5-acetoxy-4,5-dihydroisoxazole-3-carboxylic acid ethyl ester | 25742-60-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-acetoxy-4,5-dihydroisoxazole-3-carboxylic acid ethyl ester
• 英文别名: ethyl 5-acetoxy-4,5-dihydro-3-isoxazolecarboxylate；5-acetoxy-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester；Ethyl 5-acetyloxy-4,5-dihydro-1,2-oxazole-3-carboxylate
• CAS: 25742-60-3
• 化学式: C₈H₁₁NO₅
• 分子量: 201.179
• InChiKey: CIXDFCXIUAGMBU-UHFFFAOYSA-N

物化性质

• 沸点：
  257.7±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  74.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙酸乙烯酯 、 ethyl 2-(hydroxyimino)acetate 在 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 以61%的产率得到5-acetoxy-4,5-dihydroisoxazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  六硝基乙酸铵 (IV) 氧化肟衍生物生成腈氧化物

  摘要：

  芳香族和脂肪族腈氧化物是由 α-羟基亚氨基羧酸与六硝酸铵 (IV) 氧化生成的。它们与烯属和炔属的偶极亲和物反应，以良好的产率得到相应的环加成产物。α-氧代醛肟的氧化也提供了 α-氧代腈氧化物。

  DOI：

  10.1246/bcsj.72.2277

文献信息

• Studies in isoxazole chemistry. II. Isoxazoles from the Δ²-isoxazolin-5-ols and their acetates
  作者：R. G. Micetich

  DOI：10.1139/v70-075

  日期：1970.2.1

  Various 3-substituted-5-acetoxy-Δ2-isoxazolines were made by the 1,3-dipolar cycloaddition of nitrile oxides to vinyl acetate or isopropenyl acetate. These compounds were readily converted in high yield to 3-substituted isoxazoles or 3-substituted-5-methylisoxazoles respectively, on heating. Treatment of the 3-substituted-5-acetoxy-Δ2-isoxazolines with sodium hydroxide in methanol gave rise to the

  通过腈氧化物与乙酸乙烯酯或乙酸异丙烯酯的 1,3-偶极环加成反应制备了各种 3-取代-5-乙酰氧基-Δ2-异恶唑啉。这些化合物在加热时很容易以高产率分别转化为 3-取代的异恶唑或 3-取代的 5-甲基异恶唑。在甲醇中用氢氧化钠处理 3-取代-5-乙酰氧基-Δ2-异恶唑啉在酸化后产生稳定的 Δ2-异恶唑啉-5-醇。这些化合物也可以通过单独加热或在亚硫酰氯的存在下更好地转化为 3-取代的异恶唑。讨论了这些化合物的核磁共振谱。
• Dehydrochlorination of hydroximic acid chlorides by the use of organotin compounds: an application for synthesis of isoxazolines and isoxazoles
  作者：Osamu Moriya、Yoshikiyo Urata、Takeshi Endo

  DOI：10.1039/c39910000017

  日期：——

  The reactions of hydroximic acid chlorides and organotin compounds such as bis(tributyltin) oxide or tetraphenyltin, whereby nitrile oxides are generated effectively, are applied to the preparations of isoxazolines and isoxazoles via[3 + 2] dipolar cycloaddition.

  氢氧酰氯与有机锡化合物（例如二（三丁基锡）氧化物或四苯基锡）的反应可通过[3 + 2]双极性环加成反应将异丁腈有效地用于制备异恶唑啉和异恶唑。
• A New Route to Nitrile Oxides from Primary Alkylhalides for <i>in situ</i> Dipolar Cycloadditions
  作者：Dilipkumar Maiti、Pranab K. Bhattacharya

  DOI：10.1055/s-1998-1669

  日期：1998.4

  A new route to nitrile oxide preparation from primary alkylbromide, chloride, nitrite and their cycloadditions with olefins to form isoxazolines in a single pot are described.

  该论文描述了一条从伯烷基溴化物、氯化物和亚硝酸盐制备氧化腈的新路线，以及它们与烯烃发生环化反应生成异恶唑的过程。
• 1,3-Cycloaddition of nitrile oxides in ionic liquids. An easier route to 3-carboxy isoxazolines, potential constrained glutamic acid analogues
  作者：Dario Conti、Manuela Rodriquez、Alessandro Sega、Maurizio Taddei

  DOI：10.1016/s0040-4039(03)01195-x

  日期：2003.7

  Several improvements in the cycloaddition of carboethoxyformonitrile oxide (CEFNO) with different alkenes are observed in the ionic liquids [bmim][BF4] and [bmim][PF6]. The possibility of obtaining good yields of the corresponding isoxazolines opens the way towards parallel collections of glutamic acid (Glu) analogues. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Magtrieve™ (CrO2) and MnO2 mediated oxidation of aldoximes: studying the reaction course
  作者：Sandeep Bhosale、Santosh Kurhade、Samir Vyas、Venkata P. Palle、Debnath Bhuniya

  DOI：10.1016/j.tet.2010.10.029

  日期：2010.12

  Magtrieve (TM) (CrO2) and MnO2 mediated oxidation of aldoximes to nitrile oxides were studied in details. In presence of external radical source, TEMPO, these reagents did not furnish nitrile oxides, instead favoured deoximation to aldehydes. A common trend of deoximation was established from electronically tuned aldoximes, which is: aliphatic>aromatic>aldoximes with strong electron-withdrawing group, though the extent of deoximation was less in case of CrO2. Above effects were not observed with chloramine-T and diacetoxyiodobenzene, reagents known to produce nitrile oxides via hydroximoyl halide or equivalent ionic intermediates. A putative reaction mechanism is proposed for MO2 (M=Cr, Mn) mediated oxidation of aldoximes through formation of a nitroso-oxime tautomeric pair. Formation of nitrile oxide is possibly occurred from the oxime tautomer via a sigma-type iminoxy radical intermediate. The deoximation process, dominating in presence of external radical environment, is explained following decomposition of the nitroso tautomer. (C) 2010 Elsevier Ltd. All rights reserved.