3-ethoxycarbonyl-4,5-dihydroisoxazole-5-carboxylic acid | 142074-51-9

• 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: 3-ethoxycarbonyl-4,5-dihydroisoxazole-5-carboxylic acid
• 英文别名: 3-Ethoxycarbonyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid
• CAS: 142074-51-9
• 化学式: C₇H₉NO₅
• 分子量: 187.152
• InChiKey: BMQTXLVNWGAQMM-UHFFFAOYSA-N

物化性质

• 沸点：
  326.7±52.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  85.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-ethoxycarbonyl-4,5-dihydroisoxazole-5-carboxylic acid 在 4-二甲氨基吡啶 、 三甲基铝 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-N-benzyl-5-N-(2-methylpropyl)-4,5-dihydro-1,2-oxazole-3,5-dicarboxamide
  参考文献：
  名称：

  1,3-Cycloaddition of nitrile oxides in ionic liquids. An easier route to 3-carboxy isoxazolines, potential constrained glutamic acid analogues

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(03)01195-x
• 作为产物：
  描述：

  5-benzyl 3-ethyl 4,5-dihydroisoxazole-3,5-dicarboxylate 在 palladium on activated charcoal 氢气 、 乙酸乙酯 作用下， 以 氯仿 为溶剂， 以96%的产率得到3-ethoxycarbonyl-4,5-dihydroisoxazole-5-carboxylic acid
  参考文献：
  名称：

  1,3-Cycloaddition of nitrile oxides in ionic liquids. An easier route to 3-carboxy isoxazolines, potential constrained glutamic acid analogues

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(03)01195-x

文献信息

• Selective transformation of nitriles into amides and carboxylic acids by an immobilized nitrilase
  作者：Norbert Klempier、Anna de Raadt、Kurt Faber、Herfried Griengl

  DOI：10.1016/s0040-4039(00)92623-6

  日期：1991.1

  Using an immobilized nitrilase from Rhodococcus sp. mild and selective hydrolysis of nitriles can be achieved even in the presence of acid or base sensitive groups under neutral conditions. This method is applicable to a broad range of substrates as exemplified by aliphatic, alicyclic, heterocyclic and carbohydrate type nitriles.

  使用来自红球菌属的固定化腈水解酶。即使在中性条件下存在酸或碱敏感基团，也可以实现腈的温和选择性水解。该方法适用于各种底物，例如脂族，脂环族，杂环和碳水化合物类腈。
• Conjugate Addition versus Cycloaddition/Condensation of Nitro Compounds in Water: Selectivity, Acid-Base Catalysis, and Induction Period
  作者：Luca Guideri、Francesco De Sarlo、Fabrizio Machetti

  DOI：10.1002/chem.201202698

  日期：2013.1.7

  react in water as in chloroform with electron‐deficient dipolarophiles to give condensation or conjugate addition products under base catalysis. In general, high selectivity towards condensation is observed in water, with shorter induction periods than in chloroform. In water, condensations slowly occur even without base; kinetic profiles evidence the catalytic effect of the base, which should be related

  硝基乙酸盐和硝基乙酰胺在水中（如氯仿中）与缺电子的双极性亲和剂反应，在碱催化下生成缩合或共轭加成产物。通常，在水中观察到对缩合的高选择性，诱导时间比在氯仿中短。在水中，即使没有碱，凝结也会缓慢发生。动力学曲线证明了碱的催化作用，这与转化为互变异构体硝酸有关。水中的冷凝可方便地获得带有各种官能团（包括铵，羧基和羧酰胺）的异恶唑衍生物。
• Klempier, Norbert; Raadt, Anna de; Griengl, Herfried, Journal of Heterocyclic Chemistry, 1992, vol. 29, # 1, p. 93 - 95
  作者：Klempier, Norbert、Raadt, Anna de、Griengl, Herfried、Heinisch, Gottfried

  DOI：——

  日期：——
• 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.

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