(5E)-5-[[6-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxycarbonyloxy]-1-methylquinolin-1-ium-2-yl]methylidene]-2-[(E)-[6-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxycarbonyloxy]-1-methylquinolin-2-ylidene]methyl]-3,4-dioxocyclopenten-1-olate | 1005495-54-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (5E)-5-[[6-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxycarbonyloxy]-1-methylquinolin-1-ium-2-yl]methylidene]-2-[(E)-[6-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxycarbonyloxy]-1-methylquinolin-2-ylidene]methyl]-3,4-dioxocyclopenten-1-olate
• CAS: 1005495-54-4
• 化学式: C₈₃H₁₀₈N₂O₉
• 分子量: 1277.78
• InChiKey: SEYSPMWLCZAVMI-HPRXFZADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.3
• 重原子数：
  94
• 可旋转键数：
  20
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  cholesteryl N-methyl-2-quinaldinium-6-yl carbonate iodide 、 巴豆酸 在 喹啉 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以75%的产率得到(5E)-5-[[6-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxycarbonyloxy]-1-methylquinolin-1-ium-2-yl]methylidene]-2-[(E)-[6-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxycarbonyloxy]-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

文献信息

• Infrared Absorbing Croconaine Dyes:  Synthesis and Metal Ion Binding Properties
  作者：Rekha R. Avirah、Kuthanapillil Jyothish、Danaboyina Ramaiah

  DOI：10.1021/jo702209a

  日期：2008.1.1

  [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.