1-(5-硝基-1,2-恶唑-3-基)乙酮 | 340014-77-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 1-(5-硝基-1,2-恶唑-3-基)乙酮
• 中文别名: 苯甲酰胺，4-乙基-N，N-二甲基-3-硝基-(9CI)
• 英文名称: 1-(5-nitroisoxazol-3-yl)ethanone
• 英文别名: 3-acetyl-5-nitroisoxazole；1-(5-nitro-1,2-oxazol-3-yl)ethanone
• CAS: 340014-77-9
• 化学式: C₅H₄N₂O₄
• mdl: MFCD01445282
• 分子量: 156.098
• InChiKey: AUAKIVSEIKDQPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  88.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(5-硝基-1,2-恶唑-3-基)乙酮 在 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以75%的产率得到1-(5-aminoisoxazol-3-yl)ethanone
  参考文献：
  名称：

  Chemoselective Reduction of Functionalized 5-Nitroisoxazoles: Synthesis of 5-Amino- and 5-[Hydroxy(tetrahydrofuran-2-yl)amino]isoxazoles

  摘要：

  Reduction by using SnCl2 of easily accessible 5-nitroisoxazoles substituted with an electron-withdrawing group (EWG) has been studied. Whereas the reaction in ethanol yielded 5-aminoisoxazoles, performing the reaction in tetrahydrofuran gave previously unknown 5-[hydroxy(tetrahydrofuran-2-yl)amino]isoxazoles. Both reduction procedures were optimized to afford the corresponding products in good to excellent yields. Some mechanistic details concerning the inclusion of the tetrahydrofuranyl moiety into the reaction product are discussed

  DOI：

  10.1055/s-0033-1340827
• 作为产物：
  描述：

  5,5,5-trinitropentan-2-one 在 盐酸 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以26.7%的产率得到1-(5-硝基-1,2-恶唑-3-基)乙酮
  参考文献：
  名称：

  Synthesis of 3-acyl-5-nitroisoxazoles on the base of geminal trinitro- and chlorodinitro-substituted pentan-2-one or 2-oximino-1-phenylbutan-1-one

  摘要：

  通过在 100 °C 下在 DMF 中用氯化锂加热 5,5,5-三硝基-2-戊酮，以及在有机溶剂中加热 5,5,5-三硝基、5-氯-5,5-二硝基-2-戊酮或 4,4,4-三硝基和 4-氯-4,4-二硝基-1-苯基-1-丁酮的氧亚氨基衍生物，合成了 3-酰基-5-硝基异噁唑。

  DOI：

  10.1007/s11172-009-0299-5

文献信息

• Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 5-Nitroisoxazoles
  作者：Yulia A. Volkova、Elena B. Averina、Dmitry A. Vasilenko、Kseniya N. Sedenkova、Yuri K. Grishin、Per Bruheim、Tamara S. Kuznetsova、Nikolai S. Zefirov

  DOI：10.1021/acs.joc.8b03086

  日期：2019.3.15

  A novel reaction of tetranitromethane with electrophilic alkenes in the presence of triethylamine affording substituted 5-nitroisoxazoles is described. Triethylamine reacts with tetranitromethane to generate N-nitrotriethylammonium and trinitromethanide. This process provides the heterocyclization of electrophilic alkenes. A variety of α,β-unsaturated aldehydes, ketones, esters, amides, phosphonates

  描述了在三乙胺存在下四硝基甲烷与亲电烯烃的新型反应，提供了取代的5-硝基异恶唑。三乙胺与四硝基甲烷反应生成N-硝基三乙铵和三硝基甲烷。该过程提供了亲电烯烃的杂环化。各种α，β-不饱和醛，酮，酯，酰胺，膦酸酯，硝基和硫化合物参与了杂环化反应，并以良好或高收率获得了多种官能化的5-硝基异恶唑。讨论了反应的范围和局限性以及机理建议。
• 5-Nitroisoxazoles in S_NAr reactions: access to polysubstituted isoxazole derivatives
  作者：Dmitry A. Vasilenko、Sevastian E. Dronov、Dzianis U. Parfiryeu、Kirill S. Sadovnikov、Kseniya N. Sedenkova、Yuri K. Grishin、Victor B. Rybakov、Tamara S. Kuznetsova、Elena B. Averina

  DOI：10.1039/d1ob00816a

  日期：——

  functionalization of the isoxazole ring via the reactions of aromatic nucleophilic substitution of the nitro group with various nucleophiles has been elaborated. The method features excellent chemical yields, easy operability of the reaction, mild reaction conditions and a broad scope of both 5-nitroisoxazoles and nucleophiles. A synthetic approach to 3,5- and 3,4,5-substituted isoxazoles via the sequential

  已经详细阐述了通过硝基的芳香亲核取代与各种亲核试剂的反应对异恶唑环进行直接功能化的有效方案。该方法具有优异的化学收率、反应易于操作、反应条件温和、5-硝基异恶唑和亲核试剂适用范围广等特点。基于 3,5-二硝基异恶唑与亲核试剂反应的优异区域选择性，开发了一种通过异恶唑环的顺序官能化合成3,5-和 3,4,5-取代异恶唑的方法。
• Chemoselective Reduction of Functionalized 5-Nitroisoxazoles: Synthesis of 5-Amino- and 5-[Hydroxy(tetrahydrofuran-2-yl)amino]isoxazoles
  作者：Elena Averina、Dmitry Vasilenko、Yuri Samoilichenko、Yuri Grishin、Victor Rybakov、Tamara Kuznetsova、Nikolay Zefirov

  DOI：10.1055/s-0033-1340827

  日期：——

  Reduction by using SnCl2 of easily accessible 5-nitroisoxazoles substituted with an electron-withdrawing group (EWG) has been studied. Whereas the reaction in ethanol yielded 5-aminoisoxazoles, performing the reaction in tetrahydrofuran gave previously unknown 5-[hydroxy(tetrahydrofuran-2-yl)amino]isoxazoles. Both reduction procedures were optimized to afford the corresponding products in good to excellent yields. Some mechanistic details concerning the inclusion of the tetrahydrofuranyl moiety into the reaction product are discussed
• Synthesis of 3-acyl-5-nitroisoxazoles on the base of geminal trinitro- and chlorodinitro-substituted pentan-2-one or 2-oximino-1-phenylbutan-1-one
  作者：G. Kh. Khisamutdinov、N. M. Lyapin、V. G. Nikitin、V. I. Slovetskii、A. A. Fainzil’berg

  DOI：10.1007/s11172-009-0299-5

  日期：2009.10

  3-Acyl-5-nitroisoxazoles were synthesized by heating 5,5,5-trinitropentan-2-one with LiCl in DMF at 100 °C as well as by heating oximino derivatives of 5,5,5-trinitro-, 5-chloro-5,5-dinitropentan-2-one or 4,4,4-trinitro- and 4-chloro-4,4-dinitro-1-phenylbutan-1-one in organic solvents.

  通过在 100 °C 下在 DMF 中用氯化锂加热 5,5,5-三硝基-2-戊酮，以及在有机溶剂中加热 5,5,5-三硝基、5-氯-5,5-二硝基-2-戊酮或 4,4,4-三硝基和 4-氯-4,4-二硝基-1-苯基-1-丁酮的氧亚氨基衍生物，合成了 3-酰基-5-硝基异噁唑。