25,26,27,28-tetrabutoxy-5,11,17,23-tetrakis(cyclohepta-2,4,6-trienyl)calix[4]arene | 188691-69-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 25,26,27,28-tetrabutoxy-5,11,17,23-tetrakis(cyclohepta-2,4,6-trienyl)calix[4]arene
• 英文别名: 25,26,27,28-Tetrabutoxy-5,11,17,23-tetra(cyclohepta-2,4,6-trien-1-yl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene
• CAS: 188691-69-2
• 化学式: C₇₂H₈₀O₄
• 分子量: 1009.42
• InChiKey: YPBFDYBPFWMYFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.4
• 重原子数：
  76
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  25,26,27,28-tetrabutoxy-5,11,17,23-tetrakis(cyclohepta-2,4,6-trienyl)calix[4]arene 在 trityl tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到
  参考文献：
  名称：

  1,3,5-Cycloheptatrienyl derivatives of calix[4]- and calix[6]arenes and their corresponding tropylium salts

  摘要：

  Tetrakis-(p-cycloheptatrienyl-7)calix[4]arene and hexakis-(p-cycloheptatrienyl-7)calix[6]arene have been synthesized. The oxidation affords calixarenes with four or six positively charged substituents at the upper rim. Whereas the cycloheptatrienyl substituent has little influence on the conformational flexibility of the macrocycle, the tropylium substituents reduce the interconversional hauler. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00007-5
• 作为产物：
  描述：

  7-methoxy-1,3,5-cycloheptatriene 在 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 paraffin 为溶剂， 反应 94.0h， 生成 25,26,27,28-tetrabutoxy-5,11,17,23-tetrakis(cyclohepta-2,4,6-trienyl)calix[4]arene
  参考文献：
  名称：

  1,3,5-Cycloheptatrienyl derivatives of calix[4]- and calix[6]arenes and their corresponding tropylium salts

  摘要：

  Tetrakis-(p-cycloheptatrienyl-7)calix[4]arene and hexakis-(p-cycloheptatrienyl-7)calix[6]arene have been synthesized. The oxidation affords calixarenes with four or six positively charged substituents at the upper rim. Whereas the cycloheptatrienyl substituent has little influence on the conformational flexibility of the macrocycle, the tropylium substituents reduce the interconversional hauler. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00007-5

文献信息

• Inclusion of Organic Cations by Calix[4]arenes Bearing Cyclohepta-2,4,6-trienyl Substituents
  作者：Marzena Orda-Zgadzaj、Volker Wendel、Matthias Fehlinger、Burkhard Ziemer、Werner Abraham

  DOI：10.1002/1099-0690(200104)2001:8<1549::aid-ejoc1549>3.0.co;2-x

  日期：2001.4

  Only very weak complexation of organic cations such as ammonium and iminium ions by simple calix[4]arenes has been reported to date. Newly designed calix[4]arenes, substituted with a different number of 1,3,5-cycloheptatrien-7-yl functions at the upper rim. can engender an improvement in the inclusion capability, due to an enlargement of the Jr-basic wall of the host cavity. The complexation capability of these calix[4]arenes for organic cations is studied in this paper, For the first time, aryl tropylium salts have been used as cationic guests in addition to ammonium and iminium salts. Three structural types of hosts can be distinguished, all of which exhibit remarkably different inclusion abilities towards the organic cations, Flexible hosts with an OK-unmodified lower rim undergoing ring inversion form complexes of modest stability, provided that the host lacks bulky tert-butyl substituents at the upper rim. Tetra-O-alkylated derivatives, which are assumed to exhibit a flexible cone conformation, do not bind organic cations. Among the calix[4]arenes bearing cycloheptatrienyl groups, the complexation requirements are best matched by hosts with four cycloheptatrienyl groups on the upper rim and two alkyl groups on the lower rim; these compounds are assumed to possess a more rigid cone conformation, due to intramolecular hydrogen bonds. The tropylium component of phenyl tropylium ions penetrates inside the pi -basic cavity of the host. The absorption coefficient of the longest wavelength absorption band of these guests in the visible region is drastically lessened upon inclusion.