4-ethoxycarbonyl-3-methylfuroxan | 37895-43-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-ethoxycarbonyl-3-methylfuroxan
• 英文别名: 3-methyl-4-carbethoxyfuroxane；4-methyl-5-oxy-furazan-3-carboxylic acid ethyl ester；3-Methyl-4-ethoxycarbonyl-1,2,5-oxadiazol-2-oxid；3-Methyl-4-furoxancarbonsaeureethyleastewr；3-Methyl-4-furoxancarbonsaeureethylester；Ethyl 4-methyl-5-oxido-1,2,5-oxadiazol-5-ium-3-carboxylate
• CAS: 37895-43-5
• 化学式: C₆H₈N₂O₄
• 分子量: 172.141
• InChiKey: WZRFXHNGQUJXSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  67-71 °C(Press: 0.5 Torr)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  77.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-ethoxycarbonyl-3-methylfuroxan 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以85%的产率得到4-(hydroxymethyl)-3-methylfuroxan
  参考文献：
  名称：

  ?-hydroaxyalkyl(benzyl)furozans and ?-hydroxyalkyl(benzyl)furoxans synthesis and reactivity

  摘要：

  A general,and simple preparative method for the synthesis of alpha-hydroxyalkyl(benzyI)furazan and -furoxan derivatives is proposed. The method involves reduction of acyl or ethoxycarbonyl substituents in these heterocyclic compounds with NaBH4 in ethanol. Based on the alcohols thus prepared, a number of previously unknown functional derivatives (alpha-nitroxyalkyl-,alpha-haloalkyl-, and alpha-azidoalkylfurazans and -furoxans) have been synthesized.

  DOI：

  10.1007/bf01431809
• 作为产物：
  描述：

  ethyl 2,3-bis(hydroxyimino)butanoate 在 硝酸 作用下， 生成 4-ethoxycarbonyl-3-methylfuroxan
  参考文献：
  名称：

  Gasco,A. et al., Journal of Heterocyclic Chemistry, 1972, vol. 9, p. 577 - 580

  摘要：

  DOI：

文献信息

• A Facile and Versatile Synthesis of Energetic Furazan‐Functionalized 5‐Nitroimino‐1,2,4‐Triazoles
  作者：Zhen Xu、Guangbin Cheng、Hongwei Yang、Xuehai Ju、Ping Yin、Jiaheng Zhang、Jean'ne M. Shreeve

  DOI：10.1002/anie.201701659

  日期：2017.5.15

  An analogue‐oriented synthetic route for the formulation of furazan‐functionalized 5‐nitroimino‐1,2,4‐triazoles has been explored. The process was found to be straightforward, high yielding, and highly efficient, and scalable. Nine compounds were synthesized and the physicochemical and energetic properties, including density, thermal stability, and sensitivity, were investigated, as well as the energetic

  探索了以类似物为导向的合成路线，用于制备呋喃山官能化的5-硝基亚氨基-1,2,4-三唑。发现该过程是直接的，高产量的，高效的和可扩展的。合成了9种化合物，并使用EXPLO5代码研究了包括密度，热稳定性和敏感性在内的物理化学和能量特性，以及能量性能（例如，爆轰速度和爆轰压力）。在这些新的材料，化合物4 - 6和11具有高密度，可接受的敏感性和良好的爆轰性能，并由此证明了潜在的应用作为新的辅助炸药。
• Oxidation of <i>o</i>-dioxime by (diacetoxyiodo)benzene: green and mild access to furoxans
  作者：Qi Zhang、Cheng Zhao、Xun Zhang、Chunlin He、Siping Pang

  DOI：10.1039/d1nj05510k

  日期：——

  widely used in the field of high energy density materials because of its excellent properties such as high density, high standard enthalpy of formation and high nitrogen content. However, its existing synthesis methods are still restricted by the problems of difficult substrate preparation and manual handling of hazardous reagents. Herein, we disclosed a mild oxidation strategy to efficiently obtain

  Furoxan因其高密度、高标准生成焓和高含氮量等优异性能而被广泛应用于高能密度材料领域。然而，其现有的合成方法仍受到底物制备困难和危险试剂人工操作等问题的限制。在这里，我们公开了一种温和的氧化策略，以从容易获得的邻二肟底物开始有效地获得呋喃衍生物。该反应具有高官能团耐受性和易于放大的特点，对特定的非对称o具有优异的区域选择性-二肟。该方法大大降低了安全风险，简化了操作流程，意味着可以轻松获取多样化的呋喃衍生物，为呋喃衍生物的广泛应用铺平了道路。
• The First Synthesis of Furoxan and 1,3,4-Oxadiazole Ring Ensembles
  作者：Aleksey O. Finogenov、Alexander S. Kulikov、Margarita A. Epishina、Igor V. Ovchinnikov、Yu. V. Nelyubina、Nina N. Makhova

  DOI：10.1002/jhet.1048

  日期：2013.1

  Previously unknown furoxan and 1,3,4‐oxadiazole ring ensembles incorporating two, three, and five furoxan and 1,3,4‐oxadiazole rings in different combinations were for the first time synthesized from accessible azides and hydrazides of furoxancarboxylic acids. An interdependence of furoxan and 1,3,4‐oxadiazole rings on their geometric parameters was revealed by the X‐ray diffraction method.

  首次未知的呋喃喃和1,2,3,4-恶二唑环合体以不同组合结合了两个，三个和五个呋喃烷和1,3,4-恶二唑环，是由呋喃甲酸的可叠氮化物和酰肼合成的。X射线衍射法揭示了呋喃烷和1,3,4-恶二唑环在其几何参数上的相互依赖性。
• α,β-Unsaturated Carboxylic Acid Derivatives. XV. The Reaction of Ethyl 3-Nitro-2-alkenoate with Bromine Azide or Bromine, and Transformations of the Products
  作者：Chung-gi Shin、Yasuchika Yonezawa、Kaoru Suzuki、Juji Yoshimura

  DOI：10.1246/bcsj.51.2614

  日期：1978.9

  The reaction of ethyl (Z)-3-nitro-2-alkenoate (1) with one or two equivalents of bromine azide gave a one-to-one mixture of ethyl (E)-2-azido-3-nitro-2-alkenoate (3) and 4-ethoxycarbonyl-1,2,5-oxadiazole 2-oxide (5), or ethyl 3-bromo-2,2-diazido-3-nitroalkanoate (6), respectively, and the subsequent thermal and photochemical reactions of (E)-3 gave 2-ethoxycarbonyl-3-nitro-l-azirine, together with

  (Z)-3-硝基-2-链烯酸乙酯 (1) 与一当量或两当量的溴叠氮化物反应得到 (E)-2-叠氮基-3-硝基-2-乙酯的一对一混合物链烯酸酯 (3) 和 4-乙氧基羰基-1,2,5-恶二唑 2-氧化物 (5) 或 3-溴-2,2-二叠氮基-3-硝基链烷酸乙酯 (6)，以及随后的热和光化学(E)-3 的反应得到 2-乙氧羰基-3-硝基-1-氮丙啶，以及少量的 5。将溴加到 1 中，随后从产物中消除溴化氢，仅得到(Z)-2-溴衍生物(9)。考察了膦酸二乙酯对 6 和 9 的还原反应，并讨论了反应机理。
• ?-hydroaxyalkyl(benzyl)furozans and ?-hydroxyalkyl(benzyl)furoxans synthesis and reactivity
  作者：A. N. Blinnikov、S. Kulikov、N. N. Makhova、L. I. Khmel'nitskii

  DOI：10.1007/bf01431809

  日期：1996.7

  A general,and simple preparative method for the synthesis of alpha-hydroxyalkyl(benzyI)furazan and -furoxan derivatives is proposed. The method involves reduction of acyl or ethoxycarbonyl substituents in these heterocyclic compounds with NaBH4 in ethanol. Based on the alcohols thus prepared, a number of previously unknown functional derivatives (alpha-nitroxyalkyl-,alpha-haloalkyl-, and alpha-azidoalkylfurazans and -furoxans) have been synthesized.