N-[(1E,3E)-4-(1-ethyl-3,3-dimethylindol-1-ium-2-yl)buta-1,3-dienyl]-N-phenylacetamide | 788815-60-1

• 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: N-[(1E,3E)-4-(1-ethyl-3,3-dimethylindol-1-ium-2-yl)buta-1,3-dienyl]-N-phenylacetamide
• CAS: 788815-60-1
• 化学式: C₂₄H₂₇N₂O
• 分子量: 359.491
• InChiKey: YPPIMUGWNBCQRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  23.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-[(1E,3E)-4-(1-ethyl-3,3-dimethylindol-1-ium-2-yl)buta-1,3-dienyl]-N-phenylacetamide 、 1-ethyl-2,3,3-trimethyl-3H-indolium bromide 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 1-ethyl-2-((1E,3E)-5-((E)-1-ethyl-3,3-dimethylindolin-2-ylidene)penta-1,3-dien-1-yl)-3,3-dimethyl-3H-indol-1-ium
  参考文献：
  名称：

  Symmetrical and Asymmetrical Cyanine Dyes. Synthesis, Spectral Properties, and BSA Association Study

  摘要：

  New cyanines were prepared by an efficient and practical route with satisfactory overall yield from low-cost starting materials. The photophysical behavior of the cyanines was investigated using UV-vis and steady-state fluorescence in solution, as well as their association with bovine serum albumin (BSA) in phosphate buffer solution (PBS). No cyanine aggregation was observed in organic solvents or in phosphate buffer solution. The alkyl chain length in the quaternized nitrogen was shown to be fundamental for BSA detection in PBS in these dyes.

  DOI：

  10.1021/jo500657s
• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚 以 邻二氯苯 为溶剂， 反应 26.0h， 生成 N-[(1E,3E)-4-(1-ethyl-3,3-dimethylindol-1-ium-2-yl)buta-1,3-dienyl]-N-phenylacetamide
  参考文献：
  名称：

  Symmetrical and Asymmetrical Cyanine Dyes. Synthesis, Spectral Properties, and BSA Association Study

  摘要：

  New cyanines were prepared by an efficient and practical route with satisfactory overall yield from low-cost starting materials. The photophysical behavior of the cyanines was investigated using UV-vis and steady-state fluorescence in solution, as well as their association with bovine serum albumin (BSA) in phosphate buffer solution (PBS). No cyanine aggregation was observed in organic solvents or in phosphate buffer solution. The alkyl chain length in the quaternized nitrogen was shown to be fundamental for BSA detection in PBS in these dyes.

  DOI：

  10.1021/jo500657s

文献信息

• Novel asymmetric indodicarbocyanine dyes
  作者：V. E. Kuznetsova、A. V. Davydov、V. A. Vasiliskov、A. A. Stomakhin、A. V. Chudinov、A. S. Zasedatelev

  DOI：10.1007/s11172-007-0356-x

  日期：2007.11

  Novel indodicarbocyanine dyes functionalized at position 5 of the indolenine system were obtained and characterized by spectroscopic methods.

  获得了在吲哚啉系统的第 5 位官能化的新型吲哚二羰花青染料，并通过光谱方法对其进行了表征。
• New indodicarbocyanine dyes for the biological microchip technology
  作者：V. E. Kuznetsova、V. A. Vasiliskov、O. V. Antonova、V. M. Mikhailovich、A. S. Zasedatelev、A. V. Chudinov

  DOI：10.1134/s1068162008010184

  日期：2008.1

  New indodicarbocyanine dyes with the carboxybutyl group in position-3 of the indolenine fragment bearing methyl and sulfonic groups in positions 5 and 7 of the cycle were synthesized in order to find the most effective fluorescent labels for the biological microchip technology. The position of absorption and fluorescence maxima, the total charge of the dye molecule, and water solubility depend on the location and the total amount of methyl and sulfonic groups. The spectral characteristics of the dyes synthesized were determined. The relative fluorescence efficiencies of the dyes at equal concentrations were measured at excitation wavelengths of 635 and 655 nm and emission wavelengths of 670 and 690 nm, respectively.

  为寻找生物微芯片技术中最有效的荧光标记物，合成了吲哚碳菁染料，其吲哚啉部分的3位带有羧丁基，环的5位和7位分别带有甲基和磺酸基。染料的吸收和荧光最大值位置、分子总电荷以及水溶性取决于甲基和磺酸基的位置和总量。测定了所合成染料的光谱特性，并在激发波长为635nm和655nm，发射波长为670nm和690nm时，分别测量了等浓度染料的相对荧光效率。
• Water-soluble cyanine dyes for biological microchip technology
  作者：V. E. Kuznetsova、T. A. Luk’yanova、V. A. Vasiliskov、O. V. Kharitonova、A. V. Chudinov、A. S. Zasedatelev

  DOI：10.1007/s11172-007-0387-3

  日期：2007.12

  Novel indodicarbocyanine dyes were obtained and their spectroscopic characteristics were determined. For equal concentrations of the dyes, the relative fluorescence efficiency was measured at the excitation wavelengths λ = 635 and 655 nm and the emission wavelengths λ = 670 and 690 nm, respectively.

  新型吲哚二碳菁染料被合成，并测定了它们的谱学特性。对于等浓度的染料，在激发波长 λ = 635 nm 和 655 nm，以及发射波长 λ = 670 nm 和 690 nm 处，分别测量了相对荧光效率。
• Synthesis, properties and bioconjugation of water-soluble asymmetric indodicarbocyanine dyes
  作者：Viktoriya E. Kuznetsova、Vadim A. Vasiliskov、Aleksandr S. Zasedatelev、Aleksandr V. Chudinov

  DOI：10.1016/j.mencom.2008.05.009

  日期：2008.5

  New indodicarbocyanine dyes have been synthesised and converted into succinimidyl active esters for the fluorescent labeling of proteins and oligonucleotides.
• Symmetrical and Asymmetrical Cyanine Dyes. Synthesis, Spectral Properties, and BSA Association Study
  作者：Diego S. Pisoni、Letícia Todeschini、Antonio César A. Borges、Cesar L. Petzhold、Fabiano S. Rodembusch、Leandra F. Campo

  DOI：10.1021/jo500657s

  日期：2014.6.20

  New cyanines were prepared by an efficient and practical route with satisfactory overall yield from low-cost starting materials. The photophysical behavior of the cyanines was investigated using UV-vis and steady-state fluorescence in solution, as well as their association with bovine serum albumin (BSA) in phosphate buffer solution (PBS). No cyanine aggregation was observed in organic solvents or in phosphate buffer solution. The alkyl chain length in the quaternized nitrogen was shown to be fundamental for BSA detection in PBS in these dyes.