25,26,27,28-tetradecyloxycalix<4>arene | 160413-54-7

• 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-tetradecyloxycalix<4>arene
• 英文别名: 25,26,27,28-tetradecyloxycalix[4]arene；25,26,27,28-Tetrakis-decoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene
• CAS: 160413-54-7；561029-60-5
• 化学式: C₆₈H₁₀₄O₄
• 分子量: 985.571
• InChiKey: LEBLSIWQJQRWQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  25.6
• 重原子数：
  72
• 可旋转键数：
  40
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 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-tetradecyloxycalix<4>arene 在 硝酸 、 1-羟基苯并三唑 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 tin(ll) chloride 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 2-(5-methyl-2,4-dioxopyrimidin-1-yl)-N-[25,26,27,28-tetrakis-decoxy-11-[[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]amino]-5-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-dodecaenyl]acetamide
  参考文献：
  名称：

  Synthesis of new calix[4]arenes containing nucleoside bases

  摘要：

  A family of novel calix[4]arene derivatives containing nucleoside bases were designed and synthesized. Coupling reaction between para mono- or bis-amino calix[4]arenes 5,6 or 7 and thymin-1-ylacetic acid in the presence of DCC afforded mono- or bis-thymine-substituted calix[4]arenes 8, 9 or 10 in over 70% yield. Owing to the low solubility of adenine-N-9-ylacetic acid in DMF and DMSO and the weak nucleophilicity of aminocalix[4]arene derivatives, alternatively, the substitution reaction of bromoacetylated ammocalix[4]arenes derivatives 11, 12, 13 with adenine in the presence of sodium hydride was carried out to synthesize mono- or bis-adenine-substituted calix[4]arenes. Two kinds of isomers 15 and 16 or 17 and 18 were obtained due to the non-regiospecific alkylation of adenine, and their structures have been confirmed by C-13 NMR and H-1 NMR spectra. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00251-5
• 作为产物：
  描述：

  5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 在 aluminum (III) chloride 、 sodium hydride 作用下， 生成 25,26,27,28-tetradecyloxycalix<4>arene
  参考文献：
  名称：

  对膦酸杯芳烃和O-烷基化类似物作为潜在的杯芳烃基磷脂的合成与毒理学

  摘要：

  合成了一系列对膦酸杯[ n ]芳烃1 a–g，带有羟基，n = 4和5，或在其下缘n = 4处具有不同长度的烷基链，并对其进行了体外评估在大鼠PC12细胞中对细胞生存力的影响和混合视网膜细胞的原代培养。化合物1a和1g的下边缘带有羟基，对PC12细胞的毒性比对烷基化的化合物 低。浓度高达1 mg mL -1不会影响活细胞的数量。混合的视网膜培养物对所测试的所有杯芳烃显示出更高的对毒性作用的敏感性。化合物 1 b从甲苯溶液中自组装成纳米纤维，1 c从水溶液中组装成微胶粒，这些纳米级结构显示了其在多种生物学作用中的潜在应用，例如增溶对硝基苯酚和姜黄素。

  DOI：

  10.1002/cplu.201100081

文献信息

• The self-assembly of calix[4]arene derivatives based on an A-T base pairing
  作者：Cheng-Chu Zeng、Ya-Ling Tang、Qi-Yu Zheng、Li-Jun Huang、Bin Xin、Zhi-Tang Huang

  DOI：10.1016/s0040-4039(01)01215-1

  日期：2001.8

  Calix[4]arene derivatives with one adenine or thymine sidearm have been synthesized and their self-association characteristics which depend on solvent, temperature and concentrations are described. Mainly Watson–Crick A-T base pairing in these systems was detected using 1H NMR and ESI-MS.

  已经合成了带有一个腺嘌呤或胸腺嘧啶侧链的杯[4]芳烃衍生物，并描述了它们的自缔合特性，该特性取决于溶剂，温度和浓度。在这些系统中，主要使用1 H NMR和ESI-MS检测到Watson-Crick AT碱基配对。
• Synthesis of tetra-oligothiophene-substituted calix[4]arenes and their optical and electrochemical properties
  作者：Xiao Hua Sun、Chi Shing Chan、Man Shing Wong、Wai Yeung Wong

  DOI：10.1016/j.tet.2006.05.050

  日期：2006.8

  (raises HOMO level) of an oligothiophene within an assembly. It also stabilizes the formation of a radical cation, which results in an increase in the subsequent voltammetric oxidation and the occurrence of the higher oxidation states as compared to the monomeric counterparts. This assembly can serve as a model for the investigation of molecular interaction of π-conjugated systems.

  一种简便高效的方法，合成四寡噻吩取代的杯[4]芳烃，杯Calix-OT（n）与n使用钯催化的噻吩基溴化镁和溴取代的杯[4]芳烃的Kumada偶联作为关键步骤已开发出多达4个化合物。杯[4]芳烃组件中构造的四低聚噻吩的紧密接近导致峰/谱带展宽，光谱移位（即吸收光谱中的蓝移和发射光谱中的红移）以及荧光量子产率猝灭表示存在发色相互作用的单体。我们已经表明，发色内相互作用降低了装配体中寡噻吩的第一个电离（提高了HOMO水平）。与单体对应物相比，它还稳定了自由基阳离子的形成，这导致随后的伏安氧化增加，并出现更高的氧化态。
• Wide Rim Urethanes Derived from Calix[4]arenes:  Synthesis and Self-Assembly
  作者：Yudong Cao、Myroslav O. Vysotsky、Volker Böhmer

  DOI：10.1021/jo0524369

  日期：2006.4.1

  Calix[4]arenes 4, substituted at the wide rim by four N-tolyl-urethane groups, were synthesized, as well as derivatives 10a,b bearing two or three tolyl-urea groups beside of one or two urethane group(s). In contrast to tetra-tolyl urea 11, the urethane derivatives do not form hydrogen-bonded, dimeric capsules in CDCl3 or benzene-d6, but the dimerization can be induced for the triurea 10b by tetraethylammonium

  合成了在宽边缘上被四个N-甲苯基-氨基甲酸酯基团取代的杯[4]芳烃4，以及除了一个或两个氨基甲酸酯基团外还带有两个或三个甲苯基-尿素基团的衍生物10a，b。与四甲苯脲11相比，氨基甲酸酯衍生物不会在CDCl 3或苯-d 6中形成氢键键合的二聚体胶囊，但是三脲10b可以通过四乙基铵阳离子作为客体来诱导二聚化。苯-d中所有氨基甲酸酯4和10a，b均观察到异二聚体的定量形成在具有“四环”四脲14的混合物中，图6所示的化合物与图6中的“双环”四脲13混合，而“双环”四脲13需要二或三脲衍生物10a，b以进行干净的异二聚。
• Ikeda, Atsushi; Tsuzuki, Hirohisa; Shinkai, Seiji, Journal of the Chemical Society. Perkin transactions II, 1994, # 10, p. 2073 - 2080
  作者：Ikeda, Atsushi、Tsuzuki, Hirohisa、Shinkai, Seiji

  DOI：——

  日期：——
• Synthesis of new calix[4]arenes containing nucleoside bases
  作者：Cheng-Chu Zeng、Qi-Yu Zheng、Ya-Ling Tang、Zhi-Tang Huang

  DOI：10.1016/s0040-4020(03)00251-5

  日期：2003.3

  A family of novel calix[4]arene derivatives containing nucleoside bases were designed and synthesized. Coupling reaction between para mono- or bis-amino calix[4]arenes 5,6 or 7 and thymin-1-ylacetic acid in the presence of DCC afforded mono- or bis-thymine-substituted calix[4]arenes 8, 9 or 10 in over 70% yield. Owing to the low solubility of adenine-N-9-ylacetic acid in DMF and DMSO and the weak nucleophilicity of aminocalix[4]arene derivatives, alternatively, the substitution reaction of bromoacetylated ammocalix[4]arenes derivatives 11, 12, 13 with adenine in the presence of sodium hydride was carried out to synthesize mono- or bis-adenine-substituted calix[4]arenes. Two kinds of isomers 15 and 16 or 17 and 18 were obtained due to the non-regiospecific alkylation of adenine, and their structures have been confirmed by C-13 NMR and H-1 NMR spectra. (C) 2003 Elsevier Science Ltd. All rights reserved.