9,10-bis(2-formylphenyloxymethyl)anthracene | 135879-38-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-bis(2-formylphenyloxymethyl)anthracene
• 英文别名: 2,2′-((anthracene-9,10-diylbis(methylene)) bis(oxy))dibenzaldehyde；9,10-bis(2-formylphenoxymethyl)anthracene；Benzaldehyde, 2,2'-[9,10-anthracenediylbis(methyleneoxy)]bis-；2-[[10-[(2-formylphenoxy)methyl]anthracen-9-yl]methoxy]benzaldehyde
• CAS: 135879-38-8
• 化学式: C₃₀H₂₂O₄
• 分子量: 446.502
• InChiKey: DGZQUKCYNXCIEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-氨基巴豆腈 、 9,10-bis(2-formylphenyloxymethyl)anthracene 在 溶剂黄146 作用下， 反应 0.17h， 以66%的产率得到4-[2-[[10-[[2-(3,5-Dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)phenoxy]methyl]anthracen-9-yl]methoxy]phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrile
  参考文献：
  名称：

  新型双(1,4-二氢吡啶)基芳烃或杂芳烃的微波辅助多组分合成

  摘要：

  A synthesis of novel bis-1,4-DHPs was reported. Two possible synthetic approaches for these compounds were investigated. In the first approach the monopodal 1,4-DHPs were used as building blocks for the construction of the target molecules via a simple alkylation. In the second strategy the appropriate bis-aldehydes have been synthesized in a first step followed by reaction with four equivalents of 3-aminobut-2-enenitrile using different catalysts under microwave irradiation as well as under conventional heating to give the corresponding bis-1,4-DHPs in good to excellent yield. The oxidative aromatization of some derivatives of the latter compounds into the corresponding bis-2,6-dimethylpyridine-3,5-dicarbonitrile derivatives was achieved using ceric ammonium nitrate (CAN).

  DOI：

  10.3987/com-16-13441
• 作为产物：
  描述：

  蒽 在 aluminum (III) chloride 、 氢溴酸 、 potassium carbonate 、 溶剂黄146 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 9,10-bis(2-formylphenyloxymethyl)anthracene
  参考文献：
  名称：

  短链蒽带卟啉及其内过氧化物

  摘要：

  报道了短链蒽环卟啉及其Zn(II)配合物的合成。关键的合成步骤是二吡咯甲烷和蒽双醛，2,2'-((蒽-9,10-二基双(亚甲基))双(氧基))二苯甲醛之间的[2+2]缩合。暴露于白光后，自敏单线态氧和蒽部分进行 [4+2] 环加成反应，产生相应的内过氧化物。1H NMR 研究表明，内过氧化物很容易在 [D] 氯仿中形成，并在 85 °C 下衰变。X 射线晶体学和吸收光谱用于确认母体带状卟啉和内过氧化物的大环畸变。此外，X 射线晶体学表明，内过氧化物的形成仅发生在蒽部分的外表面。

  DOI：

  10.1002/ejoc.202000283

文献信息

• Synthesis of Strapped, Dimeric, and Trimeric Porphyrins Based on Intramolecular Macrocyclization Reactions
  作者：Atsuhiro Osuka、Fumikazu Kobayashi、Kazuhiro Maruyama

  DOI：10.1246/bcsj.64.1213

  日期：1991.4

  Strapped porphyrins were prepared directly by the acid-catalyzed condensation reaction of 3,3′-diethyl-4,4′-dimethyl-2,2′-dipyrrylmethane and methylenedioxy bridged dialdehydes having a strap linkage longer than 7 atoms. Dimeric and trimeric porphyrins with coplanar and orthogonal (T-shape) geometries were also synthesized in good yields as an application of this method. In the strapped porphyrins, the distortion of porphyrin ring increases systematically on shortening the strap linkage, which is confirmed by their 1H NMR data, red shifted absorption, and fluorescence spectra. In the coplanar dimeric and trimeric porphyrins, the electronic interactions between the porphyrins were distinctly observed, while in the orthogonal “T-shaped” dimers and “H-shaped” trimers, appreciable electronic interactions were not observed.

  通过酸催化的缩合反应，直接制备了由3,3'-二乙基-4,4'-二甲基-2,2'-二吡咯甲烷和含有超过7个原子的带状连接的甲二氧桥二醛反应得到的带状卟啉。该方法的应用还包括以良好产率合成了共平面和正交（T形）几何结构的二聚和三聚卟啉。在带状卟啉中，随着带状连接的缩短，卟啉环的畸变逐渐增加，这一点通过它们的1H NMR数据、红移吸收和荧光光谱得到证实。在共平面二聚和三聚卟啉中，明显观察到卟啉之间的电子相互作用，而在正交的“T形”二聚体和“H形”三聚体中，未观察到明显的电子相互作用。
• Synthesis of novel amide-crownophanes and Schiff base-crownophanes based on<i>p</i>-phenylene, 2,6-naphthalene, and 9,10-anthracene
  作者：Hussni A. Muathen、Nour A. M. Aloweiny、Ahmed H. M. Elwahy

  DOI：10.1002/jhet.129

  日期：2009.7

  The novel macrocyclic diamides , are obtained in 45–66% yields by the reaction of dipotassium salts and with each of 1,4-di(bromomethyl)benzene , 2,6-di(bromomethyl)naphthalene and 9,10-di(bromomethyl)anthracene , repectively, in boiling DMF. On the other hand, the new macrocyclic Schiff bases and are obtained in 44% and 42% yields by heating the appropriate bis-amines , with the corresponding bis-aldehydes

  新型大环二酰胺 ， 通过二钾盐的反应获得45-66％的收率 和 与每个 1,4-二（溴甲基）苯 ， 2,6-二（溴甲基）萘 和 9,10-二（溴甲基）蒽 分别在沸腾的DMF中。另一方面，新的大环席夫碱 和 通过加热适当的双胺可得到44％和42％的收率 ， 与相应的双醛 ， 分别在高稀释条件下于回流乙酸中。J.杂环化​​学。（2009）。
• ——
  作者：S. V. Zaitseva、S. A. Zdanovich、A. S. Semeikin、O. A. Golubchikov

  DOI：10.1023/a:1024978524497

  日期：——

  3,3'-Dibutyl-4,4'-dimethylpyrrolylmethane was reacted with 9,10-bis(2-formylphenyloxymethyl)anthracene to synthesize a capped porphyrin, and its zinc complex was prepared. The coordination properties of the capped zinc porphyrin in extra coordination with N-methylimidazole, imidazole, pyridine, 3,5-dimethylpyrazole, and dimethylformamide in omicron-xylene were studied. A correlation of the stability of the extra complexes and the basicity of the extra ligands was established. A correlation between the stability of the extra complexes and the shifts of their principal electronic absorption bands with respect to those of the zinc porphyrin was found. Deformations of the porphyrin ligand were noted to affect the strengyh of the metal-extra ligand sigma bond. The geometric and energetic characteristics of the fivecoordinate zinc porphyrin were obtained by quantum-chemical calculations. A correlation between the calculated energy of interaction of the central metal atom with the nitrogen atom of the extra ligand and the stability of the extra complexes of the capped Zn porphyrin was revealed.
• Short‐Chained Anthracene Strapped Porphyrins and their Endoperoxides
  作者：Susan Callaghan、Keith J. Flanagan、John E. O'Brien、Mathias O. Senge

  DOI：10.1002/ejoc.202000283

  日期：2020.5.14

  The syntheses of short‐chained anthracene‐strapped porphyrins and their Zn(II)complexes are reported. The key synthetic step is a [2+2] condensation between a dipyrromethane and an anthracene bisaldehyde, 2,2'‐((anthracene‐9,10‐diylbis(methylene))bis(oxy))dibenzaldehyde. Following exposure to white light, self‐sensitized singlet oxygen and the anthracene moieties underwent [4+2] cycloaddition reactions

  报道了短链蒽环卟啉及其Zn(II)配合物的合成。关键的合成步骤是二吡咯甲烷和蒽双醛，2,2'-((蒽-9,10-二基双(亚甲基))双(氧基))二苯甲醛之间的[2+2]缩合。暴露于白光后，自敏单线态氧和蒽部分进行 [4+2] 环加成反应，产生相应的内过氧化物。1H NMR 研究表明，内过氧化物很容易在 [D] 氯仿中形成，并在 85 °C 下衰变。X 射线晶体学和吸收光谱用于确认母体带状卟啉和内过氧化物的大环畸变。此外，X 射线晶体学表明，内过氧化物的形成仅发生在蒽部分的外表面。
• Microwave Assisted Multi-Component Synthesis of Novel Bis(1,4-dihydropyridines) Based Arenes or Heteroarenes
  作者：Ahmed H. M. Elwahy、Ismail A. Abdelhamid、Sherif M. H. Sanad、Refaie M. Kassab

  DOI：10.3987/com-16-13441

  日期：——

  A synthesis of novel bis-1,4-DHPs was reported. Two possible synthetic approaches for these compounds were investigated. In the first approach the monopodal 1,4-DHPs were used as building blocks for the construction of the target molecules via a simple alkylation. In the second strategy the appropriate bis-aldehydes have been synthesized in a first step followed by reaction with four equivalents of 3-aminobut-2-enenitrile using different catalysts under microwave irradiation as well as under conventional heating to give the corresponding bis-1,4-DHPs in good to excellent yield. The oxidative aromatization of some derivatives of the latter compounds into the corresponding bis-2,6-dimethylpyridine-3,5-dicarbonitrile derivatives was achieved using ceric ammonium nitrate (CAN).