4,6-bis{5-(anthracen-9-yl)-2-(hexyloxy)phenyl}-2-methylpyrimidine | 1319659-52-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 4,6-bis{5-(anthracen-9-yl)-2-(hexyloxy)phenyl}-2-methylpyrimidine
• 英文别名: 4,6-Bis(5-anthracen-9-yl-2-hexoxyphenyl)-2-methylpyrimidine；4,6-bis(5-anthracen-9-yl-2-hexoxyphenyl)-2-methylpyrimidine
• CAS: 1319659-52-3
• 化学式: C₅₇H₅₄N₂O₂
• 分子量: 799.068
• InChiKey: MYIBZDPGQBWKSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.8
• 重原子数：
  61
• 可旋转键数：
  16
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  9-蒽硼酸 在 potassium phosphate 、 二(氰基苯)二氯化钯 、 三叔丁基膦 、 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 51.0h， 生成 4,6-bis{5-(anthracen-9-yl)-2-(hexyloxy)phenyl}-2-methylpyrimidine
  参考文献：
  名称：

  Tweezers-like aromatic molecules and their luminescent properties depending on the structures

  摘要：

  Di(hydroxyphenyl)pyrimidine with two anthryl substituents 1a was synthesized and characterized by X-ray crystallography and NMR spectroscopy. The molecule prefers 'U'-shaped conformation supported by intramolecular O-H center dot center dot center dot N hydrogen bonds in the solid state and in solution. The CHCl3-solvated compound binds two CHCl3 molecules between the two parallel anthryl planes. Hexylation of the OH groups of 1a produces 1c whose diarylpyrimidine core contains these aromatic planes with O center dot center dot center dot H-C interaction and helical alignment. Compound 1c shows strong emission from the anthryl groups (410 nm, phi = 0.39), while luminescence is not observed for 1a partly due to quenching via PET (photo-induced electron transfer) process. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.080

文献信息

• Dynamic Properties of Molecular Tweezers with a Bis(2-hydroxyphenyl)pyrimidine Backbone
  作者：Yoshitaka Tsuchido、Yuji Suzaki、Tomohito Ide、Kohtaro Osakada

  DOI：10.1002/chem.201304380

  日期：2014.4.14

  suggested that the complex adopts a stable conformation supported by intramolecular hydrogen bonds among the OH groups and the pyrimidine ring as well as by intermolecular π–π interaction between the anthryl groups and 2,4,7‐trinitrofluorenone. Addition of nBu4NF to a solution of the molecular tweezers or their complexes causes the cleavage of one or two OH⋅⋅⋅N hydrogen bonds, formation of new O⋅⋅⋅HF hydrogen

  4,6-双（2-羟基苯基）-2- alkylpyrimidines与在位置上的两个蒽基或9- ethylnylanthryl取代基对位的OH基团倾向于由两个分子内OH支撑的U形构象⋅⋅⋅在固体N-氢键状态并在CDCl 3溶液中。该化合物在嘧啶基团上具有己基取代基，在羟苯基基团上具有两个9-乙炔基蒽基臂，与2,4,7-三硝基芴酮形成1：1配合物。在298 K时，其缔合常数K a估计为2100  M -1，大于其他分子镊子的缔合常数（K a <1000  M -1）。DFT计算表明，该配合物采用一个稳定的构象，该构象由OH基团和嘧啶环之间的分子内氢键以及蒽基与2,4,7-三硝基芴酮之间的分子间π-π相互作用所支持。在分子镊子或其配合物的溶液中添加n Bu 4 NF会导致一个或两个OH⋅⋅⋅N氢键断裂，形成新的O⋅⋅⋅HF氢键，并改变分子构象。分子镊子的最终结构包含不平行的邻位基团，这些基团不结合客体分子。对具有两个蒽基取代基的4
• Tweezers-like aromatic molecules and their luminescent properties depending on the structures
  作者：Yuji Suzaki、Yoshitaka Tsuchido、Kohtaro Osakada

  DOI：10.1016/j.tetlet.2011.05.080

  日期：2011.7

  Di(hydroxyphenyl)pyrimidine with two anthryl substituents 1a was synthesized and characterized by X-ray crystallography and NMR spectroscopy. The molecule prefers 'U'-shaped conformation supported by intramolecular O-H center dot center dot center dot N hydrogen bonds in the solid state and in solution. The CHCl3-solvated compound binds two CHCl3 molecules between the two parallel anthryl planes. Hexylation of the OH groups of 1a produces 1c whose diarylpyrimidine core contains these aromatic planes with O center dot center dot center dot H-C interaction and helical alignment. Compound 1c shows strong emission from the anthryl groups (410 nm, phi = 0.39), while luminescence is not observed for 1a partly due to quenching via PET (photo-induced electron transfer) process. (C) 2011 Elsevier Ltd. All rights reserved.