13-(2-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}ethylcarbamoyl)tridec-12-enoyl chloride

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 13-(2-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}ethylcarbamoyl)tridec-12-enoyl chloride
• 英文别名: (E)-14-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethylamino]-14-oxotetradec-12-enoyl chloride
• 化学式: C₂₃H₄₂ClNO₆
• 分子量: 464.043
• InChiKey: NEUGUPPKAVUKLX-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  31
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  12-羟基十二酸 在 4-二甲氨基吡啶 、 lithium hydroxide 、 草酰氯 、 sodium hydride 、 potassium hydrogencarbonate 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 73.5h， 生成 13-(2-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}ethylcarbamoyl)tridec-12-enoyl chloride
  参考文献：
  名称：

  Nanowells on Silica Particles in Water Containing Long-Distance Porphyrin Heterodimers

  摘要：

  Smooth and nonswelling spherical silica particles with a diameter of 100 nm and an aminopropyl coating are soluble in water at pH 11, coagulate quickly at pH 3, and redissolve at pH 9. Electron microscopy as well as visible spectra of covalently attached porphyrins indicate the aggregation state of the particles. Long-chain alpha,omega-dicarboxylic acids with a terminal oligoethyleneglycol (=OEG)-amide group were attached in a second self-assembly step to the remaining amine groups around the porphyrins. Form-stable 2-nm wells were thus obtained and were characterized by fluorescence quenching experiments using the bottom porphyrin as a target. The one-dimensional diffusion of fitting quencher molecules along the 2-nm pathway took several minutes. Porphyrins with a diameter above 2 nm could not enter the form-stable gaps at all. Added tyrosine stuck irreversibly to the walls of the nanowells and prevented the entrance of quencher molecules, the OEG-headgroups fixated 2,6-diaminoanthraquinone. A ring of methylammonium groups was then fixed at the walls of the wells at a distance of 5 or 10 Angstrom with respect to the bottom porphyrin. 2,6-Disulfonatoanthraquinone was attached only loosely to this ring, but the exactly fitting manganese(III) meso-(tetraphenyl -4-sulfonato)porphyrinate (Mn(III) TPPS) was tightly bound. Transient fluorescence experiments showed a fast decay time of 0.2 ns for the bottom porphyrin, when the Mn(III) TPPS was fixated at a distance of 5 Angstrom. Two different dyes have thus been immobilized at a defined subnanometer distance in an aqueous medium.

  DOI：

  10.1021/ja035558w

文献信息

• Nanowells on Silica Particles in Water Containing Long-Distance Porphyrin Heterodimers
  作者：Guangtao Li、Sheshanath V. Bhosale、Tianyu Wang、Steffen Hackbarth、Beate Roeder、Ulrich Siggel、Jürgen-Hinrich Fuhrhop

  DOI：10.1021/ja035558w

  日期：2003.9.1

  Smooth and nonswelling spherical silica particles with a diameter of 100 nm and an aminopropyl coating are soluble in water at pH 11, coagulate quickly at pH 3, and redissolve at pH 9. Electron microscopy as well as visible spectra of covalently attached porphyrins indicate the aggregation state of the particles. Long-chain alpha,omega-dicarboxylic acids with a terminal oligoethyleneglycol (=OEG)-amide group were attached in a second self-assembly step to the remaining amine groups around the porphyrins. Form-stable 2-nm wells were thus obtained and were characterized by fluorescence quenching experiments using the bottom porphyrin as a target. The one-dimensional diffusion of fitting quencher molecules along the 2-nm pathway took several minutes. Porphyrins with a diameter above 2 nm could not enter the form-stable gaps at all. Added tyrosine stuck irreversibly to the walls of the nanowells and prevented the entrance of quencher molecules, the OEG-headgroups fixated 2,6-diaminoanthraquinone. A ring of methylammonium groups was then fixed at the walls of the wells at a distance of 5 or 10 Angstrom with respect to the bottom porphyrin. 2,6-Disulfonatoanthraquinone was attached only loosely to this ring, but the exactly fitting manganese(III) meso-(tetraphenyl -4-sulfonato)porphyrinate (Mn(III) TPPS) was tightly bound. Transient fluorescence experiments showed a fast decay time of 0.2 ns for the bottom porphyrin, when the Mn(III) TPPS was fixated at a distance of 5 Angstrom. Two different dyes have thus been immobilized at a defined subnanometer distance in an aqueous medium.