11,23-di-tert-butylcalix<4>arene-25,26,27,28-tetrol | 137571-15-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 11,23-di-tert-butylcalix<4>arene-25,26,27,28-tetrol
• 英文别名: 1,3-p-tert-butylcalix[4]arene；5,17-di-tert-butyl-25,26,27,28-tetrahydroxycalix[4]arene；25,26,27,28-tetrahydroxy-11,23-di-(tert-butyl)calix[4]arene；11,23-di-p-tert-butylcalix[4]arene；5,17-di-tert-butyl-25,27,26,28-tetrahydroxycalix[4]arene；5,17-Ditert-butylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaene-25,26,27,28-tetrol
• CAS: 137571-15-4
• 化学式: C₃₆H₄₀O₄
• 分子量: 536.711
• InChiKey: RQBAKMXRQPDQKP-UHFFFAOYSA-N

物化性质

• 沸点：
  635.3±55.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  40
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  11,23-di-tert-butylcalix<4>arene-25,26,27,28-tetrol 在 溴甲苯 copper diacetate 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 55.75h， 生成 22,31-Ditert-butyl-17,27,35,37-tetrakis(phenylmethoxy)-5,12-dioxahexacyclo[14.11.7.13,26.114,18.120,24.129,33]octatriaconta-1,3(36),14(38),15,17,20(37),21,23,26,29,31,33(35)-dodecaen-7,9-diyne
  参考文献：
  名称：

  Calixarenes: Selective Functionalization and Bridge Building

  摘要：

  The scope of the quinone methide method for introducing functional groups into the upper rim of calix[4]arenes has been expanded by taking advantage of selective esterification at the lower rim. A variety of calix[4]arenes carrying two functional groups on the upper rim have been prepared in this fashion, including compounds 12-25. Compound 25, containing a pair of propargyl groups, undergoes intramolecular oxidative coupling to yield the bridged compound 26. In like fashion the tetrasubstituted propargyl compound 7b undergoes both intramolecular and intermolecular oxidative coupling to give the doubly bridged calix[4]arene 27 and the doubly bridged bis-calix[4]arene 28.

  DOI：

  10.1021/jo00124a017
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 乙醇 、 重水 为溶剂， 反应 12.0h， 生成 11,23-di-tert-butylcalix<4>arene-25,26,27,28-tetrol
  参考文献：
  名称：

  Upper rim-functionalized calix[4]arene-based l-proline as organocatalyst for direct asymmetric aldol reactions in water and organic media

  摘要：

  The synthesis of upper rim-functionalized calix[4]arene-based L-proline was described, and its catalytic efficiency as organocatalyst for the enantioselective aldol reaction in water was investigated. The results showed that the nature of the hydrophobic cavity of calixarene is critical for catalytic activity in water. The products of the reaction between various ketones and aldehydes with anti-configuration were obtained in high yields (up to 94%) with high diastereo- (up to 95:5 dr) and enantioselectivities (up to 80% ee). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.063

文献信息

• Di-substituted azocalix[4]arenes containing chromogenic groups: synthesis, characterization, extraction, and thermal behavior
  作者：Serkan Elçin、Hasalettin Deligöz

  DOI：10.1016/j.tet.2013.06.018

  日期：2013.8

  In this study, the synthesis of chromogenic di-substituted azocalix[4]arene derivatives is described. Six novel azocalix[4]arenes (4a–f)were prepared by linking 4-methoxy, 4-methyl, 4-ethyl, 4-chloro, 4-bromo, and 4-nitroaniline to 25,26,27,28-tetrahydroxy-11,23-di-(tert-butyl)calix[4]arene through a diazo-coupling reaction, and were characterized by elemental analysis, FTIR, 1H NMR spectra and thermogravimetric

  在这项研究中，描述了生色二取代的偶氮杯[4]芳烃衍生物的合成。通过将4-甲氧基，4-甲基，4-乙基，4-氯，4-溴和4-硝基苯胺连接到25,26,27,28-四羟基制备了六种新颖的偶氮杯[4]芳烃（4a – f）通过重氮偶合反应得到-11,23-二叔丁基杯芳烃[4]芳烃，并用元素分析，FTIR，1 H NMR光谱和热重分析（TGA）进行了表征。通过液-液萃取某些金属阳离子（Sr 2 +，Ag +，Hg +，Hg 2 +，Co 2 +，Ni 2 +，Cu2+，Pb 2 +，Cr 3+，Al 3+）。已经观察到，二取代的偶氮杯[4]芳烃对Ag +，Hg +和Hg 2+离子具有很高的亲和力，但对其他金属几乎没有亲和力。比较了这些azocalix [4]芳烃的颜色，以了解不同pH值对吸收能力的影响。还通过热重分析（TG）和热分析（DTA）报告了这些化合物的热行为。
• Synthesis of calix[4]arene alkylamine derivatives as new phase-transfer catalysts for esterification reaction
  作者：Ezgi Akceylan、Mustafa Yilmaz

  DOI：10.1016/j.tet.2011.06.050

  日期：2011.8

  This study reports the synthesis of calix[4]arene-based phase-transfer catalysts derived from the reaction of 5,17-di-tert-butyl-25,27,26,28-tetrahydroxycalix[4]arene with N-ethylpiperazine, diallylamine or 4-benzylpiperidine. The catalytic efficiency of the calix[4]arenes alkylamine derivatives was evaluated by carrying out the ester-forming reaction of alkali metal carboxylates (sodium butyrate or

  这项研究报告了由5,17-二叔丁基-25,27,26,28-四羟基杯[4]芳烃与N-乙基哌嗪反应制得的杯芳烃[4]芳烃基相转移催化剂，二烯丙基胺或4-苄基哌啶。通过进行碱金属羧酸盐（丁酸钠或辛酸钠）与对硝基苄基溴的酯形成反应来评估杯[4]芳烃烷基胺衍生物的催化效率。已经发现，使用杯[4]芳烃的N-乙基哌嗪胺衍生物作为相转移催化剂，在25°C的条件下，碱金属羧酸盐与对硝基苄基溴的成酯反应提供了最佳收率。 。
• Calix[4]arene-based Mannich and Schiff bases as versatile receptors for dichromate anion extraction: synthesis and comparative studies
  作者：Asli Sap、Begum Tabakci、Aydan Yilmaz

  DOI：10.1016/j.tet.2012.08.015

  日期：2012.10

  A series of novel calix[4]arene-based Mannich (5 and 6) and Schiff base (9–11) receptors have been synthesized and characterized by various analytical techniques. Competitive two-phase extraction experiments of these novel calix[4]arene amine- and imine-containing derivatives revealed a strong affinity for dichromate anions (Cr2O72−/HCr2O7−). The protonated alkylinium form of 5, 6 and 9–11 proved to

  A [4]系列新颖的杯芳烃基曼尼希（5和6）和席夫碱（9 - 11）受体已经合成和表征通过各种分析技术。这些新颖的杯[4]芳烃胺和亚胺的衍生物的竞争性两相萃取实验表明对重铬酸根阴离子具有很强的亲和力（铬2个Ø72个-/六价铬2个Ø7-）。的质子化形式alkylinium 5，6和9 - 11被证明是有效的萃取剂，用于从含水重铬酸阴离子转移到有机相。另外，由提取重铬酸阴离子5和9在有竞争力的阴离子，如F的存在- ，氯- ，溴- ，不3-， 不2个-， 采购订单43- 和 所以42个-结果表明5和9可能是重铬酸根阴离子在存在这些阴离子时的选择性阴离子受体。
• Calix[4]tubes:  A New Class of Potassium-Selective Ionophore
  作者：Susan E. Matthews、Phillipe Schmitt、Vitor Felix、Michael G. B. Drew、Paul D. Beer

  DOI：10.1021/ja011856m

  日期：2002.2.1

  evaluated through the conformational change on binding by NMR studies. Selectivity of potassium complexation has been demonstrated using NMR and electrospray mass spectral techniques. Molecular modeling studies, derived from crystallographic data, confirm that the potassium metal cation is complexed via the axial route, passing through the calix[4]arene annulus, and provide evidence for complexation rate

  已经开发了一类基于双杯[4]芳烃结构的新型类隐窝离子载体。事实证明，这些分子对钾的络合选择性高于所有 I 族金属阳离子和钡。一系列对称和不对称杯[4]管的上缘具有烷基或苯基取代基，已以优异的产率合成。杯[4]芳烃上缘环境的改变可以微调钾吸收率，这可以通过核磁共振研究结合时的构象变化来评估。已使用 NMR 和电喷雾质谱技术证明了钾络合的选择性。来自晶体学数据的分子建模研究证实，钾金属阳离子通过轴向途径络合，穿过杯[4]芳烃环，
• Complexation of Cobalt(II) at the Upper Rim of Two New Calix[4]arene/Bipyridine-Based Podands
  作者：Jean-Olivier Dalbavie、Jean-Bernard Regnouf-de-Vains、Roger Lamartine、Sylvain Lecocq、Monique Perrin

  DOI：10.1002/(sici)1099-0682(200004)2000:4<683::aid-ejic683>3.0.co;2-n

  日期：2000.4

  Introduction of one or two 2,2′-bipyridine units at the upper rim of the calix[4]arene platform was performed by means of the Wittig reaction. The resulting alkenes were hydrogenated to give two new bipyridyl-based calixarene podands, which were studied as ligands for CoII cation. The mono-bipyridyldichlorocobalt complex was notably fully characterised by 1H-NMR and X-ray crystal structure analyses

  通过 Wittig 反应在杯 [4] 芳烃平台的上缘引入一个或两个 2,2'-联吡啶单元。将所得烯烃氢化以得到两种新的基于联吡啶基的杯芳烃 podands，将其作为 CoII 阳离子的配体进行研究。单联吡啶基二氯钴配合物通过 1H-NMR 和 X 射线晶体结构分析得到了显着的充分表征，证实了涉及联吡啶亚基和钴中心周围两个氯原子的四面体配位模式。