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。
• 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.
• 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.