6-mercapto-hexyl E-3-(4-diethylamino-2-hydroxy-phenyl)propenoate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 6-mercapto-hexyl E-3-(4-diethylamino-2-hydroxy-phenyl)propenoate
• 英文别名: 6-sulfanylhexyl (E)-3-[4-(diethylamino)-2-hydroxyphenyl]prop-2-enoate
• 化学式: C₁₉H₂₉NO₃S
• 分子量: 351.51
• InChiKey: UNVMOYSFOMQBQE-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  50.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-溴正己醇 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 、 sodium thiomethoxide 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 92.25h， 生成 6-mercapto-hexyl E-3-(4-diethylamino-2-hydroxy-phenyl)propenoate
  参考文献：
  名称：

  Visible Light Excitation of CdSe Nanocrystals Triggers the Release of Coumarin from Cinnamate Surface Ligands

  摘要：

  The photochemical properties of organic ligands on the surface of nanocrystalline CdSe particles were examined. A number of thiols carrying a substituted cinnamate tail was synthesized. In solution, these cinnamate compounds undergo light-induced ( 374 nm) E-Z isomerization, followed by a nonphotolytic lactonization to give highly fluorescent coumarin. The cinnamate-thiols were successfully exchanged onto the CdSe nanocrystal, and the photochemical behavior of these conjugates was studied. Upon aerobic photolysis at 374 nm, the surface cinnamates released coumarin accompanied by rapid nanocrystal degradation. This degradation was not observed under similar anaerobic conditions or when the organic ligands did not contain the cinnamate group. Surprisingly, very similar results were obtained upon irradiation at visible wavelengths at which the cinnamate has no absorption. With the aid of UV-visible absorption spectroscopy, fluorescence spectroscopy, and electrochemistry, a unified theory for both the increased photoinstability of the nanocrystal as well as the coumarin release was proposed. It involves cinnamate radical anions on the CdSe surface, formed upon electron transfer from the excited nanocrystal to the surface cinnamate, undergoing E-Z isomerization. Practically, this results in the remarkable ability to release coumarin from nanocrystal ligands simply by exciting the nanocrystal with visible light. This new photorelease protocol not only aids in the understanding of fundamental nanocrystal-ligand interactions but may also offer new opportunities in the areas of drug delivery and imaging.

  DOI：

  10.1021/ja063562c

文献信息

• Visible Light Excitation of CdSe Nanocrystals Triggers the Release of Coumarin from Cinnamate Surface Ligands
  作者：Maikel Wijtmans、Sandra J. Rosenthal、Binne Zwanenburg、Ned A. Porter

  DOI：10.1021/ja063562c

  日期：2006.9.1

  The photochemical properties of organic ligands on the surface of nanocrystalline CdSe particles were examined. A number of thiols carrying a substituted cinnamate tail was synthesized. In solution, these cinnamate compounds undergo light-induced ( 374 nm) E-Z isomerization, followed by a nonphotolytic lactonization to give highly fluorescent coumarin. The cinnamate-thiols were successfully exchanged onto the CdSe nanocrystal, and the photochemical behavior of these conjugates was studied. Upon aerobic photolysis at 374 nm, the surface cinnamates released coumarin accompanied by rapid nanocrystal degradation. This degradation was not observed under similar anaerobic conditions or when the organic ligands did not contain the cinnamate group. Surprisingly, very similar results were obtained upon irradiation at visible wavelengths at which the cinnamate has no absorption. With the aid of UV-visible absorption spectroscopy, fluorescence spectroscopy, and electrochemistry, a unified theory for both the increased photoinstability of the nanocrystal as well as the coumarin release was proposed. It involves cinnamate radical anions on the CdSe surface, formed upon electron transfer from the excited nanocrystal to the surface cinnamate, undergoing E-Z isomerization. Practically, this results in the remarkable ability to release coumarin from nanocrystal ligands simply by exciting the nanocrystal with visible light. This new photorelease protocol not only aids in the understanding of fundamental nanocrystal-ligand interactions but may also offer new opportunities in the areas of drug delivery and imaging.