2-<2-amino-1-(2-nitrophenyl)ethoxy>ethanol | 172756-76-2

• 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: 2-<2-amino-1-(2-nitrophenyl)ethoxy>ethanol
• 英文别名: 2-[2-Amino-1-(2-nitrophenyl)ethoxy]ethanol
• CAS: 172756-76-2
• 化学式: C₁₀H₁₄N₂O₄
• 分子量: 226.232
• InChiKey: JSBOQLHJDCXEEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-<2-amino-1-(2-nitrophenyl)ethoxy>ethanol 在 碳酸氢钠 、 三乙胺 、 三氟乙酸 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 5.92h， 生成 1-<1-(2-iodoethoxy)-2-isothiocyanatoethyl>-2-nitrobenzene
  参考文献：
  名称：

  Synthesis and Characterization of Photolabile Choline Precursors as Reversible Inhibitors of Cholinesterases:  Release of Choline in the Microsecond Time Range

  摘要：

  Three o-nitrobenzyl ether derivatives of choline (compounds A-C) were synthesized as photolabile cholinesterase inhibitors in order to study the mechanism of choline release from the enzyme active site. The key step of the synthesis was a simple and efficient Lewis acid-catalyzed opening of dioxolane rings derived from o-nitrobenzaldehyde and o-nitroacetophenone. Laser flash photolyses of compounds A-C were analyzed by UV spectroscopy, HPLC, and an enzymatic assay for choline. The quantum yields of photoconversion were determined, and the kinetics of choline release were analyzed by studying the decay of the transient aci-nitro intermediate at 405 nm. The observed rates varied considerably in function of both pH and the substituent at the alpha-benzylic position. Furthermore, we demonstrated that all three compounds possessed reversible inhibitory properties on both purified Torpedo acetylcholinesterase and purified human plasma butyrylcholinesterase. Compound A, O-[1-(2-nitrophenyl)ethyl]choline iodide, which displayed the highest quantum yield (0.27) and the most rapid photolysis rate (6.8 x 10(4) s(-1) at pH 6.5), represents therefore an interesting tool for the study of the fast process of choline release from cholinesterases by time-resolved Laue crystallography.

  DOI：

  10.1021/jo951190c
• 作为产物：
  描述：

  2-(2-硝基苯基)-1,3-二氧戊环 在 硼烷四氢呋喃络合物 、 zinc(II) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 生成 2-<2-amino-1-(2-nitrophenyl)ethoxy>ethanol
  参考文献：
  名称：

  具有光裂解大环接头的位点选择性自旋探针用于测量脂质体组装周围水的动力学

  摘要：

  人们越来越关注水在软物质表面的水合层上的行为，以开发可在水环境中发挥作用的湿材料并增加对复杂生物现象的理解。动态核极化 (DNP) 通过利用电子自旋的磁化增强核自旋的磁化来提高核磁共振 (NMR) 的灵敏度，最近作为一种测量水合水动力学的方法引起了人们的关注。功能性自旋探针的设计有望提供按需测量。在这项研究中，我们报告了原位的结果，使用可光解大环的脂质体周围水的位点选择性测量方法。我们通过光裂解邻硝基苄基醚衍生物成功地测量了同一样品脂质体膜周围两个不同区域的水动力学差异。

  DOI：

  10.1246/bcsj.20220027

文献信息

• Synthesis and Characterization of Photolabile Choline Precursors as Reversible Inhibitors of Cholinesterases:  Release of Choline in the Microsecond Time Range
  作者：Ling Peng、Maurice Goeldner

  DOI：10.1021/jo951190c

  日期：1996.1.1

  Three o-nitrobenzyl ether derivatives of choline (compounds A-C) were synthesized as photolabile cholinesterase inhibitors in order to study the mechanism of choline release from the enzyme active site. The key step of the synthesis was a simple and efficient Lewis acid-catalyzed opening of dioxolane rings derived from o-nitrobenzaldehyde and o-nitroacetophenone. Laser flash photolyses of compounds A-C were analyzed by UV spectroscopy, HPLC, and an enzymatic assay for choline. The quantum yields of photoconversion were determined, and the kinetics of choline release were analyzed by studying the decay of the transient aci-nitro intermediate at 405 nm. The observed rates varied considerably in function of both pH and the substituent at the alpha-benzylic position. Furthermore, we demonstrated that all three compounds possessed reversible inhibitory properties on both purified Torpedo acetylcholinesterase and purified human plasma butyrylcholinesterase. Compound A, O-[1-(2-nitrophenyl)ethyl]choline iodide, which displayed the highest quantum yield (0.27) and the most rapid photolysis rate (6.8 x 10(4) s(-1) at pH 6.5), represents therefore an interesting tool for the study of the fast process of choline release from cholinesterases by time-resolved Laue crystallography.
• Site-Selective Spin-Probe with a Photocleavable Macrocyclic Linker for Measuring the Dynamics of Water Surrounding a Liposomal Assembly
  作者：Gyeorye Lee、Yoshiyuki Kageyama、Sadamu Takeda

  DOI：10.1246/bcsj.20220027

  日期：2022.6.15

  behavior of water on the hydration layer of a soft matter surface in order to develop wet materials that can function in an aqueous environment and to increase the understanding of complex biological phenomena. Dynamic nuclear polarization (DNP), which increases the sensitivity of nuclear magnetic resonance (NMR) by enhancing the magnetization of nuclear spin with the magnetization of electron spin, has recently

  人们越来越关注水在软物质表面的水合层上的行为，以开发可在水环境中发挥作用的湿材料并增加对复杂生物现象的理解。动态核极化 (DNP) 通过利用电子自旋的磁化增强核自旋的磁化来提高核磁共振 (NMR) 的灵敏度，最近作为一种测量水合水动力学的方法引起了人们的关注。功能性自旋探针的设计有望提供按需测量。在这项研究中，我们报告了原位的结果，使用可光解大环的脂质体周围水的位点选择性测量方法。我们通过光裂解邻硝基苄基醚衍生物成功地测量了同一样品脂质体膜周围两个不同区域的水动力学差异。