dimethyl 4,4′-(25,26,27,28-tetrapropoxycalix[4]-arene-5,17-diyl)bis(6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate) | 1610712-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: dimethyl 4,4′-(25,26,27,28-tetrapropoxycalix[4]-arene-5,17-diyl)bis(6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate)
• CAS: 1610712-84-9
• 化学式: C₅₄H₆₄N₄O₈S₂
• 分子量: 961.256
• InChiKey: ZFFAZVSICGFSHF-UHFFFAOYSA-N

物化性质

• 熔点：
  234-238 °C
• 沸点：
  985.3±75.0 °C(predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.45
• 重原子数：
  68.0
• 可旋转键数：
  16.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  137.64
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  乙酰乙酸甲酯 、 硫脲 、 5,17-diformyl-25,26,27,28-tetra-(1-propoxy)calix[4]arene 以 溶剂黄146 为溶剂， 反应 4.0h， 以85%的产率得到dimethyl 4,4′-(25,26,27,28-tetrapropoxycalix[4]-arene-5,17-diyl)bis(6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate)
  参考文献：
  名称：

  Synthesis and structure of [2-oxo(thioxo)tetrahydropyrimidin-4-yl]calix[4]arenes

  摘要：

  Cone-shaped di- and tetrapropoxycalix[4]arenes functionalized at the upper rim with one or two 2-oxo(thioxo)tetrahydropyrimidine residues were synthesized by the Biginelli reaction of formylcalixarenes with urea (thiourea) and methyl acetoacetate. The steric structure of the products was studied by NMR and X-ray diffraction. The Biginelli reaction with dipropoxyformylcalixarene was diastereoselective, and it quantitatively produced the corresponding meso form. Tetrapropoxydiformylcalixarenes under analogous conditions gave rise to equimolar mixtures of racemic and meso compounds. The macrocyclic skeleton of the synthesized pyrimidine-containing calixarenes in crystal and in solution has a flattened cone conformation. (5-Methoxycarbonyl-2-oxotetrahydropyrimidin-4-yl)calixarene molecules in crystal undergo self-organization to form infinite chains via repeated inclusion of the methoxy group into the cavity of the neighboring macrocycle. Selforganization of bis(5-methoxycarbonyl-2-oxotetrahydropyrimidin-4-yl)calixarene with formation of analogous chains involves intermolecular hydrogen bonding NH ... O=C.

  DOI：

  10.1134/s1070428014040228