tetrapropoxycalix[4]arene tetracarboxylic acid chloride | 208403-70-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tetrapropoxycalix[4]arene tetracarboxylic acid chloride
• 英文别名: 25,26,27,28-tetra-n-propoxycalix[4]arene-5,11,17,23-tetracarbonyl chloride；25,26,27,28-Tetrapropoxypentacyclo[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-5,11,17,23-tetracarbonyl chloride
• CAS: 208403-70-7
• 化学式: C₄₄H₄₄Cl₄O₈
• 分子量: 842.641
• InChiKey: ILUAADCBJYGDAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  56
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tetrapropoxycalix[4]arene tetracarboxylic acid chloride 在 lithium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 10.0h， 生成 25,26,27,28-tetra-n-propoxycalix[4]arene-5,11,17,23-tetrakis(carbonyl-N-L-alanine)
  参考文献：
  名称：

  上缘具有L-丙氨酸单元的手性锥杯[4]芳烃的合成与结构

  摘要：

  开发了合成路线以在锥形构象中封闭的杯[4]芳烃的上缘连接L-丙氨酸甲酯或L-丙氨酰-L-丙氨酸甲酯。获得了几个含有大环的四（3 和 6）和双官能化（11 和 12）氨基酸。这些化合物与肼反应生成相应的酰肼衍生物 4、13 和 14，而 3 用 LiOH 水解生成四酸 5，其锂盐在中性 pH 值下可溶于水。通过单维和二维 1H NMR 实验研究了所有含有杯 [4] 芳烃的氨基酸的结构特性。双官能化受体11的X射线晶体结构在固态下显示出三种不同的构象，没有一种具有链内氢键。

  DOI：

  10.1002/(sici)1099-0690(199805)1998:5<897::aid-ejoc897>3.0.co;2-k
• 作为产物：
  描述：

  tetra-O-propoxy-p-carboxylatocalix[4]arene 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 tetrapropoxycalix[4]arene tetracarboxylic acid chloride
  参考文献：
  名称：

  上缘具有L-丙氨酸单元的手性锥杯[4]芳烃的合成与结构

  摘要：

  开发了合成路线以在锥形构象中封闭的杯[4]芳烃的上缘连接L-丙氨酸甲酯或L-丙氨酰-L-丙氨酸甲酯。获得了几个含有大环的四（3 和 6）和双官能化（11 和 12）氨基酸。这些化合物与肼反应生成相应的酰肼衍生物 4、13 和 14，而 3 用 LiOH 水解生成四酸 5，其锂盐在中性 pH 值下可溶于水。通过单维和二维 1H NMR 实验研究了所有含有杯 [4] 芳烃的氨基酸的结构特性。双官能化受体11的X射线晶体结构在固态下显示出三种不同的构象，没有一种具有链内氢键。

  DOI：

  10.1002/(sici)1099-0690(199805)1998:5<897::aid-ejoc897>3.0.co;2-k

文献信息

• Calix[4]arenes with perfluorinated alcoholic functions at the upper rim: a new class of neutral anion receptors
  作者：N. Pelizzi、A. Casnati、R. Ungaro

  DOI：10.1039/a806837b

  日期：——

  Two or four perfluorinated alcoholic functions were successfully introduced at the upper rim of calix[4]arenes, affording a new type of neutral receptor for anion recognition; preliminary binding studies indicate that the difunctionalized receptors 3a and 3b are selective for Y-shaped carboxylate ions over spherical anions which are, on the contrary, more efficiently bound by the tetraalcohol 6.

  在上缘成功引入两个或四个全氟代醇功能团，得到了一种新型中性阴离子识别受体；初步结合研究表明，双功能化受体3a和3b对Y形羧酸盐离子具有选择性，而与此相反，四醇6则更有效地结合球形阴离子。
• Transglutaminase surface recognition by peptidocalix[4]arene diversomers
  作者：Simona Francese、Anna Cozzolino、Ivana Caputo、Carla Esposito、Marco Martino、Carmine Gaeta、Francesco Troisi、Placido Neri

  DOI：10.1016/j.tetlet.2005.01.078

  日期：2005.3

  A series of N-linked tetrakis(tetrapeptido)calix[4]arene diversomers, 3A-P, has been synthesized by Coupling of a cone calix[4]arene tetracarboxylic acid chloride with tetrapeptides 1A-P obtained in a parallel fashion. The inhibition activity of 3A-P towards tissue and microbial transglutaminase was evaluated by in vitro assays with a labeled substrate. Kinetic analysis using one of the most active derivatives (3A) showed a noncompetitive inhibition with respect to the amino acceptor Substrate and an uncompetitive inhibition with respect to amino donor substrate. Experimental results are in accordance with ail inhibition due to a protein specific surface recognition on a region noncomprising the enzyme active site. (C) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and Structure of ChiralCone Calix[4]arenes Functionalized at the Upper Rim with L-Alanine Units
  作者：Francesco Sansone、Silvia Barboso、Alessandro Casnati、Massimo Fabbi、Andrea Pochini、Franco Ugozzoli、Rocco Ungaro

  DOI：10.1002/(sici)1099-0690(199805)1998:5<897::aid-ejoc897>3.0.co;2-k

  日期：1998.5

  link L-alanine methyl ester or L-alanyl-L-alanine methyl ester at the upper rim of calix[4]arenes blocked in the cone conformation. Several tetra- (3 and 6) and difunctionalized (11 and 12) amino acids containing macrocycles were obtained. Reaction of these compounds with hydrazine gave the corresponding hydrazido derivatives 4, 13, and 14, while the hydrolysis of 3 with LiOH produced the tetraacid

  开发了合成路线以在锥形构象中封闭的杯[4]芳烃的上缘连接L-丙氨酸甲酯或L-丙氨酰-L-丙氨酸甲酯。获得了几个含有大环的四（3 和 6）和双官能化（11 和 12）氨基酸。这些化合物与肼反应生成相应的酰肼衍生物 4、13 和 14，而 3 用 LiOH 水解生成四酸 5，其锂盐在中性 pH 值下可溶于水。通过单维和二维 1H NMR 实验研究了所有含有杯 [4] 芳烃的氨基酸的结构特性。双官能化受体11的X射线晶体结构在固态下显示出三种不同的构象，没有一种具有链内氢键。
• Molecular Acrobatics:  Self-Assembly of Calixarene-Porphyrin Cages
  作者：Laura Baldini、Pablo Ballester、Alessandro Casnati、Rosa M. Gomila、Christopher A. Hunter、Francesco Sansone、Rocco Ungaro

  DOI：10.1021/ja036758a

  日期：2003.11.1

  Calix[4]arenes equipped with two and four zinc porphyrins have been prepared, and they show remarkable flexibility in their self-assembly properties with the bidentate ligand DABCO. The calix-bisporphyrin forms a 2:2 complex with DABCO, generating a large cavity that has the potential to act as a supramolecular host. The calix-tetraporphyrin, on the other hand, forms four different complexes with DABCO depending on the stoichiometry and concentration. During the course of a titration, all four complexes are populated, leading to large conformational changes and the formation of both intramolecular and intermolecular calix-tetraporphyrin-DABCO sandwich complexes. The system was fully characterized using a combination of UV-visible and H-1 NMR spectroscopy to identify the complexes. At a calix-tetraporphyrin: DABCO ratio of 2:4, the major species is dimeric cage assembly that features a large internal cavity for guest complexation.