5-硝基-1,2-恶唑-3-羧酸乙酯 | 155088-43-0

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 5-硝基-1,2-恶唑-3-羧酸乙酯
• 英文名称: ethyl 5-nitroisoxazole-3-carboxylate
• 英文别名: ethyl 5-nitro-1,2-oxazole-3-carboxylate
• CAS: 155088-43-0
• 化学式: C₆H₆N₂O₅
• 分子量: 186.124
• InChiKey: IRBHGCRWZVUNHP-UHFFFAOYSA-N

物化性质

• 沸点：
  326.5±22.0 °C(Predicted)
• 密度：
  1.413±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2934999090

反应信息

• 作为产物：
  描述：

  5-Nitro-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 以31%的产率得到5-硝基-1,2-恶唑-3-羧酸乙酯
  参考文献：
  名称：

  Nitroisoxazoles by Manganese(IV) Oxide Oxidation of Nitro-4,5-dihydroisoxazoles

  摘要：

  以氧化锰（IV）为氧化剂，从适当的 3-和 5-硝基-4,5-二氢异噁唑制备了芳基和烷基取代的 3-和 5-硝基异噁唑衍生物。一些 3-硝基-4-取代的异噁唑是通过 2-取代的 3-溴-l-卤丙烷与亚硝酸钠反应直接制备的。

  DOI：

  10.1055/s-1993-26010

文献信息

• Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 5-Nitroisoxazoles
  作者：Yulia A. Volkova、Elena B. Averina、Dmitry A. Vasilenko、Kseniya N. Sedenkova、Yuri K. Grishin、Per Bruheim、Tamara S. Kuznetsova、Nikolai S. Zefirov

  DOI：10.1021/acs.joc.8b03086

  日期：2019.3.15

  A novel reaction of tetranitromethane with electrophilic alkenes in the presence of triethylamine affording substituted 5-nitroisoxazoles is described. Triethylamine reacts with tetranitromethane to generate N-nitrotriethylammonium and trinitromethanide. This process provides the heterocyclization of electrophilic alkenes. A variety of α,β-unsaturated aldehydes, ketones, esters, amides, phosphonates

  描述了在三乙胺存在下四硝基甲烷与亲电烯烃的新型反应，提供了取代的5-硝基异恶唑。三乙胺与四硝基甲烷反应生成N-硝基三乙铵和三硝基甲烷。该过程提供了亲电烯烃的杂环化。各种α，β-不饱和醛，酮，酯，酰胺，膦酸酯，硝基和硫化合物参与了杂环化反应，并以良好或高收率获得了多种官能化的5-硝基异恶唑。讨论了反应的范围和局限性以及机理建议。
• Heterocyclic amides with anti-tuberculosis activity
  申请人：Lee E. Richard

  公开号：US20050222408A1

  公开（公告）日：2005-10-06

  Compounds having the general structure: wherein A is selected from the group consisting of oxygen, sulfur, and NR 15 , and R 15 is selected from the group consisting of H, alkyl, aryl, substituted alkyl, and substituted aryl; B,D, and E are each independently selected from the group consisting of CH, nitrogen, sulfur and oxygen; R 1 is selected from the group consisting of nitro, halo, alkyl ester, arylsulfanyl, arylsulfinyl, arylsulfonyl and sulfonic acid; t is an integer from 1 to 3; and X is a substituted amide, and methods of using the novel compounds for treating infections caused by microorganisms, including Mycobacterium tuberculosis.

  具有一般结构的化合物：其中A从氧、硫和NR15组成的群体中选择，R15从H、烷基、芳基、取代烷基和取代芳基组成的群体中选择；B、D和E分别独立地从CH、氮、硫和氧组成的群体中选择；R1从硝基、卤素、烷基酯、芳基硫醚、芳基亚砜、芳基砜基和磺酸中选择；t为1到3的整数；X为取代酰胺，并且使用这些新化合物治疗由微生物引起的感染的方法，包括结核分枝杆菌。
• [EN] HETEROCYCLIC AMIDES WITH ANTI-TUBERCULOSIS ACTIVITY<br/>[FR] AMIDES HETEROCYCLIQUES A ACTIVITE ANTI-TUBERCULINIQUE
  申请人：UNIV TENNESSEE RES FOUNDATION

  公开号：WO2005007625A2

  公开（公告）日：2005-01-27

  Compounds having the general structure (I) : wherein A is selected from the group consisting of oxygen, sulfur, and NR15, and R15 is selected from the group consisting of H, alkyl, aryl, substituted alkyl, and substituted aryl; B, D, and E are each independently selected from the group consisting of CH, nitrogen, sulfur and oxygen; R1 is selected from the group consisting of nitro, halo, alkyl ester, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl and sulfonic acid; t is an integer from 1 to 3; and X is a substituted amide and methods of using the novel compounds for treating infections caused microorganisms, including Mycobacterium tuberculosis.
• Nitroisoxazoles by Manganese(IV) Oxide Oxidation of Nitro-4,5-dihydroisoxazoles
  作者：Giuseppe Diamantini、Ermanno Duranti、Andrea Tontini

  DOI：10.1055/s-1993-26010

  日期：——

  Aryl and alkyl substituted 3- and 5-nitroisoxazole derivatives were prepared from the appropriate 3- and 5-nitro-4,5-dihydroisoxazoles using manganese(IV) oxide as oxidizing agent. Some of the 3-nitro-4-substituted isoxazoles were prepared directly by reaction of 2-substituted 3-bromo-l-halopropanes with sodium nitrite.

  以氧化锰（IV）为氧化剂，从适当的 3-和 5-硝基-4,5-二氢异噁唑制备了芳基和烷基取代的 3-和 5-硝基异噁唑衍生物。一些 3-硝基-4-取代的异噁唑是通过 2-取代的 3-溴-l-卤丙烷与亚硝酸钠反应直接制备的。