5,11,17,23-tetra-tert-butyl-25-hydroxy-26,27-dipropoxy-28-(2-pyridylmethoxy)calix<4>arene | 131375-76-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,11,17,23-tetra-tert-butyl-25-hydroxy-26,27-dipropoxy-28-(2-pyridylmethoxy)calix<4>arene
• 英文别名: 5,11,17,23-tetra-tert-butyl-25-hydroxy-26,27-dipropoxy-28-(2-pyridylmethoxy)calix[4]arene；5,11,17,23-tetratert-butyl-26,27-dipropoxy-28-(pyridin-2-ylmethoxy)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3(28),4,6,9,11,13(27),15,17,19(26),21(25),22-dodecaen-25-ol
• CAS: 131375-76-3；131375-77-4；131375-78-5
• 化学式: C₅₆H₇₃NO₄
• 分子量: 824.2
• InChiKey: AHZJXQDWBLUFNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.81
• 重原子数：
  61.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  60.81
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-氯甲基吡啶盐酸盐 在 barium dihydroxide 、 sodium hydride 、 barium(II) oxide 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 28.0h， 生成 5,11,17,23-tetra-tert-butyl-25-hydroxy-26,27-dipropoxy-28-(2-pyridylmethoxy)calix<4>arene
  参考文献：
  名称：

  下缘不对称取代的手性杯[4]芳烃的合成及光学拆分

  摘要：

  锥形、不对称取代的杯[4]芳烃通过逐步O-烷基化方法合成，并通过HPLC方法进行光学解析。这是成功光学拆分具有环源手性的杯[4]芳烃的第一个例子。

  DOI：

  10.1246/cl.1990.1901

文献信息

• Syntheses and optical resolution of calix[4]arenes with molecular asymmetry. Systematic classification of all possible chiral isomers derivable from calix[4]arene
  作者：Koji Iwamoto、Hiroyasu Shimizu、Koji Araki、Seiji Shinkai

  DOI：10.1021/ja00063a020

  日期：1993.5

  All possible chiral isomers that can be derived from calix[4]arene by modification of the OH groups were systematically classified. Molecular asymmetry can be generated not only by different substituents but also by conformational isomerism. The numbers of chiral isomers are 24 for tetra-O-substituted calix[4]arenes, 10 for tri-O-substituted calix[4]arenes, 3 for di-O-substituted calix[4]arenes, and 0 for mono-O-substituted calix[4]arenes. This implies that calix[4]arene is a useful building block for the design of novel asymmetric ring structures. In order to demonstrate asymmetry in these chiral calix[4]arenes, we synthesized several tetra-, tri-, and di-O-substituted calix[4]arenes by using the metal template method, the stepwise synthesis method, the protection-deprotection method, etc., which were developed in efforts directed toward regioselective O-alkylation and control of conformational isomerism in calix[4]arenes. Finally, we succeeded in complete optical resolution of chiral calix[4]arenes by an HPLC method using a chiral-packed column or by the formation of diastereomers with the (-)-menthoxyacetyl group. This article thus contains all of the molecular design concepts, syntheses, and optical resolutions of chiral calix[4]arenes.
• Iwamoto Koji, Shimizu Hiroyasu, Araki Koji, Shinkai Seiji, J. Amer. Chem. Soc., 115 (1993) N 10, S 3997-4006
  作者：Iwamoto Koji, Shimizu Hiroyasu, Araki Koji, Shinkai Seiji

  DOI：——

  日期：——