2,6-dimethyl-4-(4-dimethylaminostyryl)pyrylium perchlorate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2,6-dimethyl-4-(4-dimethylaminostyryl)pyrylium perchlorate
• 英文别名: [4-[2-(2,6-Dimethylpyran-4-ylidene)ethylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium;perchlorate
• 化学式: C₁₇H₂₀NO*ClO₄
• 分子量: 353.803
• InChiKey: UAUVIFNYGPXUGX-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.24
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  86.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4-二氨基甲苯 、 2,6-dimethyl-4-(4-dimethylaminostyryl)pyrylium perchlorate 以 乙醇 为溶剂， 以45%的产率得到1-(3-amino-4-methylphenyl)-4-[4-(dimethylamino)styryl]-2,6-dimethylpyridinium perchlorate
  参考文献：
  名称：

  Detection of anilines by luminescence spectroscopy using dissolved and adsorbed pyrylocyanine dyes

  摘要：

  为了开发检测芳香胺的方法，研究了三种吡咯菁染料（由 2,4,6-三甲基吡咯菁高氯酸盐衍生而来）与对甲苯胺和 2,4-二氨基甲苯的反应。研究人员考察了起始染料以及在溶液中和硅胶上获得的最终产物的发射光谱特征。通过分析反应中间产物的激发光谱和发射光谱，发现在乙腈中存在开放形式的吡啶菁染料。在溶液中形成发光的吡啶菁需要数天时间，而从吸附在硅胶上的起始染料合成吡啶菁则在几秒钟内完成。

  DOI：

  10.1007/s11172-014-0485-y
• 作为产物：
  描述：

  2,4,6-三甲基吡喃鎓高氯酸盐 、 对二甲氨基苯甲醛 以 甲醇 为溶剂， 反应 4.0h， 生成 2,6-dimethyl-4-(4-dimethylaminostyryl)pyrylium perchlorate
  参考文献：
  名称：

  Detection of anilines by luminescence spectroscopy using dissolved and adsorbed pyrylocyanine dyes

  摘要：

  为了开发检测芳香胺的方法，研究了三种吡咯菁染料（由 2,4,6-三甲基吡咯菁高氯酸盐衍生而来）与对甲苯胺和 2,4-二氨基甲苯的反应。研究人员考察了起始染料以及在溶液中和硅胶上获得的最终产物的发射光谱特征。通过分析反应中间产物的激发光谱和发射光谱，发现在乙腈中存在开放形式的吡啶菁染料。在溶液中形成发光的吡啶菁需要数天时间，而从吸附在硅胶上的起始染料合成吡啶菁则在几秒钟内完成。

  DOI：

  10.1007/s11172-014-0485-y

文献信息

• Synthesis and Characterization of Mono-, Bis-, and Trissubstituted Pyridinium and Pyrylium Dyes
  作者：Masaki Matsui、Shigeo Kawamura、Katsuyoshi Shibata、Hiroshige Muramatsu

  DOI：10.1246/bcsj.65.71

  日期：1992.1

  A series of mono-, bis-, and trissubstituted pyridinium and pyrylium dyes have been synthesized by the condensation of methylpyridinium and methylpyrylium salts with aldehydes or nitroso compound. Large bathochromic shifts were observed in the following order, both in substituted azomethine pyridinium and pyrylium dyes, mono < bis < tris. The magnitude of the shift appeared in the order of multiple

  通过甲基吡啶鎓和甲基吡啶鎓盐与醛或亚硝基化合物缩合合成了一系列单、双和三取代的吡啶鎓和吡咯鎓染料。在取代的偶氮甲碱吡啶鎓和吡咯鎓染料中，按以下顺序观察到大的红移，单<双<三。位移的大小以多重键的顺序出现，–CH=CH– < –CH=CH–CH=CH– < –CH=N–。
• Carbonic anhydrase inhibitors. Part 24. A quantitative structure-activity relationship study of positively charged sulfonamide inhibitors
  作者：CT Supuran、BW Clare

  DOI：10.1016/0223-5234(96)88286-9

  日期：1995.1

  A quantitative structure-activity relationship (QSAR) study is presented for 28 carbonic anhydrase inhibitors (CAIs), derivatives of tri-, tetra- and penta-substituted 1-(2-sulfonamido-1,3,4-thiadiazol-5-yl)pyridinium perchlorates. Several of these derivatives are new compounds and their synthesis and properties are also reported. The conclusion of the study is that activity is greatly modulated by electronic effects on the pyridinium ring. The most significant effects were enhancement of activity with increased positive charge on this ring, weakening of activity with increasing HOMO energy, and a dependence on anisotropic polarizability which may be attributable to London forces.
• Detection of anilines by luminescence spectroscopy using dissolved and adsorbed pyrylocyanine dyes
  作者：V. V. Shelkovnikov、I. Yu. Kargapolova、S. V. Korotaev、N. A. Orlova、I. P. Chuikov、V. A. Nadolinnyi

  DOI：10.1007/s11172-014-0485-y

  日期：2014.3

  Reactions of three pyrylocyanine dyes (derived from 2,4,6-trimethylpyrylium perchlorate) with p-toluidine and 2,4-diaminotoluene were studied to develop methods for detection of aromatic amines. The emission spectrum characteristics of the starting dyes and the final products obtained in solution and on silica gel were examined. The presence of open forms of the pyridocyanine dye in acetonitrile was suggested after analyzing the excitation and emission spectra of reaction intermediates. The formation of luminescent pyridocyanine in solution took several days, while its synthesis from the starting dye adsorbed on silica gel was completed within a few seconds.

  为了开发检测芳香胺的方法，研究了三种吡咯菁染料（由 2,4,6-三甲基吡咯菁高氯酸盐衍生而来）与对甲苯胺和 2,4-二氨基甲苯的反应。研究人员考察了起始染料以及在溶液中和硅胶上获得的最终产物的发射光谱特征。通过分析反应中间产物的激发光谱和发射光谱，发现在乙腈中存在开放形式的吡啶菁染料。在溶液中形成发光的吡啶菁需要数天时间，而从吸附在硅胶上的起始染料合成吡啶菁则在几秒钟内完成。