(4S,14S)-(+)-19-iodo-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1(21),17,19-triene | 1380421-68-0

• 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: (4S,14S)-(+)-19-iodo-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1(21),17,19-triene
• 英文别名: (4S,14S)-19-iodo-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]henicosa-1(20),17(21),18-triene
• CAS: 1380421-68-0
• 化学式: C₁₇H₂₆INO₅
• 分子量: 451.302
• InChiKey: XMYXMAPQVKLMJI-KBPBESRZSA-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：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,14S)-(+)-19-iodo-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1(21),17,19-triene 在 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  含苯并噻唑荧光团的Pyridino-18-crown-6醚型化学传感器：合成和对映体识别研究

  摘要：

  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。

  DOI：

  10.1016/j.tet.2019.04.024
• 作为产物：
  描述：

  (2S,12S)-2,12-dimethyl-4,7,10-trioxatridecane-2,12-diol 在 盐酸 、 palladium on activated charcoal 、 氢气 、 sodium hydride 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 (4S,14S)-(+)-19-iodo-4,14-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]heneicosa-1(21),17,19-triene
  参考文献：
  名称：

  含蒽荧光团单元的旋光吡啶并冠醚的合成和对映体识别研究。

  摘要：

  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.

  DOI：

  10.1002/chir.22614

文献信息

• 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。
• Preparation of pyridino-crown ether-based new chiral stationary phases and preliminary studies on their enantiomer separating ability for chiral protonated primary aralkylamines
  作者：József Kupai、Sándor Lévai、Kata Antal、György Tibor Balogh、Tünde Tóth、Péter Huszthy

  DOI：10.1016/j.tetasy.2012.04.008

  日期：2012.4

  This paper reports the preparation and testing of three new pyridino-18-crown-6 ether-based chiral stationary phases (S,S)-CSP-12, (S,S)-CSP-17 and (S,S)-CSP-20. Secondary amine (S,S)-7 was first transformed to triethoxysilyl derivative (S,S)-11, which contains a urea unit by treating the former with 3-(triethoxysilyl)propyl isocyanate. Next, (S,S)-11 was heated with spherical HPLC quality silica gel in toluene to obtain (S,S)-CSP-12. In order to acetylate the 3-aminopropylsilyl groups bonded to the silica gel during immobilization of the triethoxysilyl derivative (S,S)-11, we pumped acetic anhydride and triethylamine in DMF through the column to give the modified chiral stationary phase (S,S)-CSP-20.Triflate (S,S)-13 was first transformed to a pyridino-18-crown-6 ether derivative (S,S)-15, which contains a 4-(methoxycarbonyl)phenyl substituent at the 4-position of the pyridine ring by a Suzuki carbon-carbon coupling reaction. The hydrolysis of ester (S,S)-15 gave carboxylic acid (S,S)-21. Carboxylic acid (S,S)-21 was reacted with an excess of thionyl chloride to form the appropriate acyl chloride, which was treated with 3-(triethoxysilyl)propylamine in the presence of triethylamine in THF to furnish triethoxysilyl derivative (S,S)-16 containing an amide unit. Triethoxysilyl derivative (S,S)-16 was heated with spherical HPLC quality silica gel in toluene to give the chiral stationary phase (S,S)-CSP-17.The enantiomer separating ability of chiral stationary phases (S,S)-CSP-12, (S,S)-CSP-17 and (S,S)-CSP-20 were tested by using mixtures of enantiomers of 1-(1-naphthyl)ethylamine hydrogen perchlorate (1-NEA), 1-(2-naphthyl)ethylamine (2-NEA), 1-(4-bromophenyl)ethylamine (Br-PEA) and 1-(4-nitrophenyl)ethylamine hydrogen chloride (NO2-PEA). Chiral stationary phase (S,S)-CSP-17 showed the best enantiomer separating ability for the mixtures of enantiomers of amine compounds amongst the pyridino-crown ether-based CSPs ever synthesized. The high enantioselectivity is probably due to the strong pi-pi interaction of the extended pi system of the aryl-substituted pyridine unit. (C) 2012 Elsevier Ltd. All rights reserved.