5,17-bis-(chloromethyl)-11,23-di-tert-butylcalix<4>arene-25,26,27,28-tetrol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5,17-bis-(chloromethyl)-11,23-di-tert-butylcalix<4>arene-25,26,27,28-tetrol
• 英文别名: 5,17-bis(chloromethyl)-11,23-di-tert-butylcalix[4]aren；5,17-bis(chloromethyl)-11,23-bis(p-tert-butyl)-25,26,27,28-tetrahydroxycalix[4]arene；5,17-Ditert-butyl-11,23-bis(chloromethyl)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
• 化学式: C₃₈H₄₂Cl₂O₄
• 分子量: 633.655
• InChiKey: VABGXYKLQUTFRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  44
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  5,17-bis-(chloromethyl)-11,23-di-tert-butylcalix<4>arene-25,26,27,28-tetrol 在 三乙胺 、 三氟乙酸 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 (2S,4R)-4-[[11,23-ditert-butyl-17-[[[(3R,5S)-5-carboxypyrrolidin-3-yl]amino]methyl]-25,26,27,28-tetrahydroxy-5-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-dodecaenyl]methylamino]pyrrolidine-2-carboxylic acid
  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
• 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 、 四氯化锡 、 甲苯 、 sodium hydroxide 作用下， 以 乙醇 、 氯仿 、 重水 为溶剂， 反应 14.0h， 生成 5,17-bis-(chloromethyl)-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

• Synthesis and Reactivity of Calix[4]arene-Based Copper Complexes¹
  作者：Dejian Xie、C. David Gutsche

  DOI：10.1021/jo981038l

  日期：1998.12.1

  The interaction of copper and oxygen with calix[4]arenes carrying one pr two chelating moieties on the upper rim has been investigated. The chelating moieties include pyrazolyethyl and pyridylethyl functions attached to an amino nitrogen separated from the calixarene rim by one or two methylene groups. The products obtained by treatment of the pyrazole-based calixarenes with Cu(I) and Cu(II) are stable to oxidation (by O-2) and reduction (by MeOH), respectively. Those produced by treatment of the pyridine-based calixarenes with Cu(I), however, are more reactive and undergo intramolecular oxidation at the benzylic carbon of the chelate-containing side chain. Putative pathways for the decomposition of the dicopper-dioxygen complexes are discussed.
• Transportation of Poorly Soluble Drug Molecules from the Organic Phase to the Aqueous Phase by Using Phosphorylated Calixarenes
  作者：Mevlüt Bayrakcı、Şeref Ertul、Mustafa Yilmaz

  DOI：10.1021/je2004319

  日期：2011.12.8

  This study is the first report on the extraction of poorly soluble drug molecules such as nifedipine, niclosamide, and furosemide from the organic phase to the aqueous phase by water-soluble p-phosphonate calix[n]arene receptors via a liquid-liquid phase extraction process. These water-soluble calixarene derivatives were easily obtained from the reaction between their corresponding chloromethylated derivatives and trimethyl phosphite. From the liquid-liquid phase extraction studies, it was observed that the size of the p-phosphonate calix[n]arenes changed the extraction percentage of selected drug molecules.
• Upper rim-functionalized calix[4]arene-based l-proline as organocatalyst for direct asymmetric aldol reactions in water and organic media
  作者：Arzu Uyanik、Mevlut Bayrakci、Serkan Eymur、Mustafa Yilmaz

  DOI：10.1016/j.tet.2014.10.063

  日期：2014.12

  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.