5,5’-dihydroxymethyl-3,3’-bis-isoxazole | 108129-57-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5,5’-dihydroxymethyl-3,3’-bis-isoxazole
• 英文别名: [3-[5-(Hydroxymethyl)-1,2-oxazol-3-yl]-1,2-oxazol-5-yl]methanol；[3-[5-(hydroxymethyl)-1,2-oxazol-3-yl]-1,2-oxazol-5-yl]methanol
• CAS: 108129-57-3
• 化学式: C₈H₈N₂O₄
• 分子量: 196.163
• InChiKey: MUJZNZLGVWMDMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  92.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,5’-dihydroxymethyl-3,3’-bis-isoxazole 在 硝酸 作用下， 反应 4.0h， 以92%的产率得到3,3’-bis-isoxazole-5,5’-bis-methylene dinitrate
  参考文献：
  名称：

  双异恶唑双亚甲基精酸盐的合成：一种潜在的硝酸盐增塑剂和熔体稳定的高能​​材料。

  摘要：

  描述了3,3'-双-异恶唑-5,5'-双亚甲基二硝酸酯的有效和可扩展合成及其能量性质。该材料具有良好的敏感性。高能特性表明它既可以作为可熔铸的二次炸药，又可以作为推进剂增塑剂。

  DOI：

  10.1002/cplu.201600470
• 作为产物：
  描述：

  5,5'-bis-tetrahydropyran-2-yloximethyl-[3,3']biisoxazolyl 在 盐酸 作用下， 生成 5,5’-dihydroxymethyl-3,3’-bis-isoxazole
  参考文献：
  名称：

  Gaudiano et al., Gazzetta Chimica Italiana, 1957, vol. 87, p. 638,645

  摘要：

  DOI：

文献信息

• INSENSITIVE PLASTICIZER AND MELT-CASTABLE ENERGETIC MATERIAL
  申请人：THE UNITED STATES GOVERMENT AS REPRESENTED BY THE SECRETARY OF THE ARMY-U.S. ARMY RESEARCH LABORATOR

  公开号：US20190062287A1

  公开（公告）日：2019-02-28

  A method and compound includes mixing dichloroglyoxime with an alcohol containing an alkyne functional group in methanol to create a mixture; adding a salt compound and water to the mixture to create bis-isoxazole diol; and nitrating the bis-isoxazole diol to create 3,3′-bis-isoxazole-5,5′-bis-methylene dinitrate, which has the structural formula: The alcohol containing an alkyne functional group may include propargyl alcohol. The salt compound may include sodium bicarbonate. The method may include nitrating the bis-isoxazole diol with nitric acid. The nitric acid may include at least a concentration of 90% nitric acid in water. Alternatively, the method may include nitrating the bis-isoxazole diol with 100% nitric acid and acetic anhydride. The salt compound and the water may be added to the mixture over at least a six-hour period. The method may include mixing the mixture after adding the salt compound and the water for at least ten hours.

  一种方法和化合物包括将二氯基戊二酮与含有炔基官能团的醇在甲醇中混合以创建混合物；向混合物中添加盐化合物和水以创建双异噁唑二醇；然后对双异噁唑二醇进行硝化以创建3,3′-双异噁唑-5,5′-双亚甲基二硝酸酯，其结构式为：含有炔基官能团的醇可以包括丙炔醇。盐化合物可以包括碳酸氢钠。该方法可能包括使用硝酸对双异噁唑二醇进行硝化。硝酸可能包括至少90%浓度的硝酸溶解在水中。另外，该方法可能包括使用100%硝酸和乙酸酐对双异噁唑二醇进行硝化。盐化合物和水可能在至少六小时的时间内加入到混合物中。该方法可能在添加盐化合物和水后至少混合十小时。
• Insights into the reaction paths of copper(i) acetylides with dichloroglyoxime leading to 3,3′-biisoxazoles
  作者：M. A. Topchiy、G. K. Sterligov、A. A. Ageshina、S. A. Rzhevskiy、L. I. Minaeva、M. S. Nechaev、A. F. Asachenko

  DOI：10.1007/s11172-022-3437-y

  日期：2022.3

  Base-free reaction of dichloroglyoxime with copper(i) acetylides gave 3,3′-biisoxazoles via a nucleophilic substitution of the chlorine atom of dichloroglyoxime with the acetylene moiety followed by cyclization of the intermediate formed. The effects of the solvent on the product yields were studied. In the case of substituted copper acetylides, 5,5′-disubstituted 3,3′-biisoxazoles were obtained in the yields from moderate to high and high regioselectivity.

  二氯乙二肟与铜(i)乙酰化物发生无碱反应，通过二氯乙二肟的氯原子与乙炔基团发生亲核取代反应，然后形成的中间体发生环化反应，生成 3,3′-双异噁唑。研究了溶剂对产物产量的影响。在取代铜乙酰化物的情况下，得到了 5,5′-二取代的 3,3′-联异噁唑，产率从中等到高不等，并且具有很高的区域选择性。
• Insensitive plasticizer and melt-castable energetic material
  申请人：THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY OF THE ARMY-U.S. ARMY RESEARCH LABORATOR

  公开号：US10246428B2

  公开（公告）日：2019-04-02

  A method and compound includes mixing dichloroglyoxime with an alcohol containing an alkyne functional group in methanol to create a mixture; adding a salt compound and water to the mixture to create bis-isoxazole diol; and nitrating the bis-isoxazole diol to create 3,3′-bis-isoxazole-5,5′-bis-methylene dinitrate, which has the structural formula: The alcohol containing an alkyne functional group may include propargyl alcohol. The salt compound may include sodium bicarbonate. The method may include nitrating the bis-isoxazole diol with nitric acid. The nitric acid may include at least a concentration of 90% nitric acid in water. Alternatively, the method may include nitrating the bis-isoxazole diol with 100% nitric acid and acetic anhydride. The salt compound and the water may be added to the mixture over at least a six-hour period. The method may include mixing the mixture after adding the salt compound and the water for at least ten hours.

  一种方法和化合物包括将二氯乙二肟与含有炔官能团的醇在甲醇中混合，生成混合物；向混合物中加入盐化合物和水，生成双异噁唑二醇；将双异噁唑二醇硝化，生成结构式为 3,3′-双异噁唑-5,5′-双亚甲基二硝酸盐： 含有炔官能团的醇可以包括丙炔醇。盐化合物可包括碳酸氢钠。该方法可包括用硝酸硝化双异噁唑二醇。硝酸可包括浓度至少为 90% 的硝酸水溶液。或者，该方法可包括用 100% 硝酸和乙酸酐硝化双异噁唑二醇。盐化合物和水可在至少六小时内加入混合物中。该方法可包括在加入盐化合物和水后将混合物混合至少 10 小时。
• Quilico et al., Gazzetta Chimica Italiana, 1957, vol. 87, p. 638,646
  作者：Quilico et al.

  DOI：——

  日期：——
• Synthesis of bis-Isoxazole-bis-Methylene Dinitrate: A Potential Nitrate Plasticizer and Melt-Castable Energetic Material
  作者：Leah A. Wingard、Pablo E. Guzmán、Eric C. Johnson、Jesse J. Sabatini、Gregory W. Drake、Edward F. C. Byrd

  DOI：10.1002/cplu.201600470

  日期：2017.2

  The efficient and scalable synthesis of 3,3'-bis-isoxazole-5,5'-bis-methylene dinitrate and its energetic properties are described. The material has favorable sensitivity properties; energetic properties point toward its potential as both a melt-castable secondary explosive and as a propellant plasticizer.

  描述了3,3'-双-异恶唑-5,5'-双亚甲基二硝酸酯的有效和可扩展合成及其能量性质。该材料具有良好的敏感性。高能特性表明它既可以作为可熔铸的二次炸药，又可以作为推进剂增塑剂。