6,13,20,27,34-Pentabenzyl-3,10,17,24,31-pentahydroxy-2,6,9,13,16,20,23,27,30,34-decazahexacyclo[30.3.1.14,8.111,15.118,22.125,29]tetraconta-1(35),2,4,7,9,11,14,16,18,21,23,25,28,30,32-pentadecaene-36,37,38,39,40-pentone | 1325297-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6,13,20,27,34-Pentabenzyl-3,10,17,24,31-pentahydroxy-2,6,9,13,16,20,23,27,30,34-decazahexacyclo[30.3.1.14,8.111,15.118,22.125,29]tetraconta-1(35),2,4,7,9,11,14,16,18,21,23,25,28,30,32-pentadecaene-36,37,38,39,40-pentone
• 英文别名: 6,13,20,27,34-pentabenzyl-3,10,17,24,31-pentahydroxy-2,6,9,13,16,20,23,27,30,34-decazahexacyclo[30.3.1.14,8.111,15.118,22.125,29]tetraconta-1(35),2,4,7,9,11,14,16,18,21,23,25,28,30,32-pentadecaene-36,37,38,39,40-pentone
• CAS: 1325297-09-3
• 化学式: C₆₅H₅₀N₁₀O₁₀
• 分子量: 1131.17
• InChiKey: XYNWSSWDFHQVNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  85
• 可旋转键数：
  10
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  265
• 氢给体数：
  5
• 氢受体数：
  20

反应信息

• 作为产物：
  描述：

  4-氧代-1,4-二氢-3,5-吡啶二羧酸二乙酯 在 N-甲基吗啉 、 硫酸 、 氯甲酸乙酯 、 potassium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 88.92h， 生成 6,13,20,27,34-Pentabenzyl-3,10,17,24,31-pentahydroxy-2,6,9,13,16,20,23,27,30,34-decazahexacyclo[30.3.1.14,8.111,15.118,22.125,29]tetraconta-1(35),2,4,7,9,11,14,16,18,21,23,25,28,30,32-pentadecaene-36,37,38,39,40-pentone
  参考文献：
  名称：

  BOP介导的C5对称大环吡啶酮五聚体的一锅合成。

  摘要：

  我们在这里首次报告由内部放置的分子内H键促进和引导的BOP介导的一锅大环化，以允许高度选择性地形成五残基阳离子结合大环。

  DOI：

  10.1039/c1cc14377h

文献信息

• Computation-guided improved one-pot synthesis of macrocyclic cation-binding aromatic pyridone pentamers
  作者：Vicky Ziman Zeng、Haibin Su、Tianhu Li

  DOI：10.1039/c6ob01841f

  日期：——

  By using polar DMF to relax the H-bonded rigid backbone and to lower the energetic penalty associated with the sterically-crowded environment, the yields for BOP-mediated one-pot synthesis of pentameric macrocycles can be improved from 10–25% as obtained in CH2Cl2 to 13–47% when 15% DMF in CH2Cl2 was used as the reaction medium.

  通过使用极性DMF松弛H键合的刚性主链并降低与空间拥挤环境相关的能量损失，BOP介导的一锅合成五聚体大环化合物的收率可以从10-25％的情况下提高。当将CH 2 Cl 2中的15％DMF用作反应介质时，CH 2 Cl 2的含量为13-47％。
• Five-Fold-Symmetric Macrocyclic Aromatic Pentamers: High-Affinity Cation Recognition, Ion-Pair-Induced Columnar Stacking, and Nanofibrillation
  作者：Changliang Ren、Victor Maurizot、Huaiqing Zhao、Jie Shen、Feng Zhou、Wei Qiang Ong、Zhiyun Du、Kun Zhang、Haibin Su、Huaqiang Zeng

  DOI：10.1021/ja206457b

  日期：2011.9.7

  Described in this study is a conceptually new class of five-fold-symmetric cavity-containing planar pentameric macrocycles with their interior decorated by five convergently aligned, properly spaced carbonyl oxygen atoms. These cation-binding oxygens enclose a hydrophilic lumen of 2.85 angstrom in radius and thus display high-affinity binding toward alkali metal cations, and possibly many other cations, too. Arising from their high-affinity recognition of metal ions, these planar macrocycles form cation- or ion-pair-induced one-dimensional columnar aggregates, and subsequently fascinating fibrillation results.
• BOP-mediated one-pot synthesis of C5-symmetric macrocyclic pyridone pentamers
  作者：Zhiyun Du、Changliang Ren、Ruijuan Ye、Jie Shen、Victor Maurizot、Yujin Lu、Jian Wang、Huaqiang Zeng

  DOI：10.1039/c1cc14377h

  日期：——

  We report here, for the first time, the BOP-mediated one-pot macrocyclization that is facilitated and guided by internally placed intramolecular H-bonds to allow for the highly selective formation of five-residue cation-binding macrocycles.

  我们在这里首次报告由内部放置的分子内H键促进和引导的BOP介导的一锅大环化，以允许高度选择性地形成五残基阳离子结合大环。