15-[(E)-(benzothiazol-2-yl)ethen-1-yl]-7-methyl-2,3,5,6,8,9,1 l,12-octahydro-5H-1,4,10,13,7-benzotetraoxaazacyclopentadecine | 464186-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 15-[(E)-(benzothiazol-2-yl)ethen-1-yl]-7-methyl-2,3,5,6,8,9,1 l,12-octahydro-5H-1,4,10,13,7-benzotetraoxaazacyclopentadecine
• 英文别名: 17-[(E)-2-(1,3-benzothiazol-2-yl)ethenyl]-8-methyl-2,5,11,14-tetraoxa-8-azabicyclo[13.4.0]nonadeca-1(15),16,18-triene
• CAS: 464186-00-3
• 化学式: C₂₄H₂₈N₂O₄S
• 分子量: 440.563
• InChiKey: JENPMJFPZYJOFN-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  15-[(E)-(benzothiazol-2-yl)ethen-1-yl]-7-methyl-2,3,5,6,8,9,1 l,12-octahydro-5H-1,4,10,13,7-benzotetraoxaazacyclopentadecine 以 乙腈 为溶剂， 生成 2-((Z)-2-Benzothiazol-2-yl-vinyl)-11-methyl-6,7,10,11,12,13,15,16-octahydro-9H-5,8,14,17-tetraoxa-11-aza-benzocyclopentadecene
  参考文献：
  名称：

  摘要：

  The photochromic properties and complex formation of 2-styrylbenzothiazoles containing different crown ether moieties with alkaline-earth metals were described using optical methods, NMR spectroscopy, and HPLC. The large ionochromic effect and fluorescence quenching on complex formation with alkali-earth metal cations were found for 2-styrylbenzothiazole containing the phenylazacrown ether moiety. The small ionochromic effect and fluorescence enhancement of complex formation with alkali-earth metal cations were found for 2-styrylbenzothiazole containing the benzocrown ether moiety. cis-isomers of 2-styrylbenzothiazoles were stable in the dark in acetonitrile. The method for separation of cis-isomers of 2-styrylbenzothiazoles by HPLC was proposed.

  DOI：

  10.1023/a:1016072414801
• 作为产物：
  描述：

  2-甲基苯并噻唑 、 7-methyl-2,3,6,7,8,9,11,12-octahydro-5H-1,4,10,13,7-benzotetraoxaazacyclopentadecine-15-carbaldehyde 在 sodium ethanolate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以45%的产率得到15-[(E)-(benzothiazol-2-yl)ethen-1-yl]-7-methyl-2,3,5,6,8,9,1 l,12-octahydro-5H-1,4,10,13,7-benzotetraoxaazacyclopentadecine
  参考文献：
  名称：

  含有冠醚部分的新型 2-苯乙烯基苯并噻唑的简便合成

  摘要：

  通过 2-甲基苯并噻唑与苯并冠醚的甲酰基衍生物在碱金属醇盐的存在下缩合或通过 Wittig 反应制备新型 2-苯乙烯基苯并噻唑，其含有具有不同 O、S 和 N 原子组合的冠醚部分。讨论了复合物形成在这些合成中的作用。

  DOI：

  10.1055/s-2003-37348

文献信息

• ——
  作者：O. A. Fedorova、E. N. Andryukhina、A. V. Lindeman、S. S. Basok、T. Yu. Bogaschenko、S. P. Gromov

  DOI：10.1023/a:1015416029124

  日期：——

  Methods for the synthesis of unknown 2-styrylbenzothiazoles containing crown ether moieties with different combinations of O, S, and N-heteroatoms based on the Wittig reaction or condensation of 2-methylbenzothiazole with crown-ether benzaldehydes in the presence of strong bases or acids are proposed. The condensation in the presence of bases is accompanied by complex formation with participation of the crown ether moiety of the benzaldehyde. The complex formation has a pronounced influence on the yield of the target product and the pattern of condensation of 2-methylbenzothiazole with crown-ether benzaldehydes.