25,26,27,28-tetrahydroxy-11,23-di-(tert-butyl)-5,17-(4-methoxyphenylazo)calix[4]arene | 1446482-12-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 25,26,27,28-tetrahydroxy-11,23-di-(tert-butyl)-5,17-(4-methoxyphenylazo)calix[4]arene
• 英文别名: 5,17-Ditert-butyl-11,23-bis[(4-methoxyphenyl)diazenyl]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-dodecaene-25,26,27,28-tetrol
• CAS: 1446482-12-7
• 化学式: C₅₀H₅₂N₄O₆
• 分子量: 804.986
• InChiKey: HKIOAXXLTACELY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.1
• 重原子数：
  60
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  5,11,17,23-tetra-tert-butyl-25,27-dibenzoyloxy-26,28-dihydroxycalix<4>arene 在 aluminum (III) chloride 、 sodium acetate 、 sodium hydroxide 、 苯酚 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 44.0h， 生成 25,26,27,28-tetrahydroxy-11,23-di-(tert-butyl)-5,17-(4-methoxyphenylazo)calix[4]arene
  参考文献：
  名称：

  含显色基团的双取代偶氮杯[4]芳烃：合成，表征，提取和热行为

  摘要：

  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。

  DOI：

  10.1016/j.tet.2013.06.018

文献信息

• Synthesis and investigation of the properties of novel azocalix[4]arenes
  作者：H.H. Kart、A. Bayrakdar、S. Elcin、H. Deligoz、M. Karabacak

  DOI：10.1016/j.saa.2015.01.132

  日期：2015.7

  The azocalix[4]arenes molecules such as methylphenylazocalix[4]aren (MPcalix[4]) and methoxyphenylazocalix[4]aren (MOPcalix[4]) have been synthesized and characterized by experimental FT-IR and H-1 NMR spectral analyses. The fundamental vibrational transitions have been addressed by experimental FF-IR (4000-400 cm(-1)) technique and density functional theory (DFT) employing B3LYP level with the 6-31G(d) and 6-311G(d,p) basis sets. The H-1 NMR spectra of the studied compounds have been recorded in chloroform, and compared with computed data obtained by using gauge including atomic orbital (GIAO) method. Furthermore, thermodynamic properties (heat capacity, entropy, and enthalpy changes) and frontier molecular orbitals of the molecules in the ground state have been Calculated by using the same method and basis sets. The non-linear optical properties such as the first order hyperpolarizability (beta(o)), related properties (alpha(0) and Delta(alpha)) are also computed. Information about the charge density distribution of the molecules and its chemical reactivity has been studied by mapping molecular electrostatic potential surface (MEPs). The scaled vibrational frequency values have been compared with experimental FT-IR spectroscopic data. The correlations between the observed and calculated frequencies are in good agreement with each other as well as the correlation of NMR data. The linear polarizability and first hyperpolarizability of the studied molecules indicate that the compounds are a good candidate of nonlinear optical materials. (C) 2015 Elsevier B.V. All rights reserved.