4-nitro-N-(4,11,17,24-tetraoxo-2,26-dioxa-5,10,18,23,32-pentazatricyclo[25.3.1.112,16]dotriaconta-1(31),12(32),13,15,27,29-hexaen-31-yl)benzamide | 1415263-09-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 4-nitro-N-(4,11,17,24-tetraoxo-2,26-dioxa-5,10,18,23,32-pentazatricyclo[25.3.1.112,16]dotriaconta-1(31),12(32),13,15,27,29-hexaen-31-yl)benzamide
• CAS: 1415263-09-0
• 化学式: C₃₂H₃₅N₇O₉
• 分子量: 661.671
• InChiKey: OXVWBHAKYZHRLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  48
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  223
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  吡啶-2.6-二羧酸二甲酯 在 盐酸 、 sodium methylate 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 11.92h， 生成 4-nitro-N-(4,11,17,24-tetraoxo-2,26-dioxa-5,10,18,23,32-pentazatricyclo[25.3.1.112,16]dotriaconta-1(31),12(32),13,15,27,29-hexaen-31-yl)benzamide
  参考文献：
  名称：

  A General Method for Synthesis of Unclosed Cryptands via H-Bond Templated Macrocyclization and Subsequent Mild Postfunctionalization

  摘要：

  A practical four-step synthesis of a model 26-membered N-Boc-protected macrocycle, starting from commercially available and inexpensive materials, is reported. The crucial macrocyclization step does not require high-dilution conditions and is completed in a short time (8 h). The high yield of macrocyclization (61%) is achieved owing to templation by intramolecular H-bonds and a chloride anion, which both help to adopt a favorable folded conformation of the open-chain intermediate. Finally, mild, selective, and efficient incorporation of intraannular amide function leading to five diversely functionalized unclosed cryptands (UCs) is described.

  DOI：

  10.1021/acs.orglett.5b02324

文献信息

• Stabilization of Near Identical Hydrogen Bonded Octameric Water Clusters in Crystal Structures of Three Distinct Non-Charged Polyamide Macrocyclic Host Molecules
  作者：Kajetan Dąbrowa、Magdalena Ceborska、Janusz Jurczak

  DOI：10.3390/molecules26092787

  日期：——

  tetrahydrates in the same P-1 space group. Moreover, their crystals exhibit identical hydrogen bond motifs resulting in a stabilization of an almost identical unusual octameric water cluster built from the cyclic tetramer core and four water molecules, attached sequentially in an “up-and-down” manner. Further analysis reveals that, among the series, the structure of host 2 provides the most suitable environment

  在本文中，我们对三种溶解度良好的大环主体分子1a，1b和2的水合物的固态结构进行了比较分析，这些分子包含一个环内酰胺-芳基取代基（lariat臂），该环上固定有一个26元环正常（-NHCOAr，主机1a和1b）或反向（-CONHAr，主机2）。尽管化学结构不同，但这些主体在相同的P中结晶为同构四水合物-1个空间组。此外，它们的晶体表现出相同的氢键基序，从而稳定了由环状四聚体核心和四个水分子（以“上下”方式依次连接）构建的几乎相同的不寻常八聚体水簇。进一步的分析表明，在系列中，主机2的结构为容纳这种类型的水簇提供了最合适的环境。
• “Unclosed Cryptands”: A Point of Departure for Developing Potent Neutral Anion Receptors
  作者：Kajetan Dąbrowa、Marcin Pawlak、Piotr Duszewski、Janusz Jurczak

  DOI：10.1021/ol303065k

  日期：2012.12.21

  Six macrocyclic lariat-type compounds, representing a new class of anion receptors, were synthesized in a simple approach. We identified the optimal macroring size and the position of the hydrogen bond donating center in the lariat arm offering the best affinities toward chloride and carboxylate anions. The anion-binding properties of such systems were investigated by applying H-1 NMR titrations in DMSO/water and methanol/DMSO mixtures.
• A General Method for Synthesis of Unclosed Cryptands via H-Bond Templated Macrocyclization and Subsequent Mild Postfunctionalization
  作者：Kajetan Dabrowa、Patryk Niedbala、Maciej Majdecki、Piotr Duszewski、Janusz Jurczak

  DOI：10.1021/acs.orglett.5b02324

  日期：2015.10.2

  A practical four-step synthesis of a model 26-membered N-Boc-protected macrocycle, starting from commercially available and inexpensive materials, is reported. The crucial macrocyclization step does not require high-dilution conditions and is completed in a short time (8 h). The high yield of macrocyclization (61%) is achieved owing to templation by intramolecular H-bonds and a chloride anion, which both help to adopt a favorable folded conformation of the open-chain intermediate. Finally, mild, selective, and efficient incorporation of intraannular amide function leading to five diversely functionalized unclosed cryptands (UCs) is described.