6-iodo-N-methyl-2-quinaldinium iodide | 10352-61-1

• 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: 6-iodo-N-methyl-2-quinaldinium iodide
• 英文别名: 6-iodo-N-methyl-quinaldinium iodide；6-iodo-1-methylquinaldinium iodide；Quinolinium, 6-iodo-1,2-dimethyl-, iodide；6-iodo-1,2-dimethylquinolin-1-ium;iodide
• CAS: 10352-61-1
• 化学式: C₁₁H₁₁IN*I
• 分子量: 411.024
• InChiKey: BQJPYSSQNMWRTF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.42
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  3.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  巴豆酸 、 6-iodo-N-methyl-2-quinaldinium iodide 在 喹啉 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以85%的产率得到5-[(6-Iodo-1-methylquinolin-1-ium-2-yl)methylidene]-2-[(6-iodo-1-methylquinolin-2-ylidene)methyl]-3,4-dioxocyclopenten-1-olate
  参考文献：
  名称：

  Infrared Absorbing Croconaine Dyes:  Synthesis and Metal Ion Binding Properties

  摘要：

  [GRAPHICS]Quinaldine-based croconaine dyes synthesized by the condensation reaction between croconic acid and the respective quinaldinium salts are described. These dyes exhibit absorption maximum in the infrared region (840-870 nm) with high molar extinction coefficients (1-5 x 10(5) M-1 cm(-1)) and have very low fluorescence quantum yields. Upon binding to divalent metal ions, these dyes were found to form complexes with a 2:1 stoichiometry having high association constants of the order of 10(11)-10(14) M-2, while the monovalent metal ions showed negligible affinity. The binding of the croconaine dye 3d with divalent metal ions especially Zn2+, Pb2+, and Cd2+ led to significant chelation-enhanced fluorescence emission. The broadening of the aromatic signals, vinylic and N-methyl protons and the negligible changes at the aliphatic region of the dye 3d in the H-1 NMR spectrum in the presence of Zn2+, indicate that the binding occurs at the carbonyl groups of the croconyl ring. The shift in the croconyl carbonyl stretching frequency in the [3d-Zn2+] complex analyzed through FT-IR analysis further confirms the involvement of two electron-rich carbonyl groups of the croconyl moiety in the complexation. These results demonstrate that the binding of the divalent metal ions at the carbonyl oxygens of these infrared absorbing dyes can be favorably utilized for the development of potential sensors for the detection of metal ions and further can be exploited as sensitizers for photodynamic therapeutic applications.

  DOI：

  10.1021/jo702209a
• 作为产物：
  描述：

  对碘苯胺 在 盐酸 作用下， 以 甲苯 、 正丁醇 为溶剂， 反应 12.0h， 生成 6-iodo-N-methyl-2-quinaldinium iodide
  参考文献：
  名称：

  Shevchuk, M. I.; Chernyuk, I. N.; Volynskaya, E. M., Journal of general chemistry of the USSR, 1980, vol. 50, # 9, p. 1595 - 1597

  摘要：

  DOI：

文献信息

• Novel semisquaraine regioisomers: isolation, divergent chemical reactivity and photophysical properties
  作者：Rekha R. Avirah、Kuthanapillil Jyothish、Cherumuttathu H. Suresh、Eringathodi Suresh、Danaboyina Ramaiah

  DOI：10.1039/c1cc15261k

  日期：——

  A zwitterionic semisquaraine 1,3-regioisomer which exhibits distinct photophysical properties and chemical reactivity was isolated. Uniquely, this isomer has been identified as the reactive intermediate in the squaraine dye formation reaction rather than the neutral 1,2-isomer and opens up new avenues for the synthesis of novel dyes for optoelectronic applications.

  一种具有独特光物理特性和化学反应性的两性离子半方形酮1,3-区异构体被分离出来。独特的是，这种异构体被确定为方形染料形成反应中的反应中间体，而非中性1,2-异构体，为新型染料的合成开辟了新的途径，以用于光电应用。
• Shevchuk, M. I.; Chernyuk, I. N.; Volynskaya, E. M., Journal of general chemistry of the USSR, 1980, vol. 50, # 9, p. 1595 - 1597
  作者：Shevchuk, M. I.、Chernyuk, I. N.、Volynskaya, E. M.、Shelest, V. V.、Yagodinets, P. I.

  DOI：——

  日期：——
• Synthesis of New Cholesterol- and Sugar-Anchored Squaraine Dyes:  Further Evidence of How Electronic Factors Influence Dye Formation
  作者：Kuthanapillil Jyothish、Rekha R. Avirah、Danaboyina Ramaiah

  DOI：10.1021/ol052639j

  日期：2006.1.1

  Synthesis of new quinaldine-based squaraine dyes linked to cellular recognition elements that exhibit near-infrared absorption (> 740 nm) are described. Both product analysis and theoretical calculations substantiate the interesting electronic effects of various substituents in the dye formation reaction. These results are useful in the synthesis of symmetrical and unsymmetrical squaraine dyes that can have potential biological and photodynamic therapeutical applications.
• SHEVCHUK M. I.; CHERNYUK I. N.; VOLYNSKAYA E. M.; SHELEST V. V.; YAGODINE+, ZH. OBSHCH. XIMII, 1980, 50, HO 9, 1978-1981
  作者：SHEVCHUK M. I.、 CHERNYUK I. N.、 VOLYNSKAYA E. M.、 SHELEST V. V.、 YAGODINE+

  DOI：——

  日期：——
• CHERNYUK I. N.; SHELEST V. V.; ALBOTA L. A.; PILYUGIN G. T.; BIBIK L. I., ZH. ORGAN. XIMII <ZORK-AE>, 1976, 12, HO 2, 452-455
  作者：CHERNYUK I. N.、 SHELEST V. V.、 ALBOTA L. A.、 PILYUGIN G. T.、 BIBIK L. I.

  DOI：——

  日期：——