3-{2-[2-(4-hydroxy-3-nitrophenylcarbamoyl)ethoxy]ethoxy}propionic acid | 638177-58-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-{2-[2-(4-hydroxy-3-nitrophenylcarbamoyl)ethoxy]ethoxy}propionic acid
• CAS: 638177-58-9
• 化学式: C₁₄H₁₈N₂O₈
• 分子量: 342.306
• InChiKey: GXUMTOBIYFTOFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.14
• 重原子数：
  24.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  148.23
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-{2-[2-(4-hydroxy-3-nitrophenylcarbamoyl)ethoxy]ethoxy}propionic acid 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 1-羟基苯并三唑一水物 、 三氟乙酸 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-(1,2-Bis-hexadecylcarbamoyl-ethyl)-2-(3-{2-[2-(4-hydroxy-3-nitro-phenylcarbamoyl)-ethoxy]-ethoxy}-propionylamino)-succinamic acid
  参考文献：
  名称：

  Synthesis and Spectroscopic Analysis of Chromophoric Lipids Inducing pH-Dependent Liposome Fusion

  摘要：

  We design novel chromophoric amphiphiles 6a-c, which lead to pH-dependent membrane fusion of egg phosphatidylcholine (eggPC) liposome containing them. Lipids 6a-c comprise double alkyl chains, a single chain with a 2-nitrophenol group as a pH trigger, and dipeptide (Asp-Asp) between them. The pKa values of 2-nitrophenol groups of 6a-c in liposome are larger than that of hydrophilic compound 9 in an aqueous solution. Absorption spectra indicate that the fields around 2-nitrophenol of 6a-c situated in liposome membranes are more hydrophobic than that of 9 in an aqueous solution, whereas the environments around deprotonated 2-nitrophenolate of 6b and 6c are not so hydrophobic as that of 6a. This means that protonated 2-nitrophenol groups of 6a-c are embedded in bilayer membranes. Deprotonated 2-nitrophenol groups of 6b and 6c must be located in less hydrophobic circumstances, while that of 6a is still embedded in bilayer membranes because of its larger hydrophobicity. Absorption spectra and H-1 NMR spectra respectively suggest that protonated 2-nitrophenol groups of 6a and those of 6c might take face-to-face associations in bilayer membranes.

  DOI：

  10.1021/ja037796x
• 作为产物：
  描述：

  2-硝基-4-氨基苯酚 、 3,3'-(ethane-1,2-diylbis(oxy))dipropanoic acid 在 1-羟基苯并三唑一水物 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以32%的产率得到3-{2-[2-(4-hydroxy-3-nitrophenylcarbamoyl)ethoxy]ethoxy}propionic acid
  参考文献：
  名称：

  Synthesis and Spectroscopic Analysis of Chromophoric Lipids Inducing pH-Dependent Liposome Fusion

  摘要：

  We design novel chromophoric amphiphiles 6a-c, which lead to pH-dependent membrane fusion of egg phosphatidylcholine (eggPC) liposome containing them. Lipids 6a-c comprise double alkyl chains, a single chain with a 2-nitrophenol group as a pH trigger, and dipeptide (Asp-Asp) between them. The pKa values of 2-nitrophenol groups of 6a-c in liposome are larger than that of hydrophilic compound 9 in an aqueous solution. Absorption spectra indicate that the fields around 2-nitrophenol of 6a-c situated in liposome membranes are more hydrophobic than that of 9 in an aqueous solution, whereas the environments around deprotonated 2-nitrophenolate of 6b and 6c are not so hydrophobic as that of 6a. This means that protonated 2-nitrophenol groups of 6a-c are embedded in bilayer membranes. Deprotonated 2-nitrophenol groups of 6b and 6c must be located in less hydrophobic circumstances, while that of 6a is still embedded in bilayer membranes because of its larger hydrophobicity. Absorption spectra and H-1 NMR spectra respectively suggest that protonated 2-nitrophenol groups of 6a and those of 6c might take face-to-face associations in bilayer membranes.

  DOI：

  10.1021/ja037796x