3-ethyl-2-[(1E,3E,5E)-6-methyl(phenyl)carboxamidohexa-1,3,5-trienyl]-1,3-benzothiazolium iodide | 35874-25-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-ethyl-2-[(1E,3E,5E)-6-methyl(phenyl)carboxamidohexa-1,3,5-trienyl]-1,3-benzothiazolium iodide
• 英文别名: 2-{(1E,3E,5E)-6-[acetyl(phenyl)amino]hexa-1,3,5-trien-1-yl}-3-ethyl-1,3-benzothiazolium iodide；2-[6-(N-acetyl-anilino)-hexa-1,3,5-trienyl]-3-ethyl-benzothiazolium; iodide；2-[6-(N-Acetyl-anilino)-hexa-1,3,5-trienyl]-3-aethyl-benzothiazolium; Jodid；N-[6-(3-ethyl-1,3-benzothiazol-3-ium-2-yl)hexa-1,3,5-trienyl]-N-phenylacetamide;iodide
• CAS: 35874-25-0
• 化学式: C₂₃H₂₃N₂OS*I
• 分子量: 502.419
• InChiKey: LBMNISZFKDUUOA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  52.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-ethyl-2-[(1E,3E,5E)-6-methyl(phenyl)carboxamidohexa-1,3,5-trienyl]-1,3-benzothiazolium iodide 在 甲醇 、 potassium iodide 作用下， 生成 3-ethyl-2-(6-piperidino-hexa-1,3,5-trienyl)-benzothiazolium; iodide
  参考文献：
  名称：

  Ogata; Sugimoto, Kagaku Kenkyusho Hokoku, 1951, vol. 27, p. 332,335

  摘要：

  DOI：
• 作为产物：
  描述：

  3-乙基-2-甲基苯并噻唑碘化物 、 乙酸酐 、 glutaconaldehyde dianilide monohydrochloride 生成 3-ethyl-2-[(1E,3E,5E)-6-methyl(phenyl)carboxamidohexa-1,3,5-trienyl]-1,3-benzothiazolium iodide
  参考文献：
  名称：

  Synthesis and spectral properties of malononitrile-based merocyanine dyes

  摘要：

  合成了由美克腈和具有中等（染料1-6）、强（染料7-9）及弱（染料10和11）电子供给能力的杂环衍生的二甲、四甲和六甲美克腈。美克腈10和11的电子结构类似于中性聚烯状态，而7-9的电子结构则更接近理想的聚美烯状态。随着聚美烯链长的增加，这些趋势变得更加明显。由具有弱或中等电子供给能力的杂环残基衍生的美克腈表现出正溶剂色变，而那些具有强电子供给能力的则表现出负溶剂色变。溶剂极性的增加使得前者的化合物更类似于聚美烯，而后者则更类似于在末端基团带有相反电荷的聚烯。对导致观察到的特征特性的因素（非特异性溶剂化、特异性亲核和亲电子溶剂化以及振动耦合效应）进行了分析。

  DOI：

  10.1007/s11172-006-0196-0

文献信息

• Studies in the Cyanine Dye Series. XI.¹ The Merocyanines
  作者：L. G. S. Brooker、G. H. Keyes、R. H. Sprague、R. H. VanDyke、E. VanLare、G. VanZandt、F. L. White

  DOI：10.1021/ja01155a095

  日期：1951.11
• Sensitized photographic emulsions
  申请人：EASTMAN KODAK CO

  公开号：US02721799A1

  公开（公告）日：1955-10-25
• DE922729
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis, structure, and solvatochromism of merocyanine dyes based on barbituric acid
  作者：A. V. Kulinich、N. A. Derevyanko、A. A. Ishchenko

  DOI：10.1134/s1070363206090167

  日期：2006.9

  Di-, tetra-, and hexamethinemerocyanines were synthesized on the basis of barbituric and 1,3-dimethylbarbituric acids and heterocycles characterized by a strong (1-benzyl-1,2-dihydrobenzo[cd]indole), medium (1,3-dihydro-1,3,3-trimethyl-2H-indole and 3-ethyl-2,3-dihydro-1,3-benzothiazole), and strong electron-donor power (1,3-diphenyl-2,3-dihydro-1H-benzirnidazole). Their solvatochromic properties were analyzed using both conventional parameters (absorption maxima and molar absorption coefficients) and centroids, oscillator strengths, widths, asymmetry and excess coefficients, and fine structure of the long-wave absorption bands, which were determined by mathematical processing (method of moments). A combination of these parameters unambiguously characterizes limiting electronic states of merocyanines (neutral polyene, polymethine, or charged polyene) responsible for the type of solvatochronism. Relations were found between solvatochromic properties, on the one hand, and donor-acceptor power of the terminal groups, length of the polymethine chain, and solvent nature, on the other. The difference in solvatochromism (up to reversal of sign) of merocyanines derived from barbituric acid and their analogs based on 1,3-dimethylbarbituric acid originates from both the difference in their electronic asymmetry and the ability of the NH groups in the former to participate in hydrogen bonding with proton-acceptor solvents.
• Ogata, Rikagaku Kenkyusho Iho, 1937, vol. 16, p. 583,587
  作者：Ogata

  DOI：——

  日期：——