methyl 5-methyl-3-nitro-4,5-dihydroisoxazole-5-carboxylate | 5923-49-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 亚胺内酰胺
• 英文名称: methyl 5-methyl-3-nitro-4,5-dihydroisoxazole-5-carboxylate
• 英文别名: methyl 3-nitro-4,5-dihydroisoxazole-5-carboxylate；5-methoxycarbonyl-3-nitroisoxazoline；3-Nitro-5-carbomethoxyisoxazolin；5-Carbomethoxy-3-nitro-Δ²-isoxazolin；3-nitro-4,5-dihydro-isoxazole-5-carboxylic acid methyl ester；Methyl 3-nitro-4,5-dihydro-1,2-oxazole-5-carboxylate；methyl 3-nitro-4,5-dihydro-1,2-oxazole-5-carboxylate
• CAS: 5923-49-9
• 化学式: C₅H₆N₂O₅
• 分子量: 174.113
• InChiKey: NSVNGUKLPWVYNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  93.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-hydroxy-3a-nitro-tetrahydro-isoxazolo[2,3-b]isoxazole-2-carboxylic acid methyl ester 以 水 、 苯 为溶剂， 生成 methyl 5-methyl-3-nitro-4,5-dihydroisoxazole-5-carboxylate
  参考文献：
  名称：

  Tartakovskii,V.A. et al., Doklady Chemistry, 1966, vol. 167, p. 406 - 409

  摘要：

  DOI：

文献信息

• Ionic liquid-promoted [3+2]-cycloaddition reactions of nitroformonitrile oxide generated by the cycloreversion of dinitrofuroxan
  作者：Leonid L. Fershtat、Igor V. Ovchinnikov、Nina N. Makhova

  DOI：10.1016/j.tetlet.2014.02.112

  日期：2014.4

  synthesis of 3-nitroisoxazoles and 3-nitroisoxazolines based on the [3+2]-cycloaddition of nitroformonitrile oxide (NFNO), generated by the cycloreversion of dinitrofuroxan (DNFO), to acetylene and ethylene derivatives, under ionic liquid catalysis is developed. The approach is of a general nature and applicable to cycloaddition reactions with other dipolarophiles.

  在离子液体下，基于由二硝基呋喃（DNFO）环还原为乙炔和乙烯衍生物而生成的硝基甲腈氧化物（NFNO）的[3 + 2]-环加成反应，合成3-硝基异恶唑和3-硝基异恶唑啉的新方法催化作用得到发展。该方法具有一般性质，适用于与其他偶极亲和剂的环加成反应。
• Dinitrofuroxan cycloreversion as a novel general approach for the synthesis of nitroazoles
  作者：L. L. Fershtat、D. V. Khakimov、N. N. Makhova

  DOI：10.1007/s11172-015-0878-6

  日期：2015.2

  A novel general approach towards various nitroazoles via tandem process involving dinitrofuroxan cycloreversion followed by [3+2] cycloaddition of generated in situ nitroformonitrile oxide is developed. The reaction is promoted by addition of catalytic amounts of ionic liquids. Plausible mechanisms of the described processes based on quantum chemical calculations are proposed.

  开发了一种通过涉及二硝基呋咱环反转后跟生成的当场硝基亚甲硝基氧化物的[3+2]环加成串联过程来合成各种硝基唑类的新型通用方法。反应通过加入催化量的离子液体来促进。基于量子化学计算，提出了所描述过程的可能机制。
• Application of a Thermal β-Elimination Reaction to<i>N</i>-Alkoxy-3,3-dinitro­isoxazolidines: Synthesis of 3-Nitroisoxazolines
  作者：Tamara S. Kuznetsova、Olga A. Ivanova、Ekaterina M. Budynina、Elena B. Averina、Nikolai S. Zefirov

  DOI：10.1055/s-2006-926312

  日期：——

  A facile general method has been developed for the synthesis of 5-substituted 3-nitroisoxazolines by the application of a thermal β-elimination reaction to N-alkoxy-3,3-dinitroisoxazolidines in chlorobenzene.

  已经开发出一种简便的一般方法，通过在氯苯中对N-烷氧基-3,3-二硝基异噁唑啉进行热β-消除反应，合成5取代的3-硝基异噁唑啉。
• O-methyl ether of dinitromethane in the reaction of 1,3-dipolar cycloaddition
  作者：V. A. Tartakovskii、I. E. Chlenov、N. S. Morozova、S. S. Novikov

  DOI：10.1007/bf00856078

  日期：1966.2