2-[1-(2-硝基苯基)乙氧基]乙醇 | 172756-72-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[1-(2-硝基苯基)乙氧基]乙醇
• 英文名称: 2-<1-(2-nitrophenyl)ethoxy>ethanol
• 英文别名: 2-[1-(2-nitrophenyl)ethoxy]ethanol；Ethanol, 2-[1-(2-nitrophenyl)ethoxy]-
• CAS: 172756-72-8
• 化学式: C₁₀H₁₃NO₄
• 分子量: 211.218
• InChiKey: IXRAKQMCLHJPAU-UHFFFAOYSA-N

物化性质

• 沸点：
  356.1±22.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[1-(2-硝基苯基)乙氧基]乙醇 在 四氮唑 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  1-(2-硝基苯基)乙基醚的光解涉及两个平行途径，产物释放受常见半缩醛中间体分解的限速

  摘要：

  几种衍生自脂肪醇的 1-(2-硝基苯基)乙基醚的闪光光解的时间分辨 FTIR 光谱研究表明，在反应过程中形成了长寿命的半缩醛中间体。该中间体的分解是产品发布的速率限制。通过时间分辨 FTIR 和 UV-vis 光谱的组合，对这些化合物之一（2-[1-（2-硝基苯基）乙氧基]乙基磷酸酯，9）进行了详细研究。此外，产品研究证实了对预期酒精、2-羟乙基甲基磷酸酯和 2-亚硝基苯乙酮副产品的清洁光解分解。在 pH 7.0、1 摄氏度下，产品释放的速率常数为 0.11 s(-1)，比光化学生成的 aci-nitro 中间体 (pH 7.0, 2) 衰减的 5020 s(-1) 速率常数慢得多摄氏度）。时间分辨 UV-vis 测量表明，半缩醛中间体由两种竞争途径形成，具有快速（约 80% 的反应通量）和慢速（约 20% 的通量）组分。只有较小的、较慢的路径负责观察到的 aci-nitro 衰变过程。这些竞争反应是在反应势垒的半经验

  DOI：

  10.1021/ja034354c
• 作为产物：
  描述：

  2-methyl-2-(2-nitrophenyl)-1,3-dioxolane 在 四氯化钛 、 sodium cyanoborohydride 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以95%的产率得到2-[1-(2-硝基苯基)乙氧基]乙醇
  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

• Photolytic Cleavage of 1-(2-Nitrophenyl)ethyl Ethers Involves Two Parallel Pathways and Product Release Is Rate-Limited by Decomposition of a Common Hemiacetal Intermediate
  作者：John E. T. Corrie、Andreas Barth、V. Ranjit N. Munasinghe、David R. Trentham、Michael C. Hutter

  DOI：10.1021/ja034354c

  日期：2003.7.1

  responsible for the observed aci-nitro decay process. These competing reactions are interpreted with the aid of semiempirical PM3 calculations of reaction barriers. Furthermore, AMSOL calculations indicate that the pK(a) of the nitronic acid isomer formed by photolysis is likely to determine partition into the alternate paths. These unusual results appear to be general for 1-(2-nitrophenyl)ethyl ethers and

  几种衍生自脂肪醇的 1-(2-硝基苯基)乙基醚的闪光光解的时间分辨 FTIR 光谱研究表明，在反应过程中形成了长寿命的半缩醛中间体。该中间体的分解是产品发布的速率限制。通过时间分辨 FTIR 和 UV-vis 光谱的组合，对这些化合物之一（2-[1-（2-硝基苯基）乙氧基]乙基磷酸酯，9）进行了详细研究。此外，产品研究证实了对预期酒精、2-羟乙基甲基磷酸酯和 2-亚硝基苯乙酮副产品的清洁光解分解。在 pH 7.0、1 摄氏度下，产品释放的速率常数为 0.11 s(-1)，比光化学生成的 aci-nitro 中间体 (pH 7.0, 2) 衰减的 5020 s(-1) 速率常数慢得多摄氏度）。时间分辨 UV-vis 测量表明，半缩醛中间体由两种竞争途径形成，具有快速（约 80% 的反应通量）和慢速（约 20% 的通量）组分。只有较小的、较慢的路径负责观察到的 aci-nitro 衰变过程。这些竞争反应是在反应势垒的半经验
• 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.