26,28-dimethoxycalix[4]arene-25,27-diol | 1021694-88-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 26,28-dimethoxycalix[4]arene-25,27-diol
• 英文别名: 25,27-dimethoxy-26,28-dihydroxycalix[4]arene；25,27-dihydroxy-26,28-dimethoxycalix[4]arene；26,28-dimethoxypentacyclo[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-25,27-diol
• CAS: 1021694-88-1
• 化学式: C₃₀H₂₈O₄
• 分子量: 452.55
• InChiKey: ZNWQKXNYIPOPPR-UHFFFAOYSA-N

物化性质

• 沸点：
  636.1±55.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  26,28-dimethoxycalix[4]arene-25,27-diol 在 氯化亚砜 、 硼烷 、 potassium tert-butylate 、 sodium hydride 、 臭氧 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 11,23-Bis(chloromethyl)-26,28-dimethoxypentacyclo<19.3.1.1^3,7.1^9,13.1^15,19>octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-25,27-diol
  参考文献：
  名称：

  杯[4]芳烃在上缘的选择性功能化

  摘要：

  描述了通过转移功能和在苯酚环对位的选择性取代在上边缘对杯[4]芳烃进行选择性径向官能化的方法。描述了26,28-二甲氧基-11,23-二硝基杯[4]芳烃的晶体结构。

  DOI：

  10.1016/s0040-4039(00)99097-x
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 反应 0.25h， 生成 26,28-dimethoxycalix[4]arene-25,27-diol
  参考文献：
  名称：

  Synthesis and Properties ofO-Glycosyl Calix[4]Arenes (Calixsugars)

  摘要：

  AbstractModelO‐glycosylation reactions at either rim of calix[4]arenes are described with the aim of providing access to a new family of carbohydrate‐containing calixarene derivatives named calixsugars. One or two sugar moieties (D‐mannofuranose and D‐glucopyranose) were introduced at the lower rim of the parent calix[4]arene by glycosylation of the phenolic hydroxyl groups by means of a Mitsunobu reaction. Tetrapropoxy calix[4]arenes bearing two or four hydroxymethyl groups at the upper rim were coupled with perbenzoylated thioethyl D‐galactoside and D‐lactoside in the presence of the thiophilic promoter copper(III) triflate. In this way β‐linked bis‐ and tetrakis‐O‐galactosyl calix[4]arenes were obtained in good yield, the latter showing some solubility in water. For theO‐lactosyl derivatives only the bis‐substituted compound could be obtained because of the competing formation of an intramolecular ether linkage between 1,3‐hydroxymethyl groups. Preliminary binding studies showed some affinity of the galactose‐containing calixsugars toward charged carbohydrates and dihydrogen phosphate anion.

  DOI：

  10.1002/chem.19970031108

文献信息

• Microwave-assisted synthesis of 1,3-dialkyl ethers of calix[4]arenes: application to the synthesis of cesium selective calix[4]crown-6 ionophores
  作者：Sandip K. Nayak、Manoj K. Choudhary

  DOI：10.1016/j.tetlet.2011.10.142

  日期：2012.1

  phenolic-OH groups of calix[4]arenes with various alkyl halides/tosylates and K2CO3 under microwave irradiation afforded 1,3-dialkoxycalix[4]arenes in their cone conformation only as predominant/sole product in good yields (71–85%). The protocol was found to be much superior to conventional heating both in terms of yield and reaction time. Some of the 1,3-dialkoxycalix[4]arenes were elaborated further

  微波辐射下杯[4]芳烃的苯酚-OH基与各种烷基卤化物/甲苯磺酸酯和K 2 CO 3的部分醚化，仅以主要/单一产物的形式提供1,3-二烷氧基杯[4]芳烃，其圆锥构象仅为高收率（71–85％）。发现该方案在产率和反应时间方面均比常规加热好得多。一些1,3-二烷氧基杯[4]芳烃被进一步精制为铯选择性杯[4]冠6离子载体的合成。
• Calix[4]arene based neutral receptor for dihydrogen phosphate anion
  作者：Har Mohindra Chawla、Suneel Pratap Singh

  DOI：10.1016/j.tet.2007.11.010

  日期：2008.1

  A series of novel calix[4]arene hydrazone and semicarbazone based neutral receptors have been synthesized and characterized by IR, UV–vis, and NMR spectroscopies. The preliminary UV–vis and 1H NMR titration experiments revealed that 25,26,27,28-tetrapropoxycalix[4]arene tetra-semicarbazone can recognize H2PO4− through a 1:1 binding-stoichiometry in preference over other anions (Cl−, Br−, I−, HSO4−

  合成了一系列新颖的杯[4]芳烃和半脲基中性受体，并通过红外，紫外-可见和核磁共振谱进行了表征。初步UV-vis和1个1 H NMR滴定实验揭示，25,26,27,28-tetrapropoxycalix [4]芳烃四缩氨基脲可以识别ħ 2 PO 4 -通过1：优先于其它阴离子1结合化学计量（氯- ，溴- ，我-，HSO 4 -，CLO 4 - ，和CH 3 COO - ）。
• Calix[4]arenes Containing Ferrocene Amide as Carboxylate Anion Receptors and Sensors
  作者：Boosayarat Tomapatanaget、Thawatchai Tuntulani、Orawon Chailapakul

  DOI：10.1021/ol034355+

  日期：2003.5.1

  Calix[4]arene derivatives containing amide ferrocene units at the wide rim and ethyl ester groups at the narrow rim, L1-L3, were synthesized and their anion binding and sensing properties were investigated. It was found from (1)H NMR titrations that L1-L3 were able to bind selectively with carboxylate anions. Moreover, cyclic voltammetry and square wave voltammetry showed that L1-L3 were able to act

  合成了杯状[4]芳烃衍生物，其在宽边缘含有酰胺二茂铁单元，在窄边缘含有乙基酯基，L1-L3，并研究了它们的阴离子结合和传感性能。从（1）H NMR滴定中发现，L1-L3能够选择性地与羧酸根阴离子结合。此外，循环伏安法和方波伏安法表明，L1-L3可以作为羧酸根阴离子的电化学传感器。[结构：见文字]
• Accessible gold clusters using calix[4]arene N-heterocyclic carbene and phosphine ligands
  作者：Michael M. Nigra、Alexander J. Yeh、Alexander Okrut、Antonio G. DiPasquale、Sheila W. Yeh、Andrew Solovyov、Alexander Katz

  DOI：10.1039/c3dt50804h

  日期：——

  Au11-sized clusters after reduction of both complexes. The new cluster, like the one reported with the tert-butyl analog, has an extraordinary 25% of surface atoms that are open and accessible to a 2-NT (2-naphthalenethiol) probe in solution. We also investigated the effect of calix[4]arene lower-rim substituents that coordinate to the metal, by using N-heterocyclic carbene (NHC) functional groups rather than

  我们研究了由开放的“配位不饱和”活性位点组成的可接近的杯[4]芳烃结合金簇的合成，使用依赖于的比较方法 杯[4]芳烃具有各种上边缘和下边缘取代基的配体。与报道的 Au( I )-叔丁基-杯芳烃膦复合物相比，它在溶液中表现出单个锥形构象异构体，H 上缘类似物在溶液中表现出多个构象异构体。这与叔丁基上边缘类似物的观察结果形成对比，后者在类似条件下在溶液中表现出单一的锥形构象异构体。在固态下，通过单晶 X 射线衍射测定，H 和叔-丁基上缘类似物仅表现出锥形构象异构体。对这两种固态结构的详细结构分析强调了 CH-π 相互作用，其中涉及 P 上的甲氧基下环取代基和苯基取代基，这是在 P的同一侧强制 Au( I ) 原子的紧密构型的关键特征。杯[4]芳烃下缘平面。我们假设这种配置促进了配体与金表面的螯合，并在两种复合物还原后促进了小的 Au 11大小的簇的合成。新的簇，就像用叔丁基类似物报道的那个簇一样，有非常多的
• Electric Field Effects of Photogenerated Ion Pairs on Nearby Molecules: A Model for the Carotenoid Band Shift in Photosynthesis
  作者：David Gosztola、Hiroko Yamada、Michael R. Wasielewski

  DOI：10.1021/ja00112a018

  日期：1995.2

  during the 3.7 ns lifetime of the photogenerated ion pair. The magnitude of this shift depends on the dielectric constant of the surrounding solvent. The data are used to calculate an electric field strength of about 5.5 MV/cm at the carotenoid in toluene. The magnitude of the electric field produced by the ion pair at the carotenoid is larger than the highest fields that can be applied externally. 32

  具有 8.4 A 中心到中心距离和线性取向的锌卟啉电子供体-均苯四甲酰亚胺电子受体对内的光致电荷分离显示出对附近类胡萝卜素分子的基态吸收光谱产生大的电致变色效应。相对于光生离子对产生的电场方向，类胡萝卜素的 CC 主链的方向受到限制。这是通过用杯[4]芳烃桥将电子供体-受体对与类胡萝卜素共价连接来实现的。桥保持其锥形构象，导致供体-受体轴和类胡萝卜素的 CC 骨架之间的平均二面角为 35°。使用皮秒瞬态吸收光谱，在光生离子对的 3.7 ns 寿命期间，很容易观察到类胡萝卜素基态吸收光谱的 15 nm 电致变色红移。这种偏移的大小取决于周围溶剂的介电常数。该数据用于计算甲苯中类胡萝卜素的电场强度约为 5.5 MV/cm。类胡萝卜素处的离子对产生的电场强度大于外部施加的最高电场。32 个参考文献，更多 » 6 个无花果，1 个标签。« 更少 甲苯中的类胡萝卜素为 5 MV/cm。类胡萝卜素处的