5,11,17,23-Tetramethyl-2,8,14,20-tetrapentylpentacyclo[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-4,6,10,12,16,18,22,24-octol | 134731-88-7

• 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-Tetramethyl-2,8,14,20-tetrapentylpentacyclo[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-4,6,10,12,16,18,22,24-octol
• CAS: 134731-88-7
• 化学式: C₅₂H₇₂O₈
• 分子量: 825.139
• InChiKey: JNTJZNFKXPFJFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.3
• 重原子数：
  60
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  162
• 氢给体数：
  8
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  溴氯甲烷 、 5,11,17,23-Tetramethyl-2,8,14,20-tetrapentylpentacyclo[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-4,6,10,12,16,18,22,24-octol 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以96%的产率得到6,12,18,39-Tetramethyl-25,29,33,37-tetrapentyl-2,4,8,10,14,16,20,22-octaoxanonacyclo[21.15.1.124,38.05,36.07,34.011,32.013,30.017,28.019,26]tetraconta-1(39),5,7(34),11,13(30),17(28),18,23,26,31,35,38(40)-dodecaene
  参考文献：
  名称：

  间苯二芳烃空洞分子的选择性官能化；远端功能化空洞的单晶X射线结构

  摘要：

  从四（溴甲基）cavitands开始，描述了一种用于间苯二甲烯cavitands选择性功能化的新方法。

  DOI：

  10.1016/0040-4039(96)01027-1
• 作为产物：
  描述：

  2,6-二羟基甲苯 、 正己醛 以90%的产率得到5,11,17,23-Tetramethyl-2,8,14,20-tetrapentylpentacyclo[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-4,6,10,12,16,18,22,24-octol
  参考文献：
  名称：

  间苯二芳烃空洞分子的选择性官能化；远端功能化空洞的单晶X射线结构

  摘要：

  从四（溴甲基）cavitands开始，描述了一种用于间苯二甲烯cavitands选择性功能化的新方法。

  DOI：

  10.1016/0040-4039(96)01027-1

文献信息

• Novel Resorcinarene Cavitand-Based CMP(O) Cation Ligands:  Synthesis and Extraction Properties
  作者：Harold Boerrigter、Willem Verboom、David N. Reinhoudt

  DOI：10.1021/jo9703414

  日期：1997.10.1

  complexation with Eu(picrate)(3) (K(ex)(1) = 2.7 x 10(12) M(-)(4)). The steric preorganization of the four CMP(O) moieties on the resorcinarene cavitand improves the efficiency and selectivity [of Eu(III) over UO(2)(II) and Fe(III)] of the metal extraction processes, compared to simple CMP(O) extractants.

  从四（溴甲基）cavitand 3开始合成了四官能化的间苯二芳基cavitands（4-6）。新的基于cavitand的阳离子配体具有（氨基甲酰基甲基）膦酸酯（CMP）和-膦氧化物（CMPO）部分（8a，b和9a，b） ）是通过两条不同的路线制备的，总收率良好（45-86％）。配体（8a，b和9b）是非常有效的euro提取剂。Ph（2）CMPON（Pr）-cavitand 8b具有最高的提取常数，通过放射性示踪剂实验确定，与Eu（苦味酸）（3）1：1络合（K（ex）（1）= 2.7 x 10（12）） M（-）（4））。与简单的CMP相比，间苯二甲烯空洞上的四个CMP（O）部分的空间预组织可提高[Eu（III）对UO（2）（II）和Fe（III）的效率和选择性] （O）萃取剂。
• A facile synthetic route to convert Tb(<scp>iii</scp>) complexes of novel tetra-1,3-diketone calix[4]resorcinarene into hydrophilic luminescent colloids
  作者：Nataliya A. Shamsutdinova、Sergey N. Podyachev、Svetlana N. Sudakova、Asiya R. Mustafina、Rustem R. Zairov、Vladimir A. Burilov、Irek R. Nizameev、Ildar Kh. Rizvanov、Victor V. Syakaev、Bulat M. Gabidullin、Sergey A. Katsuba、Aidar T. Gubaidullin、Georgy M. Safiullin、Wim Dehaen

  DOI：10.1039/c4nj00637b

  日期：——

  Luminescent hydrophilic core–shell nanoparticles are synthesized through reprecipitation and polyelectrolyte deposition techniques from Tb(iii) complexes.

  通过重新沉淀和聚电解质沉积技术，利用Tb(iii)配合物合成了发光亲水性核壳纳米颗粒。
• Supramolecular surface plasmon resonance (SPR) sensors for organophosphorus vapor detection
  作者：Susan M. Daly、Michele Grassi、Devanand K. Shenoy、Franco Ugozzoli、Enrico Dalcanale

  DOI：10.1039/b615516b

  日期：——

  We synthesized cavitands containing COOH moieties at the upper rim of the cavity and evaluated the interaction between these cavitands and the sarin nerve gas simulant, dimethylmethylphosphonate (DMMP) using surface plasmon resonance (SPR) spectroscopy. The carboxylic acid group on the cavitand is expected to form a hydrogen bond with the PO group of the organophosphorus vapors. Films of these cavitands produced a rapid and reversible SPR response to low concentrations of DMMP. We observed concentration dependent sorption of the DMMP molecule into the COOH containing layer in the ppb to ppm range. Spin-cast films and Langmuir–Blodgett (LB) depositions of bilayer thick cavitand films produced identical SPR shifts upon exposure to DMMP. The sensitivity of the sensor was enhanced via LB deposition of multiple bilayers. Eight-layer-thick films of the COOH cavitand showed sensitivity to DMMP concentrations as low as 16 ppb. The orientation of the COOH group into or out of the cavity did not affect DMMP binding, but strongly influenced the water uptake. In both cases the molecular recognition event responsible for the DMMP uptake has been elucidated via crystal structure analyses of the complexes of COOH in/out cavitands with DMMP. Furthermore, we demonstrated that the COOH containing cavitand had an SPR sensitivity to DMMP higher than the standard fluoropolyol sensing layer, and that the cavitand layer was less prone to water vapor and alcohol interferences. Hence, cavitand layers containing a COOH moiety are promising for use as sensitive and specific sensors for nerve gas agents.

  我们在空腔上缘合成了含有 COOH 部分的空配体，并使用表面等离子体共振 (SPR) 光谱评估了这些空配体与沙林神经毒气模拟物二甲基膦酸二甲酯 (DMMP) 之间的相互作用。空配体上的羧酸基团预计会与有机磷蒸气的 PO 基团形成氢键。这些空配体薄膜对低浓度的 DMMP 产生快速且可逆的 SPR 响应。我们观察到 DMMP 分子在 ppb 至 ppm 范围内吸附到含 COOH 层中的浓度依赖性。旋涂薄膜和双层厚空腔薄膜的朗缪尔-布洛杰特 (LB) 沉积在暴露于 DMMP 时产生相同的 SPR 位移。通过多个双层的LB沉积增强了传感器的灵敏度。八层厚的 COOH 空穴体薄膜显示出对低至 16 ppb 浓度的 DMMP 的敏感性。 COOH 基团进出空腔的方向不影响 DMMP 结合，但强烈影响水的吸收。在这两种情况下，通过 COOH 输入/输出空穴与 DMMP 复合物的晶体结构分析，阐明了负责 DMMP 吸收的分子识别事件。此外，我们还证明，含有 COOH 的空穴配体对 DMMP 的 SPR 敏感性高于标准含氟多元醇传感层，并且空穴配体层不易受到水蒸气和酒精的干扰。因此，含有 COOH 部分的空穴层有望用作神经毒气剂的敏感和特异性传感器。
• Vases and kites as cavitands
  作者：John R. Moran、John L. Ericson、Enrico Dalcanale、Judi A. Bryant、Carolyn B. Knobler、Donald J. Cram

  DOI：10.1021/ja00015a026

  日期：1991.7

  The syntheses, characterizations, and substituent effects on the vase vs kite conformations of 1-17 are described. These compounds are assembled by two-step syntheses from resorcinol (or 2-substituted derivatives) and aldehydes to form octols 18-26 in high yields, followed by 4-fold bridging reactions with quinoxalines 27-29 or pyrazine 30. In the crystal structure of 3.2CH2Cl2, one CH2Cl2 is enclosed in the vase cavity, while a second CH2Cl2 iS found surrounded by the four (CH2)4Cl groups. When the 2-position of resorcinol is hydrogen, only the vase form of the cavitands exists at 25-degrees-C or higher when quinoxaline bridged, as in 1-7, and at all available temperatures when pyrazine bridged, as in 13. The R and B groups of 1-7 can be varied to control solubility and cavity size without greatly affecting the vase-kite structures. When the 2-position of resorcinol is occupied by a methyl, an ethyl, or a bromine, as in 14-17, only the kite conformation is observed at all available temperatures. When the 2-position is hydrogen and the system is quinoxaline, only the kite conformer is observed at temperatures below -50-degrees-C. When the 2-position is CH3, the kite conformer equilibrates with its dimer. When the 2-position is CH3CH2, as in 17, the kite conformer does not form a dimer. The kite C2v structures under pseudorotation and also dimerize when they contain 2-methylresorcinyl groups to give dimers of D2d symmetry. In some systems, these processes could be differentiated by use of variable-temperature H-1 NMR spectra.
• TUNSTAD, LINDA M.;TUCKER, JOHN A.;DALCANALE, ENRICO;WEISER, JURGEN;BRYANT+, J. ORG. CHEM., 54,(1989) N, C. 1305-1312
  作者：TUNSTAD, LINDA M.、TUCKER, JOHN A.、DALCANALE, ENRICO、WEISER, JURGEN、BRYANT+

  DOI：——

  日期：——