(R)-α-(1-naphthyl)ethylamine perchlorate salt | 82456-17-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-α-(1-naphthyl)ethylamine perchlorate salt
• 英文别名: 1-(1-naphthyl)ethylamine hydrogen perchlorate；(R)-1-(1-naphthyl)ethylamine hydrogen perchlorate；[(1R)-1-naphthalen-1-ylethyl]azanium;perchlorate
• CAS: 82456-17-5
• 化学式: C₁₂H₁₃N*ClHO₄
• 分子量: 271.7
• InChiKey: QXAAJXYQCJKEPO-SBSPUUFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.61
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-2-methyl-3,6,9,12-tetraoxa-15,22-diazatricyclo[13.7.0.016,21]docosa-1(22),16,18,20-tetraene 、 (R)-α-(1-naphthyl)ethylamine perchlorate salt 以 乙腈 为溶剂， 生成 perchloric acid compound with (R)-1-(naphthalen-1-yl)ethan-1-amine and (S)-1-methyl-3,4,6,7,9,10,12,13-octahydro-1H-benzo[4,5]imidazo[2,1-l][1,4,7,10]tetraoxa[13]azacyclopentadecine (1:1:1)
  参考文献：
  名称：

  Chiral benzimidazole-derived mono azacrowns: synthesis and enantiomer recognition studies with chiral amines and their ammonium salts

  摘要：

  Benzimidazole fused chiral mono aza-15-crown-5 2, was obtained in a single step from (S)-(-)-2-(alpha-hydroxyethyl) benzimidazole 1. This new class of aza-crown has a unique structure with the chiral unit being held in a stable conformation due to adjacent benzimidazole ring contributing to its stereodiscrimination ability. The interactions between the host aza-crown and enantiomerically pure amine guests in ionic and neutral forms exhibited the enantio-discrimination ability. The preliminary evaluation of the chiral sensing was monitored using H-1 NMR and circular dichroism (CD) analysis of the complexes at their molar equivalence. The binding parameters were determined using electronic absorption spectroscopy. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.04.021
• 作为产物：
  描述：

  (+/-)-<α-(1-naphthyl)ethyl>ammonium perchlorate 生成 (R)-α-(1-naphthyl)ethylamine perchlorate salt
  参考文献：
  名称：

  Huszthy, P.; Bradshaw, J. S.; Bordunov, A. V., ACH - Models in Chemistry, 1994, vol. 131, # 3-4, p. 445 - 454

  摘要：

  DOI：

文献信息

• Synthesis and p<i>K</i> _a determination of new enantiopure dimethyl-substituted acridino-crown ethers containing a carboxyl group: Useful candidates for enantiomeric recognition studies
  作者：Tamás Németh、Gergő Dargó、József Levente Petró、Zsófia Petrik、Sándor Lévai、Balázs Krámos、Zoltán Béni、József Nagy、György Tibor Balogh、Péter Huszthy、Tünde Tóth

  DOI：10.1002/chir.22721

  日期：2017.9

  New enantiopure dimethyl‐substituted acridino‐18‐crown‐6 and acridino‐21‐crown‐7 ethers containing a carboxyl group at position 9 of the acridine ring [(S,S)‐8, (S,S)‐9, (R,R)‐10] were synthesized. The pKa values of the new crown ethers [(S,S)‐8, (S,S)‐9, (R,R)‐10] and of an earlier reported macrocycle [(R,R)‐2] were determined by UV‐pH titrations. Crown ether (S,S)‐8 was attached to silica gel by

  在对cr啶环[[ S，S）-8，（S，S）-9，（R，R）-10 ]合成。新冠醚[（S，S）‐8，（S，S）‐9，（R，R）‐10 ]和较早报告的大环化合物[（R，R）‐2 ]的p K a值用UV-pH滴定法测定。冠醚（S，S）-8通过共价键连接到硅胶上，并通过高效液相色谱（HPLC）研究了新制备的手性固定相[（S，S）-CSP- 12 ]的对映体分离能力。观察到手性偏爱，对1-NEA的对映异构体实现了最佳分离。配体（S，S）-9和（R，R）-10是质子化伯胺，氨基酸及其衍生物的对映异构体的对映选择性传感器和选择分子的前体。
• Pyridino-18-crown-6 ether type chemosensors containing a benzothiazole fluorophore unit: Synthesis and enantiomeric recognition studies
  作者：Dávid Pál、Ildikó Móczár、Balázs Szemenyei、Dániel Marczona、Ivett Kocsis、Gergely Prikler、Panna Vezse、Péter Baranyai、Péter Huszthy

  DOI：10.1016/j.tet.2019.04.024

  日期：2019.5

  new fluorescent enantiopure pyridino-18-crown-6 ethers containing a benzothiazole unit were prepared, and the enantiomeric discrimination of these sensor molecules toward the hydrogen perchlorate salts of 1-phenylethylamine, 1-(1-naphthyl)ethylamine, phenylglycine methyl ester and phenylalanine methyl ester was studied in acetonitrile by fluorescence spectroscopy. The ligands revealed appreciable or

  制备了三种新的含苯并噻唑单元的荧光对映体纯吡啶基-18-冠-6醚，并将这些传感器分子对1-苯基乙胺，1-（1-萘基）乙胺，苯基甘氨酸甲酯和通过荧光光谱法研究了乙腈中的苯丙氨酸甲酯。所述配体对1-苯基乙胺，1-（1-萘基）乙胺和苯基甘氨酸甲酯的高氯酸氢盐的对映异构体显示出适度或适度的选择性。
• When crown ethers finally click: novel, click-assembled, fluorescent enantiopure pyridino-crown ether-based chemosensors <b>–</b> and an <i>N</i>-2-aryl-1,2,3-triazole containing one
  作者：Balázs Szemenyei、Mira Malmosi、Dávid Pál、Péter Baranyai、László Drahos、Ildikó Móczár、Péter Huszthy

  DOI：10.1039/d1nj04173h

  日期：——

  novel, click-assembled fluorescent pyridino-18-crown-6 ethers have been synthesized for enantiomeric sensing. We also prepared new azide- and ethynyl-substituted pyridino-18-crown-6 ethers as their precursors, which open the way for further interesting applications using click chemistry. An optically active pyridino-18-crown-6 ether containing an N-2-aryl-1,2,3-triazole type fluorophore unit was also

  已经合成了三种新颖的、点击组装的荧光 pyridino-18-crown-6 醚用于对映体传感。我们还制备了新的叠氮化物和乙炔基取代的 pyridino-18-crown-6 醚作为它们的前体，这为使用点击化学进一步有趣的应用开辟了道路。还通过后三唑芳基化合成了含有N -2-芳基-1,2,3-三唑型荧光团单元的旋光性吡啶基-18-冠-6 醚。研究了这四种荧光传感器分子的光学特性以及它们对 1-苯乙胺、1-（1-萘基）乙胺、苯甘氨酸甲酯和苯丙氨酸甲酯在乙腈中的高氯酸氢盐的对映体识别能力。
• Synthesis and Enantiomeric Recognition Studies of Optically Active Pyridino-Crown Ethers Containing an Anthracene Fluorophore Unit
  作者：Balázs Szemenyei、Ildikó Móczár、Dávid Pál、Ivett Kocsis、Péter Baranyai、Péter Huszthy

  DOI：10.1002/chir.22614

  日期：2016.7

  Novel enantiopure pyridino‐18‐crown‐6 ether‐based sensor molecules containing an anthracene fluorophore unit were synthesized. Their enantiomeric recognition abilities toward the enantiomers of 1‐phenylethylamine hydrogen perchlorate (PhEt), 1‐(1‐naphthyl)ethylamine hydrogen perchlorate (NapEt), phenylglycine methyl ester hydrogen perchlorate (PhgOMe), and phenylalanine methyl ester hydrogen perchlorate

  合成了含有蒽荧光团的新型对映体纯的吡啶基-18-冠-6醚基传感器分子。它们对1-苯乙胺高氯酸氢盐（PhEt），1-（1-萘基）乙胺高氯酸氢盐（NapEt），苯甘氨酸甲酯高氯酸氢盐（PhgOMe）和苯丙氨酸甲酯高氯酸氢盐（PheOMe）的对映体识别能力为。使用荧光光谱法在乙腈中检测。传感器分子对NapEt，PhEt和PhgOMe的对映异构体显示出可观的对映异构体识别。发现在大环上含有异丁基的冠醚和NapEt的对映异构体中，对映选择性最高。手性28：562–568，2016。©2016 Wiley Periodicals，Inc.
• Structural characterization of the crystalline diastereomeric complexes of enantiopure dimethylacridino-18-crown-6 ether and the enantiomers of 1-(1-naphthyl)ethylamine hydrogen perchlorate
  作者：Tünde Tóth、Tamás Németh、Ibolya Leveles、Beáta G. Vértessy、Péter Huszthy

  DOI：10.1007/s11224-016-0818-6

  日期：2017.4

  This paper describes the X-ray crystal structure of the diastereomeric complexes formed by enantiopure dimethyl-substituted acridino-18-crown-6 ether (R,R)-1 and the enantiomers of 1-(1-naphthyl)ethylammonium perchlorate. We found that the heterochiral complex (R,R)-1–(S)-1-NEA is more stable than the homochiral one (R,R)-1–(R)-1-NEA. In the case of the heterochiral complex, the X-ray studies revealed

  本文描述了由对映体纯二甲基取代的吖啶基-18-冠-6 醚 (R,R)-1 和 1-(1-萘基) 乙基高氯酸铵的对映体形成的非对映体配合物的 X 射线晶体结构。我们发现异手性复合物 (R,R)-1–(S)-1-NEA 比同手性复合物 (R,R)-1–(R)-1-NEA 更稳定。在异手性配合物的情况下，X 射线研究揭示了萘基单元和吖啶部分之间强烈的分子间 π-π 相互作用。然而，在同手性配合物的情况下，没有发现 π-π 相互作用。我们认为 π-π 相互作用的存在或不存在以及非对映异构体中空间排斥的差异是对映体区分的原因。