2-[(E)-2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl)ethen-1-yl]-1,3-benzothiazole | 464185-98-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-[(E)-2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl)ethen-1-yl]-1,3-benzothiazole
• 英文别名: (E)-2-(2-(2,3,5,6,8,9,11,12-octahydrobenzo[b][1,4,7,10,13]pentaoxacyclopentadecin-15-yl)vinyl)benzo[d]thiazole；15-[(E)-(benzothiazol-2-yl)ethen-1-yl]-2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecine；2-[2-(6,7,9,10,12,13,15,16-Octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecen-2-yl)-vinyl]-benzothiazole；2-[(E)-2-(2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-1(15),16,18-trien-17-yl)ethenyl]-1,3-benzothiazole
• CAS: 464185-98-6
• 化学式: C₂₃H₂₅NO₅S
• 分子量: 427.521
• InChiKey: ZDYQKUKFIPNNDE-SOFGYWHQSA-N

物化性质

• 熔点：
  139-140 °C(Solv: methanol (67-56-1))
• 沸点：
  618.8±65.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[(E)-2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl)ethen-1-yl]-1,3-benzothiazole 在 碘 、 silver perchlorate 作用下， 以 乙腈 为溶剂， 以42%的产率得到18,21,24,27,30-pentaoxa-11-thia-4-azoniapentacyclo[15.13.0.03,15.04,12.05,10]triaconta-1(17),2,4(12),5,7,9,13,15-octaene;perchlorate
  参考文献：
  名称：

  Electrocyclic reaction of crown-containing 2-styrylbenzothiazoles

  摘要：

  发现了含 15-冠-5-的 2-苯并噻唑在光诱导下电环转化为缩合苯并噻唑喹啉衍生物的过程。这一过程伴随着一个 C-N 键的形成和一个氢原子的消除。

  DOI：

  10.1007/s11172-005-0402-5
• 作为产物：
  描述：

  2-甲基苯并噻唑 、 4-甲酰-15-冠-5 在 盐酸 作用下， 反应 8.5h， 以23%的产率得到2-[(E)-2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl)ethen-1-yl]-1,3-benzothiazole
  参考文献：
  名称：

  Ditopic complex formation of the crown-containing 2-styrylbenzothiazole

  摘要：

  通过光学和 X 射线衍射方法研究了含有 15-冠醚片段的 2-苯并噻唑与碱土金属阳离子、质子、Ag+ 和 Hg2+ 形成的络合物。通过冠醚分子和杂环部分这两个中心的参与，该化合物能够与金属阳离子结合。碱土金属阳离子与分子的大环部分形成络合物。在 Ba2+ 的情况下，形成了强夹心络合物。质子与分子杂环片段的 N 原子配位。Ag+ 和 Hg2+ 阳离子与分子的两个中心结合：冠醚片段和杂环残基。

  DOI：

  10.1039/b205305e

文献信息

• Facile Synthesis of Novel 2-Styrylbenzothiazoles Containing Crown Ether Moieties
  作者：Olga A. Fedorova、Elena N. Andryukhina、Sergey P. Gromov

  DOI：10.1055/s-2003-37348

  日期：——

  Novel 2-styrylbenzothiazoles containing crown ether moieties with different combinations of O, S, and N atoms were prepared by condensation of 2-methylbenzothiazole with formyl derivatives of benzocrown ethers in the presence of alkali metal alkoxides or by Wittig reaction. The role of complex formation in these syntheses is discussed.

  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。
• Self-assembly of a (benzothiazolyl)ethenylbenzocrown ether into a sandwich complex and stereoselective [2+2] photocycloaddition
  作者：S. P. Gromov、A. I. Vedernikov、Yu. V. Fedorov、O. A. Fedorova、E. N. Andryukhina、N. E. Shepel'、Yu. A. Strelenko、D. Johnels、U. Edlund、J. Saltiel、M. V. Alfimov

  DOI：10.1007/s11172-006-0005-9

  日期：2005.7

  In the presence of Ba2+ ions, (benzothiazolyl)ethenylbenzocrown ether forms the stable sandwich complex 2L⋅Ba2+ with an unusual structure, in which the benzothiazole fragments are arranged one above the other. Irradiation of the sandwich complex with visible light induces stereoselective [2+2] cycloaddition giving rise to two “head-to-head” isomers of biscrown-cyclobutane. The addition of dibasic dicarboxylic

  在 Ba2+ 离子的存在下，（苯并噻唑基）乙烯基苯并冠醚形成稳定的夹心复合物 2L⋅Ba2+，具有不寻常的结构，其中苯并噻唑碎片排列在另一个之上。用可见光照射夹心复合物会诱导立体选择性 [2+2] 环加成，产生双冠环丁烷的两种“头对头”异构体。额外稳定夹心复合物在有利构象中的二元二羧酸的添加影响形成的环丁烷的异构体比率。夹心复合物和环丁烷的构象平衡通过 1 H NMR 光谱进行了研究。
• Photoinduced guest transformation promotes translocation of guest from hydroxypropyl-β-cyclodextrin to cucurbit[7]uril
  作者：Yuri V. Fedorov、Sergey V. Tkachenko、Ekaterina Yu. Chernikova、Ivan A. Godovikov、Olga A. Fedorova、Lyle Isaacs

  DOI：10.1039/c4cc08474h

  日期：——

  (1 or 2) and two hosts (hydroxypropyl-beta-cyclodextrin (HP-beta-CD) and cucurbit[7]uril (CB[7])) undergo photoinduced transformation and translocation of the styryl guest from the cavity of HP-beta-CD to CB[7]. We find that the protonation of guest trans-1 or the addition of Ba(2+) as competitor for CB[7] triggers dissociation of the container-guest complexes.

  我们报告说，由苯乙烯基染料（1或2）和两个主体（羟丙基-β-环糊精（HP-β-CD）和葫芦[7]尿素（CB [7]）组成的三组分系统经历了光诱导的转化和转位。从HP-β-CD腔到CB的苯乙烯客体[7]。我们发现来宾反式1的质子化或添加Ba（2+）作为CB [7]的竞争者触发了容器-客体复合物的解离。
• ——
  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.
• ——
  作者：Yu. V. Fedorov、O. A. Fedorova、S. P. Gromov、M. B. Bobrovskii、E. N. Andryukhina、M. V. Alfimov

  DOI：10.1023/a:1016072414801

  日期：——

  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.