzaldehyde (OPh), in order to investigate the influence of the methoxy group in the vanillin moiety on homeotropic alignment between two glass plates. Very interestingly, homeotropic alignment could be observed only for the dyad (C[Formula: see text]S)[Formula: see text]PcCu-VAN-C[Formula: see text] (3a) having a methoxy group in the vanillin moiety, whereas it could not be observed for the dyad (C[Formula: see text]S)[Formula: see text]PcCu-OPh-C[Formula: see text] (3b) having no methoxy group at the phenoxy group. It is very noteworthy that such a slight difference in these molecular structures between 3a and 3b becomes a crucial point to show the homeotropic alignment. Each of the dyads, 3a and 3b, showed two hexagonal ordered columnar (Col[Formula: see text] mesophases. Each of the Col[Formula: see text] mesophases in 3a and 3b gave an additional very strong reflection peak named as Peak H in a very low angle region of the SAXS (small angle X-ray scattering) pattern. Peak H could be established, from two different SAXS measurement methods, as one pitch in a helical structure of the fullerenes around the Pc column.

  我们合成了一种新型液晶酞菁（Pc）-fullerene(C[式：见正文]二元化合物（C[式：见正文]S）[式：见正文]PcCu-VAN-C[式：见正文](3a)，它由一种廉价的天然产物香兰素（VAN）桥接，而不是以前的长[式：见正文]烯链间隔物。我们还合成了一种由[式：见正文]-羟基苯甲醛（OPh）桥接的比较二元化合物（C[式：见正文]S）[式：见正文]PcCu-OPh-C[式：见正文]（3b），以研究香兰素分子中的甲氧基对两块玻璃板之间的同向排列的影响。有趣的是，只有在香兰素分子中含有甲氧基的二元化合物（C[式：见正文]S）[式：见正文]PcCu-VAN-C[式：见正文]（3a）才能观察到同向排列，而在苯氧基上没有甲氧基的二元化合物（C[式：见正文]S）[式：见正文]PcCu-OPh-C[式：见正文]（3b）则无法观察到同向排列。值得注意的是，3a 和 3b 在分子结构上的细微差别成为显示同向排列的关键点。3a 和 3b 的每个二元化合物都呈现出两个六方有序柱状（Col[式：见正文]介相）。3a 和 3b 中的每个 Col[式：见正文]介相都在 SAXS（小角 X 射线散射）图案的极低角度区域中产生了一个额外的强反射峰，称为峰 H。根据两种不同的 SAXS 测量方法，H 峰可以被确定为围绕 Pc 柱的富勒烯螺旋结构中的一个节距。
• 新型双邻苯二甲腈类化合物及其应用
  申请人：北京化工大学

  公开号：CN115368276A

  公开（公告）日：2022-11-22

  本发明提供了一种新型双邻苯二甲腈类化合物及其应用，该新型双邻苯二甲腈类化合物为含醛亚胺结构的双端基邻苯二甲腈类化合物，该化合物由于结构中含有柔性结构，其熔融温度显著降低，加工温度窗口拓宽，且由该化合物固化得到的固化物具有良好的耐热性能，适用于高温环境，主要用于高性能树脂、复合材料基体、粘合剂和涂层领域。
• Magnetite–Sulfuric Acid Magnetic Nanoparticles: Preparation and Applica­tion in Synthesis of Mono-, Bis-, and Tris-14H-Dibenzo[a,j]xanthen-14-yl­arenes under Solvent-Free Conditions
  作者：Ali Karimi、Zeinab Dalirnasab、Marzie Karimi

  DOI：10.1055/s-0033-1338595

  日期：——

  Novel magnetite-sulfuric acid (Fe3O4 center dot SO3H) magnetic nanoparticles were prepared by the direct reaction of chlorosulfonic acid with magnetite nanoparticles, and characterized by IR spectroscopy, thermogravimetric analysis, X-ray diffraction, and scanning electron microscopy. The catalytic activity of the Fe3O4 center dot SO3H nanoparticles in the reaction of 2-naphthol with aryl mono-, di- and trialdehydes was examined, and these catalysts were shown to exhibit remarkable catalytic performance in the solvent-free synthesis of mono-, bis-, and tris-14H-dibenzo[a,j]xanthen-14-ylarenes. The catalyst retained its activity for several cycles.
• Identification of Diaryl Ether-Based Ligands for Estrogen-Related Receptor α as Potential Antidiabetic Agents
  作者：Raymond J. Patch、Lily L. Searle、Alexander J. Kim、Debyendu De、Xizhen Zhu、Hossein B. Askari、John C. O’Neill、Marta C. Abad、Dionisios Rentzeperis、Jianying Liu、Michael Kemmerer、Ling Lin、Jyotsna Kasturi、John G. Geisler、James M. Lenhard、Mark R. Player、Micheal D. Gaul

  DOI：10.1021/jm101063h

  日期：2011.2.10

  Estrogen-related receptor a (ERR alpha) is an orphan nuclear receptor that has been functionally implicated in the regulation of energy homeostasis. Herein is described the development of diaryl ether based thiazolidenediones, which function as selective ligands against this receptor. Series optimization provided several potent analogues that inhibit the recruitment of a coactivator peptide fragment in in vitro biochemical assays (IC50 < 150 nM) and cellular two-hybrid reporter assays against the ligand binding domain (IC50 = 1-5 mu M). A cocrystal structure of the ligand-binding domain of ERR alpha with lead compound 29 revealed the presence of a covalent interaction between the protein and ligand, which has been shown to be reversible. In diet-induced murine models of obesity and in an overt diabetic rat model, oral administration of 29 normalized insulin and circulating triglyceride levels, improved insulin sensitivity, and was body weight neutral. This provides the first demonstration of functional activities of an ERRa ligand in metabolic animal models.
• Synthesis and computational studies of new metallo-phthalocyanines bearing dibenzoxanthenes and evaluation of their optical properties in solution and solid PMMA/ZnPc/Al nanocomposite films
  作者：Ali Reza KARIMI、Zeinab JAFARZADEH、Meysam SOURINIA、Akbar ZENDEHNAM、Azam KHODADADI、Zeinab DALIRNASAB、Mohammad SOLIMANNEJAD、Peyman ZOLGHARNEIN

  DOI：10.3906/kim-1509-28

  日期：——

  New thermally stable metallo-phthalocyanines bearing dibenzoxanthenes as highly organo-solubilizing aromatic hydrocarbon substituents were successfully prepared by cyclotetramerization of corresponding phthalonitriles with anhydrous metal salts [Zn(CH$_3}$COO)$_2}$ and NiCl$_2}$] in the presence of a catalytic amount of DBU in 2-(dimethylamino) ethanol. All of these phthalocyanines are soluble in some organic solvents such as DMF, DMSO, THF, CH$_2}$Cl$_2}$, and CHCl$_3}$. Then we successfully prepared the poly(methyl methacrylate) (PMMA)/ZnPc/Al nanocomposite films by incorporating Al nanoparticles into a transparent PMMA/ZnPc matrix. The structure and morphology of nanocomposite films were studied using X-ray diffraction and scanning electron microscopy. The optical absorption spectra of PMMA/ZnPc/Al nanocomposite films showed red shifting in the Q-band in the polymeric matrix. The geometrical structure of two phthalocyanines was investigated at the RHF/3-21G* computational level.

  成功合成了新型热稳定金属酞菁化合物，采用二苯并呋喃作为高度有机溶解的芳香烃取代基，通过与无水金属盐（[Zn(CH$_3}$COO)$_2}$ 和 NiCl$_2}$）在2-(二甲基氨基)乙醇中添加催化剂DBU的情况下，循环四聚合得到。这些酞菁均可溶于一些有机溶剂，如DMF、DMSO、THF、CH$_2}$Cl$_2}$和CHCl$_3}$。然后，我们成功地通过将铝纳米颗粒掺入透明的PMMA/ZnPc基体中制备了聚（甲基丙烯酸甲酯）（PMMA）/ZnPc/Al纳米复合膜。利用X射线衍射和扫描电子显微镜对纳米复合膜的结构和形态进行了研究。PMMA/ZnPc/Al纳米复合膜的光学吸收光谱显示出聚合物基体中Q带的红移。两个酞菁的几何结构在RHF/3-21G*计算水平下进行了研究。