5,11,17,23-Tetratert-butyl-26,28-bis(2-phenylethynyl)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-25,27-diol | 868840-71-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5,11,17,23-Tetratert-butyl-26,28-bis(2-phenylethynyl)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-25,27-diol
• CAS: 868840-71-5
• 化学式: C₆₀H₆₄O₂
• 分子量: 817.167
• InChiKey: HRCVIYWQQYGKCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.7
• 重原子数：
  62
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,11,17,23-Tetratert-butyl-26,28-bis(2-phenylethynyl)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-25,27-diol 以 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Photochemical Cycloisomerizations via 7-exo-dig Reactions on a Calix[4]arene Scaffold

  摘要：

  Narrow-rim 1,3-bis(phenylethynyl)-p-tert-butylcalix[4]arenes were found to be photolabile, producing unprecedented seven-membered oxacyclic systems formed via 7-exo-dig cyclizations and a new [3.2.1]bicyclic system via subsequent 1,8-H shifts. The calixarene provided a scaffold for these unprecedented photochemical reactions to occur.

  DOI：

  10.1021/jo070236m
• 作为产物：
  描述：

  5,11,17,23-tetra-tert-butyl-26,28-diiodopentacyclo[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-dodecane-25,27-diol 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以64%的产率得到5,11,17,23-Tetratert-butyl-26,28-bis(2-phenylethynyl)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-25,27-diol
  参考文献：
  名称：

  Narrow-Rim Functionalization of Calix[4]arenes via Sonogashira Coupling Reactions

  摘要：

  The narrow (or "lower")-rim hydroxyl groups of calixarenes are known to be resistant to substitution/displacement. The Sonogashira coupling reaction with TMSA and phenylacetylene, however, has now been extended to the bistriflate of p-tert-butylcalix[4]arene, previously known to be resistant to Stille, Neigishi, or Suzuki-Miyaura reactions. Under some of the reaction conditions investigated, the previously unknown narrow-rim mono- and diiodo-p-tert-butylcalix[4]arene products were also produced, in addition to the narrow-rim mono- and dialkynyl products. Homocoupling of the narrow-rim monoethynyl-p-tert-butyl-calix[4]arene produced a new narrow-rim rigid butadiyne-linked bis-p-tert-butylcalix[4]arene.

  DOI：

  10.1021/jo050488s

文献信息

• Alkynyl Expanded Donor–Acceptor Calixarenes: Geometry and Second-Order Nonlinear Optical Properties
  作者：Gunther Hennrich、Ma Teresa Murillo、Pilar Prados、Hassan Al-Saraierh、Abdelmeneim El-Dali、David W. Thompson、Julie Collins、Paris E. Georghiou、Ayele Teshome、Inge Asselberghs、Koen Clays

  DOI：10.1002/chem.200700615

  日期：2007.9.17

  With respect to their optical properties, these donor-acceptor systems are treated as ensembles of covalently linked, electronically independent tolane subchromophores. Linear UV/visible and fluorescence spectroscopic investigations revealed that the charge-transfer character of the electronic transitions in calixarenes, and also the second-order nonlinear optical (NLO) properties depend on the electron-withdrawing

  通过Sonogashira偶联合成了许多宽边和窄边的官能化炔基杯[4]芳烃。就其光学性质而言，这些供体-受体系统被视为共价连接的，电子独立的二亚砜基团的集合体。线性紫外/可见和荧光光谱研究表明，杯芳烃中电子跃迁的电荷转移特性以及二阶非线性光学（NLO）性质取决于末端乙炔基苯基取代基（NO（2 ），CF（3），H）。硝基衍生物显示出二次超极化率β的高值。目标化合物的（非线性）光学特性不仅取决于亚发色团的数量和相对位置，而且还包括杯形芳烃的几何形状。特别地，可以通过杯芳烃支架的取代模式（宽-窄边缘取代-窄边缘取代）和引入的乙炔官能团的数目来确定杯芳烃腔的打开角度。NLO性质和构象问题都可以通过在溶液中使用超瑞利散射（HRS）方便地进行评估，并得到固态X射线晶体学的支持。
• Tunable π-Interactions in Monomeric Organozinc Complexes:  Solution and Solid-State Studies
  作者：Ella Bukhaltsev、Israel Goldberg、Revital Cohen、Arkadi Vigalok

  DOI：10.1021/om070213y

  日期：2007.7.30

  A series of the calix[4]arene ligands, partially oxygen-depleted at the 1 and 3 positions via the Sonogashira cross-coupling reaction with several arylacetylenes, were prepared. Upon reaction with R2Zn (R = Me, Et, C6F5), the corresponding organozinc complexes were obtained. X-ray analysis showed weak π-interactions between the organozinc fragment and the triple bonds. In addition, the solution 13C

  制备了一系列杯[4]芳烃配体，它们通过与几种芳基乙炔的Sonogashira交叉偶联反应在1和3位上部分耗氧。与R 2 Zn（R = Me，Et，C 6 F 5）反应后，获得相应的有机锌配合物。X射线分析表明，有机锌片段和三键之间的π相互作用较弱。另外，解决方案1313 C NMR研究表明，这些相互作用的强度与乙炔基团的电子密度之间具有良好的相关性，富电子的炔烃与锌中心的结合力更强。后者也得到了模型化合物上DFT计算的支持。这些结果表明，尽管溶液，固态，有机锌化合物的π-相互作用虽然微弱，但仍可观察到并进行微调。