(2R,3R,12R,13R,22R,23R)-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 | 302792-00-3

• 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: (2R,3R,12R,13R,22R,23R)-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: 302792-00-3
• 化学式: C₄₂H₄₈N₆
• 分子量: 636.883
• InChiKey: AUGUBIDKXUONSG-BSBWAFOKSA-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：

  (2R,3R,12R,13R,22R,23R)-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 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 (2R,3R,12R,13R,22R,23R)-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,5H,10H,11H,12H,13H,14H,15H,20H,21H,22H,23H,24H,25H,30H)-octadecahydro-(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：

  对苯二甲醛 、 (1R,2R)-1,2-diaminocyclohexane 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (2R,3R,12R,13R,22R,23R)-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：

  混合成分产生的一致的超分子组装-手性含氧的Trianglimines的自分选和固溶体†

  摘要：

  含氧或甲氧基的对苯二醛与光学纯的邻位二胺的[3 + 3]环缩合可提供三角形大环，其结构和对称性取决于醛底物的结构。六氧合的Trianglimine的形成具有很高的立体选择性：也就是说，使用外消旋二胺会产生外消旋的同手性三角大环化合物，每个环在所有立体成因中心均具有相同的绝对构型。然而，当非，单和双氧合二醛的混合物与光学纯的二胺进行环缩合反应时​​，没有观察到自分选。在晶体中，各种含氧的Trianglimines始终如一地组装成手性柱状聚集体，并形成两组分或三组分固溶体。这些组件中的某些组件具有列内和/或列间包含特性。虽然三氧合的Trianglimine结晶为分子异构体的固溶体，但由各种氧合的醛亚基组成的均匀手性大环的混合物提供了一种三元固溶体，该三元固溶体缺乏任何溶剂分子。对于外消旋的trianglimine，超分子柱状组装体的形成是通过对映选择性自我识别来完成的。

  DOI：

  10.1039/c8ce01044g

文献信息

• Trianglamines—Readily Prepared, Conformationally Flexible Inclusion-Forming Chiral Hexamines
  作者：Jacek Gawronski、Krystyna Gawronska、Jakub Grajewski、Marcin Kwit、Agnieszka Plutecka、Urszula Rychlewska

  DOI：10.1002/chem.200500887

  日期：2006.2.8

  Trianglamines, macrocyclic heteraphanes, were readily synthesised through a [3+3] cyclocondensation of (R,R)-1,2-diaminocyclohexane with terephthalaldehyde, followed by NaBH4 reduction and N-alkylation. The macrocyclic ring shows a remarkable ability to change its conformation, as a consequence of rotation about the C-N bonds or nitrogen inversion due to protonation or N-alkylation, as revealed by

  通过（R，R）-1,2-二氨基环己烷与对苯二醛的[3 + 3]环缩合，然后NaBH4还原和N-烷基化，可以轻松合成大环杂芳基三苯胺。大圆环显示出显着的改变其构象的能力，这是由于绕圆二色光谱，计算模型和X射线衍射分析所揭示的，由于绕CN键旋转或由于质子化或N-烷基化而引起的氮反转，导致其构象改变的能力。Trianglamine大环化合物的柔韧性使各种客体分子易于容纳，从而形成具有高度互穿结构的晶体包合物。
• Microwave assisted cyclocondensation of dialdehydes with chiral diamines forming calixsalen type macrocycles
  作者：Sankareswaran Srimurugan、Balasubramanian Viswanathan、Thirukkallam Kanthadai Varadarajan、Babu Varghese

  DOI：10.1016/j.tetlet.2005.03.089

  日期：2005.5

  Microwave irradiation of various dialdellydes and chiral diamines afforded chiral macrocyclic imines in moderate to good yields. Linked dialdehydes predominantly form [2+2] macrocycles whereas dialdehydes without linkers yield [3+3] macrocycles. This is the first report of template-free synthesis of calixsalen-type macrocycles formed in shorter reaction times under micro vave conditions. In all the reactions, the salts of chiral diamines were used in contrast to the free diamines normally employed. (c) 2005 Elsevier Ltd. All rights reserved.
• Designing Large Triangular Chiral Macrocycles:  Efficient [3 + 3] Diamine−Dialdehyde Condensations Based on Conformational Bias
  作者：J. Gawroński、H. Kołbon、M. Kwit、A. Katrusiak

  DOI：10.1021/jo000623v

  日期：2000.9.1

  Triangular 30- and 27-membered hexaiminomacrocycles 4 and 5 of D-3 and C-3 symmetry, respectively, are readily obtained by unprecedented [3 + 3] cyclocondensation of (R,R)-1,2-diaminocyclohexane with, accordingly, terephthalaldehyde and isophthalaldehyde. The course of the reaction, leading to macrocyclization, is governed by conformational constraints imposed on the structural components of the intermediate products, as shown by molecular modeling. X-ray analysis of cocrystal 4 . AcOEt revealed that the macrocycle symmetry significantly departs from ideal D3 symmetry due to crystal environment. Cyclic hexaamines 6 and 7 were prepared by sodium borohydride reduction of 4 and 5, respectively.
• (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.