macrocycle 2 | 1155917-93-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: macrocycle 2
• 英文别名: cyclo[4Abz-4Abz-4Abz]；2,8,14-triazatetracyclo[14.2.2.24,7.210,13]tetracosa-1(19),4,6,10(22),11,13(21),16(20),17,23-nonaene-3,9,15-trione
• CAS: 1155917-93-3
• 化学式: C₂₁H₁₅N₃O₃
• 分子量: 357.368
• InChiKey: SYNYQENQYPCXMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  macrocycle 1a 在 三异丙基硅烷 、 三氟乙酸 作用下， 以100%的产率得到macrocycle 2
  参考文献：
  名称：

  对氨基苯甲酸衍生的苯三甲酰胺大环的简便合成

  摘要：

  以区域特异性方式在外围功能化的大环化合物的合成被认为是具有挑战性的。这封信描述了由对氨基苯甲酸衍生的N-烷基化苯三甲酰胺大环化合物的六步合成，该过程通过Fmoc保护的单体的迭代偶联和所得线性折叠子的环化反应来进行。

  DOI：

  10.1016/j.tetlet.2009.12.137

文献信息

• An ‘impossible’ macrocyclisation using conformation directing protecting groups
  作者：Fred Campbell、Andrew J. Wilson

  DOI：10.1016/j.tetlet.2009.02.186

  日期：2009.5

  A p-benzenetricarboxamide macrocycle linked through secondary cis amides is obtained via cyclisation and subsequent deprotection of a folded linear precursor. Secondary benzamides strongly prefer the trans conformation, therefore this synthesis can be considered 'impossible' without recourse to protecting groups. (C) 2009 Elsevier Ltd. All rights reserved.
• One-Pot Synthesis and AFM Imaging of a Triangular Aramide Macrocycle
  作者：Christof Storz、Michael Badoux、Christopher M. Hauke、Tomáš Šolomek、Angelika Kühnle、Thomas Bally、Andreas F. M. Kilbinger

  DOI：10.1021/ja506646s

  日期：2014.9.17

  Macrocyclizations in exceptionally good yields were observed during the self-condensation of N-benzylated phenyl p-aminobenzoates in the presence of LiHMDS to yield three-membered cyclic aramides that adopt a triangular shape. An ortho-alkyloxy side chain on the N-benzyl protecting group is necessary for the macrocyclization to occur. Linear polymers are formed exclusively in the absence of this Li-chelating group. A model that explains the lack of formation of other cyclic congeners and the demand for an N-(o-alkoxybenzyl) protecting group is provided on the basis of DFT calculations. High-resolution AFM imaging of the prepared molecular triangles on a calcite(10.4) surface shows individual molecules arranged in groups of four due to strong surface templating effects and hydrogen bonding between the molecular triangles.