5,11,17,23-tetrakis(carboxymethyl)calix[4]arene-25,26,27,28-tetrol | 155562-05-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5,11,17,23-tetrakis(carboxymethyl)calix[4]arene-25,26,27,28-tetrol
• 英文别名: 2-[11,17,23-Tris(carboxymethyl)-25,26,27,28-tetrahydroxy-5-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-dodecaenyl]acetic acid
• CAS: 155562-05-3
• 化学式: C₃₆H₃₂O₁₂
• 分子量: 656.643
• InChiKey: IEOIGIQLKJHJBW-UHFFFAOYSA-N

物化性质

• 沸点：
  931.6±65.0 °C(Predicted)
• 密度：
  1.507±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  48
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  230
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetrakis(carboxymethyl)calix[4]arene-25,26,27,28-tetrol 在 氢氧化钾 、 乙酸酐 、 potassium carbonate 、 sodium iodide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 84.0h， 生成 bisanhydride of 5,11,17,23-tetrakis(carboxymethyl)-25,26,27,28-tetrakis(benzyloxy)calix[4]arene
  参考文献：
  名称：

  Synthesis and Reactions of Calix[4]arene Bisanhydrides¹

  摘要：

  The tetrabenzyl ether, tetra-p-bromobenzenesulfonate, and tetra-p-methylbenzenesulfonate of p-carboxymethylcalix[4]arene in the 1,3-alternate conformation have been converted to the corresponding bisanhydrides. Reactions of the bisanhydrides with alcohols or amines afford calix[4]arenes carrying two carboxymethyl and two carboalkoxymethyl or two amidomethyl groups on the upper rim positions. The substitution pattern that is established confers molecular chirality on the calixarenes.

  DOI：

  10.1021/jo9822636
• 作为产物：
  描述：

  5,11,17,23-tetracyanomethyl-25,26,27,28-tetra(benzyloxy)calix[4]arene 在 硫酸 、 水 、 溶剂黄146 作用下， 反应 6.0h， 生成 5,11,17,23-tetrakis(carboxymethyl)calix[4]arene-25,26,27,28-tetrol
  参考文献：
  名称：

  Upper Rim Substitution of Calixarenes: Carboxylic Acids

  摘要：

  单取代（5a）、双取代（4a 和 4b）以及四取代（1a）对位氰基甲基卡利克斯[4]芳烃和双（氰基甲基）卡利克斯[6]芳烃（6a）经过酸和碱诱导的水解反应，转化为相应的对位羧基甲基卡利克斯[4]芳烃（5b、4c、4d、2a 和 6b），而这些产物又进一步转化为甲酯（5c、4e、4f、2b）和乙酯（5d、4g、2c）。然而，立体障碍化合物 7 和 8 及其对应的单体 10 和 11 中的氰基甲基在严格条件下对此反应表现出惰性，未能发生水解。甲酯 2b 可转化为 1,3-二苄基醚（3b）、1,3-二苄酸酯（3c）、四苄基醚（3a）和四苄酸酯（3d）。

  DOI：

  10.1055/s-1997-1359

文献信息

• Design and synthesis of new polyphosphorylated upper-rim modified calix[4]arenes as potential and selective chelating agents of uranyl ion
  作者：Evelyne Migianu-Griffoni、Cyrille Mbemba、Ramon Burgada、Delphine Lecerclé、Frédéric Taran、Marc Lecouvey

  DOI：10.1016/j.tet.2008.11.076

  日期：2009.2

  New upper-rim polyphosphorylated calix[4]arenes were designed for decorporation of uranium in case of nuclear contamination. A ligand system containing four preorganized 1-hydroxymethylene-1,1-bisphosphonic acid moieties anchored onto a calix[4]arene platform has been developed. Three calix[4]arene-bisphosphonates were efficiently prepared in multi-step syntheses with a variable carbon chain length

  设计了一种新的上边缘多磷酸化杯[4]芳烃，用于在核污染的情况下使铀脱附。已经开发了一种配体系统，该系统包含锚定在杯[4]芳烃平台上的四个预组织的1-羟基亚甲基-1,1-双膦酸部分。通过多步合成有效地制备了三种杯[4]芳烃-双膦酸酯，双膦酸酯和杯[4]芳烃之间的碳链长度可变。确定了对铀酰离子的亲和常数，并将其与双（HEDP）和三（HEDP）膦酸酯（被称为铀酰的有效配体）的亲和常数进行了比较。
• Calixpenams: synthesis, characterization, and biological evaluation of penicillins V and X clustered by calixarene scaffold
  作者：Fazel NASUHI PUR、Karim AKBARI DILMAGHANI

  DOI：10.3906/kim-1307-32

  日期：——

  Four 6-aminopenicillanic acid moieties were grafted at either rim of calix[4]arene, giving 2 novel generations of penicillin, which were named calixpenam. Antibiotic tests showed that they have amplified activity with respect to the corresponding penams against 3 gram-positive nonpenicillinase-producing strains of Streptococcus.

  在卡利克[4]炔的两端接枝了四个 6-氨基青霉烷酸分子，从而产生了两代新型青霉素，并将其命名为卡利克青霉烷。抗生素测试表明，与相应的青霉烷胺相比，它们对 3 种革兰氏阳性不产青霉素酶链球菌菌株的活性有所提高。
• Synthesis and anti-HIV evaluation of water-soluble calixarene-based bithiazolyl podands
  作者：Maxime Mourer、Nicolas Psychogios、Géraldine Laumond、Anne-Marie Aubertin、Jean-Bernard Regnouf-de-Vains

  DOI：10.1016/j.bmc.2009.11.016

  日期：2010.1

  Nine anionic water-soluble calix[4] arene species, incorporating sulfonate, carboxylate or phosphonate groups, six of them incorporating two 2,2'-bithiazole subunits in alternate position at the lower rim, have been synthesised and evaluated as anti-HIV agents on various HIV strains and cells of the lymphocytic lineage (HIV-1 III B/MT4, HIV-1 LAI/CEM-SS, HIV-1 Bal/PBMC), using AZT as reference compound. A toxicity was detected for a minority of compounds on PBMC whereas for the others no cellular toxicity was measured at concentrations up to 100 mu M. Most of the compounds have an antiviral activity in a 10-50 mu M range, and one of them, sulfonylated, displays its activity, whatever the tropism of the virus, at a micromolar concentration. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis and Reactions of Calix[4]arene Bisanhydrides¹
  作者：Shiv Kumar Sharma、C. David Gutsche

  DOI：10.1021/jo9822636

  日期：1999.5.1

  The tetrabenzyl ether, tetra-p-bromobenzenesulfonate, and tetra-p-methylbenzenesulfonate of p-carboxymethylcalix[4]arene in the 1,3-alternate conformation have been converted to the corresponding bisanhydrides. Reactions of the bisanhydrides with alcohols or amines afford calix[4]arenes carrying two carboxymethyl and two carboalkoxymethyl or two amidomethyl groups on the upper rim positions. The substitution pattern that is established confers molecular chirality on the calixarenes.
• Upper Rim Substitution of Calixarenes: Carboxylic Acids
  作者：Shiv Kumar Sharma、Suseela Kanamathareddy、C. David Gutsche

  DOI：10.1055/s-1997-1359

  日期：1997.11

  The mono- (5a), bis- (4a and 4b), and tetrakis (1a)-p-cyanomethylcalix[4]arenes as well as the bis(cyanomethyl)calix[6]arene (6a) have been transformed both by acid and base induced hydrolysis to the corresponding p-carboxymethylcalix[4]arenes 5b, 4c, 4d, 2a, and 6b which, in turn, were converted to the methyl (5c, 4e, 4f, 2b) and ethyl (5d, 4g, 2c) esters. The cyanomethyl groups in the sterically hindered compounds 7 and 8 and their corresponding monomers 10 and 11, however, were inert to hydrolysis, even under strenuous conditions. The methyl ester 2b can be converted to the 1,3-dibenzyl ether (3b) and the 1,3-dibenzoate (3c) as well as the tetrabenzyl ether (3a) and tetrabenzoate (3d).

  单取代（5a）、双取代（4a 和 4b）以及四取代（1a）对位氰基甲基卡利克斯[4]芳烃和双（氰基甲基）卡利克斯[6]芳烃（6a）经过酸和碱诱导的水解反应，转化为相应的对位羧基甲基卡利克斯[4]芳烃（5b、4c、4d、2a 和 6b），而这些产物又进一步转化为甲酯（5c、4e、4f、2b）和乙酯（5d、4g、2c）。然而，立体障碍化合物 7 和 8 及其对应的单体 10 和 11 中的氰基甲基在严格条件下对此反应表现出惰性，未能发生水解。甲酯 2b 可转化为 1,3-二苄基醚（3b）、1,3-二苄酸酯（3c）、四苄基醚（3a）和四苄酸酯（3d）。