3,5,13,15,21,22-hexaazatricyclo[15.3.1.1^7,11]docosa-1(21),7(22),8,10,-17,19-hexaene-4,14-dione | 1263199-86-5

• 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: 3,5,13,15,21,22-hexaazatricyclo[15.3.1.1^7,11]docosa-1(21),7(22),8,10,-17,19-hexaene-4,14-dione
• 英文别名: 3,5,13,15,21,22-Hexazatricyclo[15.3.1.17,11]docosa-1(21),7(22),8,10,17,19-hexaene-4,14-dione；3,5,13,15,21,22-hexazatricyclo[15.3.1.17,11]docosa-1(21),7(22),8,10,17,19-hexaene-4,14-dione
• CAS: 1263199-86-5
• 化学式: C₁₆H₁₈N₆O₂
• 分子量: 326.358
• InChiKey: DXXMEXQNBOIWLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5,13,15,21,22-hexaazatricyclo[15.3.1.1^7,11]docosa-1(21),7(22),8,10,-17,19-hexaene-4,14-dione 、 苯酚 以 正庚烷 为溶剂， 生成
  参考文献：
  名称：

  Absorption of Hydrogen Bond Donors by Pyridyl Bis-Urea Crystals

  摘要：

  A one-dimensional crystalline solid built from pillars of self-assembled bis-urea pyridyl macrocycles affords a close packed structure with no pores. These organic pillars contain unsatisfied urea oxygen lone pairs that can be used to drive the absorption of alcohols including trifluoroethanol, phenol, pentafluorophenol, and ethylene glycol to give well-ordered host:guest complexes with repeatable stoichiometry. The driving force for reversible solid transitions appears to be the formation of hydrogen bonds between the guest and an unsatisfied hydrogen bond acceptor, which is a lone pair of the urea oxygen. Halogen bonding with the electrophilic iodide in pentafluoroiodobenzene can also drive absorption by the host to give a well-ordered host:guest complex. These results suggest that the organic solid-state is surprisingly dynamic and may have potential applications for sorbents.

  DOI：

  10.1021/cm302658q
• 作为产物：
  描述：

  11,23-Ditert-butyl-1,9,11,13,21,23,26,28-octazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-3(28),4,6,15,17,19(26)-hexaene-25,27-dione 以 甲醇 、 水 、 二乙醇胺 为溶剂， 反应 24.0h， 以93%的产率得到3,5,13,15,21,22-hexaazatricyclo[15.3.1.1^7,11]docosa-1(21),7(22),8,10,-17,19-hexaene-4,14-dione
  参考文献：
  名称：

  Guest induced transformations of assembled pyridyl bis-urea macrocycles

  摘要：

  没有孔洞的吡啶大环组装成紧密堆积的柱状结构，但仍能吸附氢气、二氧化碳和碘等客体。

  DOI：

  10.1039/c0cc01952f

文献信息

• Temperature-induced pseudopolymorphism of molecular salts from a pyridyl bis-urea macrocycle and naphthalene-1,5-disulfonic acid
  作者：Bozumeh Som、Jessica R. Shue、Mark D. Smith、Linda S. Shimizu

  DOI：10.1107/s2053229617017600

  日期：2018.1.1

  Molecular salts, often observed as cocrystals, play an important role in the fields of pharmaceutics and materials science, where salt formation is used to tune the properties of active pharmaceutical ingredients (APIs) and improve the stability of solid‐state materials. Salt formation via a proton‐transfer reaction typically alters hydrogen‐bonding motifs and influences supramolecular assembly patterns

  分子盐通常作为共晶体被观察到，在药学和材料科学领域起着重要作用，其中盐的形成用于调节活性药物成分（API）的性能并提高固态材料的稳定性。通过质子转移反应形成盐通常会改变氢键基序并影响超分子组装模式。我们在这里报告由吡啶基双脲大环化合物3,5,13,​​15,21,22-六氮杂三环[15.3.1.1 7,11 ] docosa -1（21），7（22），8,10形成的分子盐，17,19-己烯-4,14-二酮（1）和萘-1,5-二磺酸（H 2 NDS）作为两个盐共晶溶剂化物，即4,14-dioxo-3,5,13， 15,21,22-六氮杂三环[15.3.1.1 7,11] docosa‐1（21），7（22），8,10,17,19‐己烯‐21,22‐萘萘‐1,5-二磺酸盐二甲亚砜二溶剂化物，C 16 H 20 N 6 O 2 2 + · C 10 H 6 O 6 S 2 2- ·2C 2 H 6
• Pillars of assembled pyridyl bis-urea macrocycles: a robust synthon to organize diiodotetrafluorobenzenes
  作者：Bozumeh Som、Sahan R. Salpage、Juno Son、Bing Gu、Stavros G. Karakalos、Mark D. Smith、Linda S. Shimizu

  DOI：10.1039/c6ce02392d

  日期：——

  this synthon with a series of activated halogen bond donors, the regio-isomers of diiodotetrafluorobenzenes, which vary the relative orientation of the halogen bond formers. Irrespective of the initial stoichiometry, each donor only formed one type of co-crystal with 1. In each case, similar strong pillars of assembled 1 were observed that organize the donors through the CO⋯I interaction, which were

  柱状组装的吡啶基双-脲大环化合物1提供了强大的一维超分子合成子，可构建分层组装。这些一维支柱包含碱性氧孤对形式的对位对称受体。在本文中，我们用一系列活化的卤素键供体（二碘四氟苯的区域异构体）探测了这种合成子，这改变了卤素键形成体的相对取向。不论初始化学计量如何，每个供体仅与1形成一种共晶。在每种情况下，都观察到组装件1的类似坚固支柱，它们通过C来组织捐助者O⋯I相互作用显着短于所涉原子的范德华半径之和，并且是中性有机分子中报告的最短的相互作用。X射线光电子能谱的特征核能级变化强烈表明卤素键相互作用的形成。这些研究表明，这种合成子可以正交利用氢键和卤素键来构建复杂的结构。
• Guest induced transformations of assembled pyridyl bis-urea macrocycles
  作者：Kinkini Roy、Chun Wang、Mark D. Smith、Mahender B. Dewal、Arief C. Wibowo、Julius C. Brown、Shuguo Ma、Linda S. Shimizu

  DOI：10.1039/c0cc01952f

  日期：——

  Pyridine macrocycles with no cavities assembled into close packed columns yet absorbed guests including hydrogen, carbon dioxide, and iodine.

  没有孔洞的吡啶大环组装成紧密堆积的柱状结构，但仍能吸附氢气、二氧化碳和碘等客体。
• Absorption of Hydrogen Bond Donors by Pyridyl <i>Bis</i>-Urea Crystals
  作者：Kinkini Roy、Arief C. Wibowo、Perry J. Pellechia、Shuguo Ma、Michael F. Geer、Linda S. Shimizu

  DOI：10.1021/cm302658q

  日期：2012.12.21

  A one-dimensional crystalline solid built from pillars of self-assembled bis-urea pyridyl macrocycles affords a close packed structure with no pores. These organic pillars contain unsatisfied urea oxygen lone pairs that can be used to drive the absorption of alcohols including trifluoroethanol, phenol, pentafluorophenol, and ethylene glycol to give well-ordered host:guest complexes with repeatable stoichiometry. The driving force for reversible solid transitions appears to be the formation of hydrogen bonds between the guest and an unsatisfied hydrogen bond acceptor, which is a lone pair of the urea oxygen. Halogen bonding with the electrophilic iodide in pentafluoroiodobenzene can also drive absorption by the host to give a well-ordered host:guest complex. These results suggest that the organic solid-state is surprisingly dynamic and may have potential applications for sorbents.