3-{4-[(E)-2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl)-1-ethenyl]-1-quinoliniumyl}-1-propanesulfonate | 583854-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-{4-[(E)-2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl)-1-ethenyl]-1-quinoliniumyl}-1-propanesulfonate
• 英文别名: 4-[2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-pentaoxabenzocyclopentadecin-16-yl)ethenyl]-1-(3-sulfopropyl)quinolinium betaine；3-[4-[(E)-2-(2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-1(15),16,18-trien-17-yl)ethenyl]quinolin-1-ium-1-yl]propane-1-sulfonate
• CAS: 583854-86-8
• 化学式: C₂₈H₃₃NO₈S
• 分子量: 543.638
• InChiKey: MTYOTOYQGWOYIU-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-{4-[(E)-2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl)-1-ethenyl]-1-quinoliniumyl}-1-propanesulfonate 在 magnesium(II) perchlorate 作用下， 以 乙腈 为溶剂， 生成 3-(4-{2,4-di(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl)-3-[1-(3-sulfonatopropyl)-4-quinoliniumyl]cyclobutyl}-1-quinoliniumyl)-1-propanesulfonate
  参考文献：
  名称：

  Crown-ether styryl dyes

  摘要：

  Styryl dyes (4a,b) containing a 15-crown-5 fragment and isomeric 2- and 4-quinolinium residues with an N-sulfopropyl substituent undergo [2+2] -autophotocycloaddition to give cyclobutane derivatives (9a,b) in acetonitrile only in the presence of Mg(ClO4)(2) or Ca(ClO4)(2). The stereospecificity of both pathways of photocycloaddition and its efficiency are explained by the preorganization of the supramolecular dimers derived from the trans-isomers of the dyes when they are bound into complexes with Mg and Ca cations.

  DOI：

  10.1007/bf00696719
• 作为产物：
  描述：

  4-甲基喹啉 在 吡啶 作用下， 以 乙醇 、 苯 为溶剂， 反应 20.0h， 生成 3-{4-[(E)-2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl)-1-ethenyl]-1-quinoliniumyl}-1-propanesulfonate
  参考文献：
  名称：

  Crown-ether styryl dyes

  摘要：

  Styryl dyes (4a,b) containing a 15-crown-5 fragment and isomeric 2- and 4-quinolinium residues with an N-sulfopropyl substituent undergo [2+2] -autophotocycloaddition to give cyclobutane derivatives (9a,b) in acetonitrile only in the presence of Mg(ClO4)(2) or Ca(ClO4)(2). The stereospecificity of both pathways of photocycloaddition and its efficiency are explained by the preorganization of the supramolecular dimers derived from the trans-isomers of the dyes when they are bound into complexes with Mg and Ca cations.

  DOI：

  10.1007/bf00696719

文献信息

• Novel Photoswitchable Receptors:  Synthesis and Cation-Induced Self-Assembly into Dimeric Complexes Leading to Stereospecific [2+2]-Photocycloaddition of Styryl Dyes Containing a 15-Crown-5 Ether Unit
  作者：Sergey P. Gromov、Evgeny N. Ushakov、Olga A. Fedorova、Igor I. Baskin、Alexei V. Buevich、Elena N. Andryukhina、Michael V. Alfimov、Dan Johnels、Ulf G. Edlund、James K. Whitesell、Marye Anne Fox

  DOI：10.1021/jo034460x

  日期：2003.8.1

  Styryl dyes 4a-e containing a 15-crown-5 ether unit and a quinoline residue with a sulfonatoalkyl or sulfonatobenzyl N-substituent were synthesized. The relationship between the photochemical behavior of these dyes and their aggregates derived from complexation with Mg2+ in MeCN was studied using H-1 NMR and absorption spectroscopy. The E-isomers of 4a-e were shown to form highly stable dimeric (2:2) complexes with Mg2+. Upon irradiation with visible light, the dimeric complexes undergo two competing photoreactions, viz., geometric E --> Z isomerization, resulting in an anion-capped 1:1 complex of the Z-isomer with Mg2+ and stereospecific syn-head-to-tail [2+2]-cycloaddition, affording a single isomer of bis-crown-containing cyclobutane. The N-substituent in the dye has a dramatic effect on the photochemical behavior of the dimeric complex. Molecular dynamics and semiempirical quantum-chemical calculations were carried out to interpret the observed photocycloaddition in the dimer. Conformational equilibria for the dimer of (E)-4b were analyzed using H-1 NMR spectroscopy.