partial-cone-7,15,23-tri-tert-butyl-25,26,27-tris(N,N-diethylaminocarbonylmethoxy)-2,3,10,11,18,19-hexahomo-3,11,19-trioxacalix<3>arene | 252284-83-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: partial-cone-7,15,23-tri-tert-butyl-25,26,27-tris(N,N-diethylaminocarbonylmethoxy)-2,3,10,11,18,19-hexahomo-3,11,19-trioxacalix<3>arene
• 英文别名: cone-7,15,23-tri-tert-butyl-25,26,27-tris(N,N-diethylaminocarbonylmethoxy)-2,3,10,11,18,19-hexahomo-3,11,19-trioxacalix<3>arene；7,15,23-tri-tert-butyl-25,26,27-tris[(N,N-diethylaminocarbonyl)methoxy]-2,3,10,11,18,19-hexahomo-3,11,19-trioxacalix[3]arene；cone-7,15,23-tri-tert-butyl-25,26,27-tris[(N,N-diethylaminocarbonyl)methoxy]-2,3,10,11,18,19-hexahomo-3,11,19-trioxacalix[3]arene；N,N-diethyl-2-[[7,15,23-tritert-butyl-26,27-bis[2-(diethylamino)-2-oxoethoxy]-3,11,19-trioxatetracyclo[19.3.1.15,9.113,17]heptacosa-1(24),5,7,9(27),13(26),14,16,21(25),22-nonaen-25-yl]oxy]acetamide
• CAS: 252284-83-6
• 化学式: C₅₄H₈₁N₃O₉
• 分子量: 916.252
• InChiKey: TZAUQKGJVHEREE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  66
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  partial-cone-7,15,23-tri-tert-butyl-25,26,27-tris(N,N-diethylaminocarbonylmethoxy)-2,3,10,11,18,19-hexahomo-3,11,19-trioxacalix<3>arene 在 sodium hydroxide 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 112.0h， 生成 12,20,28-Tritert-butyl-5,8,16,24,32,35,40,43,47-nonaoxaheptacyclo[20.16.6.310,30.13,37.09,14.018,44.026,31]octatetraconta-1(38),2,9(14),10,12,18,20,22(44),26(31),27,29,37(45)-dodecaene-6,34,41-trione
  参考文献：
  名称：

  Synthesis and Inclusion Properties ofC3-Symmetrically Capped Hexahomotrioxacalix[3]arenes with Ester Groups on the Lower Rim

  摘要：

  A triply bridged capped hexahomotrioxacalix[3]arene 4 with C-3-symmetry was synthesized by treatment of hexahomotrioxacalix[3]arene tricarboxylic acid 3 with 1,3,5-tris(bromomethyl)benzene in the presence of Na2CO3 in DME The complexation modes of 4 with cations differed according to the ionic size and properties of the guest cations, as was clearly elucidated by H-1 NMR titration spectra. Conformational studies on 4 in solution and in the solid state are also described.

  DOI：

  10.1002/1099-0690(200103)2001:6<1069::aid-ejoc1069>3.0.co;2-r
• 作为产物：
  描述：

  p-(tert-butyl)hexahomotrioxacalix[3]arene 、 N,N-二乙基-2-氯乙酰胺 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以85%的产率得到partial-cone-7,15,23-tri-tert-butyl-25,26,27-tris(N,N-diethylaminocarbonylmethoxy)-2,3,10,11,18,19-hexahomo-3,11,19-trioxacalix<3>arene
  参考文献：
  名称：

  Synthesis, structure and inclusion properties of cone-tris{[(5′-methyl-2,2′-bipyridyl)-5-yl]oxycarbonylmethoxy}hexahomotrioxacalix[3]arene

  摘要：

  制备了具有锥形构象的[(5′-甲基-2,2′-联吡啶)-5-基]氧羰基甲氧基的六方三氧杂喹喔啉[3]炔，它对 Ag+ 有很强的亲和力，是 Ag+ 和 nBuNH3 + 的二位受体。在 Ag+ 与之络合的过程中，观察到 2,2′-联吡啶基的构象发生了变化，从原来环氮的外向型转变为朝向硫杂蒽空腔的内向型。

  DOI：

  10.1007/s10847-011-9936-3

文献信息

• Specific Binding of Primary Ammonium Ions and Lysine-Containing Peptides in Protic Solvents by Hexahomotrioxacalix[3]arenes
  作者：Simon Lambert、Kristin Bartik、Ivan Jabin

  DOI：10.1021/acs.joc.0c01294

  日期：2020.8.7

  H-bonds with the ethereal macrocycle. The remarkable electronic, size, and shape complementarity between primary ammonium ions and the two cavity-based receptors leads to an unprecedented specificity for primary ammonium ions over secondary, tertiary, and quaternary ones. These binding properties were exploited for the selective liquid–liquid extraction of primary ammonium salts from water and for the

  使用NMR光谱法和计算机模拟方法研究了两个基于草胺磷[3]亚芳基的受体对铵离子的结合。即使在质子环境中，这两种受体也显示出内在复杂的多种初级铵离子，包括生物分子。对于所有来宾，氨离子深深插入多环芳族腔及其NH 3 +头几乎在18-crown-3部分的三个氧原子所定义的平面内，因此使其能够与醚大环建立三个H键。伯铵离子与两个基于空穴的受体之间的显着电子，大小和形状互补性，导致伯铵离子相对于仲，叔和季铵离子具有前所未有的特异性。这些结合特性被用于从水中选择性地液-液萃取伯铵盐，以及选择性识别含赖氨酸的肽，为肽传感领域开辟了新的前景。
• The Effects of O-Substituents of Hexahomotrioxacalix[3]arene on Potentiometric Discrimination between Dopamine and Biological Organic/Inorganic Cations
  作者：Ryosuke Saijo、Hiroyuki Murakami、Saori Tsunekawa、Souhei Imanishi、Naohiro Shirai、Shin-ichi Ikeda、Kazunori Odashima

  DOI：10.1248/cpb.55.417

  日期：——

  displays a high potentiometric selectivity for dopamine over, not only other catecholamines (noradrenaline, adrenaline), but also quaternary ammonium guests (tetramethylammonium, choline, and acetylcholine) and inorganic cations (Na+, K+, NH4+). Interestingly, changes in membrane potential based on the host-guest complexation of host 2 that were observed dopamine/inorganic cation selectivity were

  作为在膜表面的一种有趣的分子识别方法，六高三氧杂lix [3]芳烃的三邻乙酸酯（主体2）在掺入聚氯乙烯（PVC）液膜中时显示出高电位选择性对于多巴胺，不仅是其他儿茶酚胺（去甲肾上腺素，肾上腺素），还包括季铵客体（四甲基铵，胆碱和乙酰胆碱）和无机阳离子（Na +，K +，NH4 +）。有趣的是，包含酰胺取代基的相关主体3和4未显示出基于多巴胺/无机阳离子选择性观察到的主体2的主体-客体-客体络合的膜电位变化。本文介绍了我们的工作，以分别估算影响多巴胺选择性的两个因素，即 客体亲脂性因子和主体-客体复合因子，以试图了解这些主体的O-取代基的作用。电位实验表明，尽管客人的亲脂性大致相等，但宿主2对多巴胺的电动势（EMF）响应却非常好。此外，主机2显示了ca。与去甲肾上腺素，肾上腺素，K +和NH4 +阳离子相比，多巴胺的复合作用强20倍。这些结果表明，离子选择电极对多巴胺的高电位选择性主要反映了
• Syntheses and ion selectivities of tri-amide derivatives of hexahomotrioxacalix[3]arene. Remarkably large metal template effect on the ratio of cone vs. Partial-cone conformers
  作者：Hitoshi Matsumoto、Shoko Nishio、Michinori Takeshita、Seiji Shinkai

  DOI：10.1016/0040-4020(95)00165-5

  日期：1995.4

  We have found that a homotrioxacalix[3]arene (1H3) -based ionophore with a cone conformation, which is very difficult to obtain by the reaction of 1H3 and ethyl bromoacetate, can be synthesized quantitatively by the reaction of 1H3 and N,N-diethylchloroacetamide in THF in the presence of NaH. The conformer distribution of the tri-amide derivative (1Am3) between cone and partial-cone was sensitively

  我们已经发现，通过1H 3和溴乙酸乙酯反应很难获得的，具有圆锥构象的均三恶唑基[3]芳烃（1H 3）基离子载体，可以通过1H 3和N的反应定量地合成。在NaH存在下，N-二乙基氯乙酰胺在THF中的溶液。锥孔和部分锥孔之间的三酰胺衍生物（1Am 3）的构象分布受金属模板效应的影响在0〜100 ％范围内。圆锥体1Am 3对碱金属和碱土金属阳离子显示出很高的亲和力。特别是，它与几乎不与三酯衍生物结合的碱土金属阳离子形成稳定的络合物。结果表明，由于以C 3-对称性排列的三个配位酰胺基，cone-1Am 3可作为优异的中性离子载体。
• New fluorescent sensor for antimony and transition metal cations based on rhodamine amide-arm homotrioxacalix[3]arene
  作者：Chong Wu、Wen-Juan Zhang、Xi Zeng、Lan Mu、Sai-Feng Xue、Zhu Tao、Takehiko Yamato

  DOI：10.1007/s10847-009-9665-z

  日期：2010.2

  A new fluorescent sensor 1 based on the rhodamine amide-armed homotrioxacalix[3]arene was synthesized, and its sensing behavior toward metal ions was investigated by UV–vis and fluorescence spectroscopies. Upon the addition of metal cations (Sb3+, Fe3+, Ni2+), a significant fluorescent enhancement in the range of 500–600 nm and colorimetric change was observed.

  基于罗丹明酰胺基化的同三氧杂环[3]芳烃的新型荧光传感器1被合成，并通过紫外-可见光和荧光光谱对其对金属离子的感应行为进行了研究。在添加金属阳离子（Sb3+、Fe3+、Ni2+）后，在500-600纳米范围内观察到明显的荧光增强和色度变化。
• A pyrenyl-appended C-symmetric hexahomotrioxacalix[3]arene for selective fluorescence sensing of iodide
  作者：Hai-Fang Xie、Chong Wu、Juan Zou、Ya-Xin Yang、Hong Xu、Qi-Long Zhang、Carl Redshaw、Takehiko Yamato

  DOI：10.1016/j.dyepig.2020.108340

  日期：2020.7

  A new C-3v-symmetric hexahomotrioxacalix[3]arene L bearing pyrene moieties as fluorophores has been designed and synthesized. L exhibits a significant fluorescence quenching response to I- even when in the presence of other potentially competing anions. There is a good linear relationship between the fluorescence intensity and the concentration of I- over the range 0-100 mu M and the detection limit was calculated to be as low as 164 nM. Ligand L can serve as a fluorescent chemosensor for the highly selective, sensitive, and rapid detection of I-.