ethyl 2-nitrooxyacetate | 999-17-7

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: ethyl 2-nitrooxyacetate
• 英文别名: nitryloxy-acetic acid ethyl ester；Nitryloxy-essigsaeure-aethylester；Glykolsaeure-aethylester-nitrat；2-Nitryloxy-essigsaeure-aethylester；1-Aethoxycarbonyl-1-nitratomethan；Glycolsaeure-ethylester-nitrat；Acetic acid, (nitrooxy)-, ethyl ester
• CAS: 999-17-7
• 化学式: C₄H₇NO₅
• 分子量: 149.103
• InChiKey: PMCOPORTQICYLN-UHFFFAOYSA-N

物化性质

• 溶解度：
  0.02 M

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-nitrooxyacetate 、 sodium trichloroacetate 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以75%的产率得到ethyl 3,3,3-trichloro-2-hydroxypropanoate
  参考文献：
  名称：

  Synthesis of α-Functionalized Trichloromethylcarbinols

  摘要：

  A new series of alpha-functionalized trichloromethylcarbinols have been synthesized from corresponding alpha-halomethyl ketones, esters, and amides in 48-78% overall yields. Reactivity of nitrates obtained in the first step was dependent on the electron-withdrawing nature of the functional groups, and increases with increasing electron deficiency. Synthetic applications of such trichloromethylcarbinols for the preparation of chloromethyl-alpha-diketones, trichloromethylated dihydrofurans, and enol acetates of alpha-functionalized acid chlorides have been demonstrated. The reaction of these compounds in the Jocic-Reeve reaction was also demonstrated.

  DOI：

  10.1021/acs.joc.5b01547
• 作为产物：
  描述：

  乙醇酸乙酯 在 硫酸 、 硝酸 作用下， 生成 ethyl 2-nitrooxyacetate
  参考文献：
  名称：

  Henry, Annales de Chimie (Cachan, France), 1873, vol. <4>28, p. 424

  摘要：

  DOI：

文献信息

• Nitrocyclopropanes from nitrodiazomethanes. Preparation and reactivity
  作者：P.E. O'Bannon、William P. Dailey

  DOI：10.1016/s0040-4020(01)89052-9

  日期：——

  Nitrodiazo compounds cyclopropanate electron rich alkenes in the presence of rhodium(II) acetate. The yields and diastereoselectivities are dependent on both the alkene and the nitrodiazo precursor. Nitrocyclopropanecarboxylates undergo ring opening, reduction and hydrolysis.

  硝基重氮化合物在乙酸铑（II）的存在下形成环丙酸酯富电子的烯烃。产率和非对映选择性同时取决于烯烃和硝基二偶氮前体。硝基环丙烷羧酸酯经历开环，还原和水解作用。
• Oxidative nucleophilic substitution reaction of alkyl iodides upon treatment with perchlorate and dinitramide anions. Synthesis of alkyl-substituted perchlorates
  作者：N. V. Yashin、E. B. Averina、Yu. K. Grishin、V. B. Rybakov、T. S. Kuznetsova、N. S. Zefirov

  DOI：10.1007/s11172-016-1320-4

  日期：2016.2

  Reactions of oxidative nucleophilic substitution of alkyl iodides with lithium perchlorate and dinitramide were studied. The reactions of alkyl iodides and lithium perchlorate, proceeding in the presence of nitronium tetrafluoroborate as an oxidant, furnished a series of new alkyl perchlorates, including those containing an adamantyl fragment. Spectral properties of alkyl perchlorates were studied

  研究了烷基碘与高氯酸锂和二硝胺的氧化亲核取代反应。在四氟硼酸硝鎓作为氧化剂的存在下，烷基碘和高氯酸锂的反应提供了一系列新的高氯酸烷基酯，包括含有金刚烷基片段的那些。首次详细研究了高氯酸烷基酯的光谱性质。碘乙酸酯和二硝胺锂的氧化亲核取代反应，在用四氟硼酸硝鎓或臭氧处理后进行，导致碘原子被硝酸根阴离子取代。
• Svetlakov,N.V. et al., Journal of Organic Chemistry USSR (English Translation), 1968, vol. 4, # 12, p. 2024 - 2027
  作者：Svetlakov,N.V. et al.

  DOI：——

  日期：——
• Fichter; Steinbuch, Helvetica Chimica Acta, 1943, vol. 26, p. 697
  作者：Fichter、Steinbuch

  DOI：——

  日期：——
• Hammond,G.S. et al., Tetrahedron, Supplement, 1963, vol. 4, p. 177 - 195
  作者：Hammond,G.S. et al.

  DOI：——

  日期：——