2,6-diformyl-4-phenylphenol | 220339-82-2

• 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: 2,6-diformyl-4-phenylphenol
• 英文别名: 4-Hydroxy[1,1a(2)-biphenyl]-3,5-dicarboxaldehyde；2-hydroxy-5-phenylbenzene-1,3-dicarbaldehyde
• CAS: 220339-82-2
• 化学式: C₁₄H₁₀O₃
• 分子量: 226.232
• InChiKey: CPUVUNMGNPADIO-UHFFFAOYSA-N

物化性质

• 沸点：
  352.3±42.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-diformyl-4-phenylphenol 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以50%的产率得到4-hydroxy-5-((hydroxyimino)methyl)-[1,1'-biphenyl]-3-carbaldehyde
  参考文献：
  名称：

  Ratiometric pH responsive fluorescent probes operative on ESIPT

  摘要：

  A series of C-8'-oxime-appended spirobenzopyrans 4a-4d were synthesized and developed as fluorescent pH ratiometric probes operative in HEPES/ACN (8:2, v/v) buffer solutions. Acidochromic conversion of spirobenzopyran to merocyanine open form can facilitate the subsequent enol-keto tautomerization giving dual emissive peaks via the excited state intramolecular proton transfer (ESIPT) mechanism. The pH titrations of 4a show a 68-fold increase in ratiometric intensities ratio (I-645 nm/I-522 (nm)) when the pH was switched from 8.0 to 4.0 with a pK(a) value of 5.90. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.023
• 作为产物：
  描述：

  4-溴苯酚 在 potassium fluoride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三氟乙酸 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 40.0h， 生成 2,6-diformyl-4-phenylphenol
  参考文献：
  名称：

  对芳基取代的水杨二醛的合成

  摘要：

  对位取代的水杨二醛是用于多孔有机笼、荧光染料、螺苯并吡喃、高氧杂杯芳烃、双核金属配合物、大环化合物和穴状配体的通用分子构件。迄今为止，尚未报道合成对芳基取代的水杨二醛的方法，这将拓宽上述主题的范围，特别是在传感器和染料领域，因为芳香π系统可以扩大和吸收或荧光事件可以通过各种取代基进行微调。在此，报道了具有吸电子和供电子芳族单元的对芳基取代的水杨二醛的两种合成路线。

  DOI：

  10.1002/ejoc.201500228

文献信息

• Ru-Based Complexes as Heterogeneous Potential Catalysts for the Amidation of Aldehydes and Nitriles in Neat Water
  作者：Wael Abdelgayed Ahmed Arafa

  DOI：10.1246/bcsj.20200071

  日期：2020.9.15

  Five novel heterogeneous mononuclear complex-anchored Ru(III) have been efficiently sono-synthesized and characterized by utilizing several analytical techniques. The assembled complexes could be utilized as effective, robust and recyclable (up to eight consecutive runs) catalysts for one-pot transformation of a vast array of nitriles and aldehydes to primary amides in H2O under aerobic conditions. Moreover, some unreported di- and tetra-amide derivatives were obtained also under the optimal conditions. The results of ICP/OES analysis demonstrated that there is no detected leaching of the recycled catalyst, which suggests the real heterogeneity of the present protocol. The present Ru-complexes exhibited superiority compared to other reported catalysts for amide preparation in terms of low catalyst load, short reaction time, low operating temperature, no hazardous additives required, and high values of TON (990) and TOF (1980 h−1).

  摘要 利用多种分析技术高效地超声合成了五种新型异质单核络合物锚定 Ru（III），并对其进行了表征。在有氧条件下，这些组装好的配合物可作为有效、稳定和可循环（最多可连续运行八次）的催化剂，用于在 H2O 中将大量腈类和醛类化合物一锅转化为伯胺。此外，在最佳条件下还获得了一些未报道过的二酰胺和四酰胺衍生物。ICP/OES 分析结果表明，没有检测到回收催化剂的沥滤现象，这表明本方案具有真正的异质性。与其他已报道的酰胺制备催化剂相比，本发明的 Ru 复合物具有催化剂载量低、反应时间短、操作温度低、无需有害添加剂、TON 值（990）和 TOF 值（1980 h-1）高等优点。
• New synthetic route to homooxacalix[n]arenes via reductive coupling of diformylphenols
  作者：Naoki Komatsu

  DOI：10.1016/s0040-4039(00)02336-4

  日期：2001.2

  homocoupling of 4-substituted-2,6-diformylphenols with Et3SiH in the presence of Me3SiOTf gave homooxacalix[n]arenes (1n·R, n=3, 4) in moderate yields. Heterocoupling reaction of 4-substituted-2,6-diformylphenols with tris(trimethylsilyl) ether of 4-substituted-2,6-bis(hydroxymethyl)phenols afforded homooxacalix[n]arenes (23·R1·R2·Rm and 24·R1·R2·R1·Rm, m=1, 2) with different substituents in a one-pot fashion

  在Me 3 SiOTf存在下，4-取代的2,6-二甲酰基苯酚与Et 3 SiH的还原均偶联反应以中等收率得到了高恶唑烷[ n ]芳烃（1 n ·R，n = 3，4）。4-取代的2,6-二甲酰基苯酚与4-取代的2,6-双（羟甲基）苯酚的三（三甲基甲硅烷基）醚的异质偶联反应得到高氧杂芳基[ n ]芳烃（2 3 ·R 1 ·R 2 ·R m和2 4 ·R 1 ·R 2 ·R 1 ·R m，m= 1，2）以一锅的方式带有不同的取代基。
• Awkwardly-Shaped Dimers, Capsules and Tetramers: Molecular and Supramolecular Motifs in C5-Arylated Chiral Calixsalens
  作者：Małgorzata Petryk、Agnieszka Janiak、Leonard J. Barbour、Marcin Kwit

  DOI：10.1002/ejoc.201800314

  日期：2018.4.30

  Novel C‐5‐functionalized calixsalens show substituent‐driven self‐association that can lead to the formation of supramolecules in the solid state.

  新型的C-5功能化杯盖草素显示出取代基驱动的自缔合，可导致固态超分子的形成。
• AROMATIC POLYIMINE, PROCESS FOR PRODUCING THE SAME, AROMATIC POLYIMINE OLIGOMER USED FOR PRODUCING SAID POLYIMINE, AND PROCESS FOR PRODUCING SAID OLIGOMER
  申请人：ARAKAWA KAGAKU KOGYO KABUSHIKI KAISHA

  公开号：EP0662486A1

  公开（公告）日：1995-07-12

  An aromatic polyimine oligomer comprising repeating units composed of an aromatic dialdehyde having a phenolic hydroxyl group and an aromatic diamine and having a number-average degree of polymerization of 2 to 20, and a process for producing the same. An aromatic polyimine and a process for producing the same by thermally dehydrating the oligomer.

  一种芳香族聚酰亚胺低聚物，其重复单元由具有酚羟基的芳香族二醛和芳香族二胺组成，平均聚合度为 2 至 20。一种芳香族聚酰亚胺和一种通过对低聚物进行热脱水生产该聚酰亚胺的工艺。
• A tris-phenylphenol N8O3 Schiff-base cryptand: structural characterization and fluorescence titration for lanthanide coordination
  作者：Shu-Yan Yu、Biao Wu、Xiao-Juan Yang、Wen-Jian Zhang、Xintao Wu、Takahiro Kusukawa

  DOI：10.1002/(sici)1099-1395(199812)11:12<903::aid-poc80>3.0.co;2-m

  日期：1998.12

  Lanthanide [lanthanum(III), 2; europium(III), 3; and gadolinium(III), 4] cryptates of a tris phenylphenol N8O3 Schiff-base cryptand (H3L) were synthesized by transmetallation with [Na(H3L)]ClO4.3H(2)O (1) and characterized by spectroscopic and crystal structure analyses. Both 3 and 4 are isomophous and isostructural. The complexes crystallize in the triclinic space group P-1 with cell parameters for 3 of a = 14.9833(2), b = 15.42670(10), c = 16.3770(3) Angstrom, alpha = 75.37606(10), beta = 68.2640(10), gamma = 77.0540(10)degrees and Z = 2 and for 4 of a = 14.9976(3), b = 15.4417(3), c = 16.35350(10) Angstrom, alpha = 75.3980(10), beta = 68.3180(10), gamma = 76.8790(10)degrees and Z = 2. The structures reveal that one lanthanide ion is unsymmetrically encapsulated in the cryptand cavity with a second ligand (solvent DMF). Solution NMR and solid structural studies demonstrated that there are intracavity and intermolecular proton transfer processes during lanthanide complexation towards the cryptand. A fluorimetric titration in acetonitrile for Eu(III) ion to 1 afforded a novel fluorescence intensity (I-F)-equivalents of Eu(III) ion (x) plot signaling a quenching (0 < x < 0.2)-enhancement (0.2 < x < 1) change with formation of the kinetically stable 1:1 cryptate. An energy-transfer mechanism is discussed. (C) 1998 John Wiley & Sons, Ltd.