(2S,3S,12S,13S,22S,23S)-1,4,11,14,21,24-hexaaza(2,3:12,13:22,23)-tributano-(6,9:16,19:26,29)-trietheno-(2H,3H,12H,13H,22H,23H)-hexahydro-(30)-annulene | 342905-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: (2S,3S,12S,13S,22S,23S)-1,4,11,14,21,24-hexaaza(2,3:12,13:22,23)-tributano-(6,9:16,19:26,29)-trietheno-(2H,3H,12H,13H,22H,23H)-hexahydro-(30)-annulene
• CAS: 342905-79-7
• 化学式: C₄₂H₄₈N₆
• 分子量: 636.883
• InChiKey: AUGUBIDKXUONSG-XRITYDAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.55
• 重原子数：
  48.0
• 可旋转键数：
  0.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  74.16
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,12S,13S,22S,23S)-1,4,11,14,21,24-hexaaza(2,3:12,13:22,23)-tributano-(6,9:16,19:26,29)-trietheno-(2H,3H,12H,13H,22H,23H)-hexahydro-(30)-annulene 在 硼氘化钠 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 (2S,3S,12S,13S,22S,23S)-1,4,11,14,21,24-hexaaza-(2,3:12,13:22,23)-tributano-(6,9:16,19:26,29)-trietheno-1H,2H,3H,4H,11H,12H,13H,14H,21H,22H,23H,24H-dodecahydro-5,10,15,20,25,30-hexadeuterio-(30)-annulene
  参考文献：
  名称：

  Synthesis, self-association and chiroselectivity of isotopically labeled trianglamine macrocycles in the ion trap mass spectrometer

  摘要：

  该研究描述了在离子阱电喷雾质谱条件下手性同位素标记的三苯胺大环的合成和自结合过程。在自结合过程中观察到了适度的非对映选择性，为研究气相中的手性自结合提供了一个合成模型系统。在气相中观察到了第一个完全通过芳香-芳香相互作用结合的非共价结合二聚体。通过扩散核磁共振光谱观察到了溶液中自结合的证据。Copyright © 2007 John Wiley & Sons, Ltd. All Rights Reserved.

  DOI：

  10.1002/jlcr.1449
• 作为产物：
  描述：

  (1S,2S)-(+)-1,2-环己二胺 、 对苯二甲醛 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到(2S,3S,12S,13S,22S,23S)-1,4,11,14,21,24-hexaaza(2,3:12,13:22,23)-tributano-(6,9:16,19:26,29)-trietheno-(2H,3H,12H,13H,22H,23H)-hexahydro-(30)-annulene
  参考文献：
  名称：

  Synthesis, self-association and chiroselectivity of isotopically labeled trianglamine macrocycles in the ion trap mass spectrometer

  摘要：

  该研究描述了在离子阱电喷雾质谱条件下手性同位素标记的三苯胺大环的合成和自结合过程。在自结合过程中观察到了适度的非对映选择性，为研究气相中的手性自结合提供了一个合成模型系统。在气相中观察到了第一个完全通过芳香-芳香相互作用结合的非共价结合二聚体。通过扩散核磁共振光谱观察到了溶液中自结合的证据。Copyright © 2007 John Wiley & Sons, Ltd. All Rights Reserved.

  DOI：

  10.1002/jlcr.1449

文献信息

• (3+3)-Cyclocondensation of the enantiopure and racemic forms of trans-1,2-diaminocyclohexane with terephthaldehyde. Formation of diastereomeric molecular triangles and their stereoselective solid-state stacking into microporous chiral columns
  作者：Martin Chadim、Miloš Buděšı́nský、Jana Hodačová、Jiřı́ Závada、Peter C. Junk

  DOI：10.1016/s0957-4166(00)00494-8

  日期：2001.2

  The non-templated reaction of both the homochiral as well as the racemic form of trans-1,2-diaminocyclohexane with terephthaldehyde affords (3+3)-cyclocondensed molecular triangles in practically quantitative yields. The configuration of the diastereomeric products resulting in the individual reactions has been determined by H-1 and C-13 NMR spectroscopy. Unambiguous proof has been obtained by X-ray crystal structure analysis of both alternative diastereomers, revealing also a stereoselective stacking of the triangles into microporous chiral columns. (C) 2001 Elsevier Science Ltd. All rights reserved.
• The application of quasi-enantiomeric trianglamine macrocycles as chiral probes for anion recognition in ion trap ESI mass spectrometry
  作者：Nikolai Kuhnert、David Marsh、Daniel C. Nicolau

  DOI：10.1016/j.tetasy.2007.07.011

  日期：2007.7

  This paper reports the synthesis and application of quasi-enantiomeric trianglamine macrocycles for chiral analysis using ion trap ESI mass spectrometry. The quasi-enantiomeric macrocycles were shown to display chiroselection towards a series of enantiomerically pure carboxylic acids and therefore act as chiral probes for anions in the gas phase and in solution. (c) 2007 Elsevier Ltd. All rights reserved.