(2-nitrophenyl)<2-<(trimethylsilyl)oxy>ethoxy>acetonitrile | 172756-75-1

• 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: (2-nitrophenyl)<2-<(trimethylsilyl)oxy>ethoxy>acetonitrile
• 英文别名: 2-(2-Nitrophenyl)-2-(2-trimethylsilyloxyethoxy)acetonitrile
• CAS: 172756-75-1
• 化学式: C₁₃H₁₈N₂O₄Si
• 分子量: 294.382
• InChiKey: FOZZKFUTVIZWHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-nitrophenyl)<2-<(trimethylsilyl)oxy>ethoxy>acetonitrile 在 盐酸 、 硼烷四氢呋喃络合物 、 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 9.92h， 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：

  三甲基氰硅烷 、 2-(2-硝基苯基)-1,3-二氧戊环 在 zinc(II) iodide 作用下， 反应 0.25h， 以80%的产率得到(2-nitrophenyl)<2-<(trimethylsilyl)oxy>ethoxy>acetonitrile
  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

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.