5-甲基-4-硝基异噁唑 | 1122-06-1

• 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-甲基-4-硝基异噁唑
• 英文名称: 4-nitro-5-methylisoxazole
• 英文别名: 5-methyl-4-nitroisoxazole；5-methyl-4-nitro-isoxazole；5-Methyl-4-nitro-isoxazol；4-Nitro-5-methyl-isoxazole；5-Methyl-4-nitroisoxazol；5-methyl-4-nitro-1,2-oxazole
• CAS: 1122-06-1
• 化学式: C₄H₄N₂O₃
• mdl: MFCD06638028
• 分子量: 128.087
• InChiKey: NYVORXIBNGBOCV-UHFFFAOYSA-N

物化性质

• 沸点：
  40 °C(Press: 0.4 Torr)
• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-甲基-4-硝基异噁唑 在 ammonium chloride 、 锌 作用下， 以 水 为溶剂， 以82%的产率得到5-甲基-4-异噁唑胺
  参考文献：
  名称：

  赫斯特朗·冯取代2-氨基恶唑4-碳三腈†

  摘要：

  取代的2-氨基恶唑-4-腈的制备

  DOI：

  10.1002/hlca.19890720317
• 作为产物：
  描述：

  5-甲基异恶唑 在 硝酸铵 作用下， 以 三氟乙酸 为溶剂， 以67%的产率得到5-甲基-4-硝基异噁唑
  参考文献：
  名称：

  赫斯特朗·冯取代2-氨基恶唑4-碳三腈†

  摘要：

  取代的2-氨基恶唑-4-腈的制备

  DOI：

  10.1002/hlca.19890720317

文献信息

• Repair of sulfur mustard-induced DNA damage in mammalian cells measured by a host cell reactivation assay
  作者：Z. Matijasevic、M.L. Precopio、J.E. Snyder、D.B. Ludlum

  DOI：10.1093/carcin/22.4.661

  日期：2001.4

  DNA damage is thought to be the initial event that causes sulfur mustard (SM) toxicity, while the ability of cells to repair this damage is thought to provide a degree of natural protection. To investigate the repair process, we have damaged plasmids containing the firefly luciferase gene with either SM or its monofunctional analog, 2-chloroethyl ethyl sulfide (CEES). Damaged plasmids were transfected into wild-type and nucleotide excision repair (NER) deficient Chinese hamster ovary cells; these cells were also transfected with a second reporter plasmid containing Renilla luciferase as an internal control on the efficiency of transfection. Transfected cells were incubated at 37°C for 27 h and then both firefly and Renilla luciferase intensities were measured on the same samples with the dual luciferase reporter assay. Bioluminescence in lysates from cells transfected with damaged plasmid, expressed as a percentage of the bioluminescence from cells transfected with undamaged plasmid, is increased by host cell repair activity. The results show that NER-competent cells have a higher reactivation capacity than NER-deficient cells for plasmids damaged by either SM or CEES. Significantly, NER-competent cells are also more resistant to the toxic effects of SM and CEES, indicating that NER is not only proficient in repairing DNA damage caused by either agent but also in decreasing their toxicity. This host cell repair assay can now be used to determine what other cellular mechanisms protect cells from mustard toxicity and under what conditions these mechanisms are most effective.

  DNA损伤被认为是引起硫芥(SM)毒性的起始事件，而细胞修复这种损伤的能力则被认为提供了一定程度的自然保护。为了研究修复过程，我们使用SM或其单功能类似物2-氯乙基乙基硫化物(CEES)对含有萤火虫荧光素酶基因的质粒进行了损伤。损伤后的质粒被转染到野生型和核苷酸切除修复(NER)缺陷的中国仓鼠卵巢细胞中；这些细胞还转染了第二个报告质粒，其中包含海肾荧光素酶作为转染效率的内部对照。转染后的细胞在37°C下孵育27小时，然后用双荧光素酶报告分析法在同一样本上测量萤火虫和海肾荧光素酶的强度。细胞裂解液中转染了损伤质粒的生物发光，以转染了未损伤质粒的细胞的生物发光的百分比表示，随宿主细胞修复活性而增加。结果显示，对于被SM或CEES损伤的质粒，具有NER能力的细胞比NER缺陷的细胞具有更高的再激活容量。值得注意的是，具有NER能力的细胞对SM和CEES的毒性影响也更具抵抗力，表明NER不仅擅长修复这两种试剂引起的DNA损伤，还能降低它们的毒性。现在，这种宿主细胞修复分析可以用来确定其他哪些细胞机制保护细胞免受芥子气毒性影响及其在这些机制最有效时的条件。
• Base-induced ring cleavage of 4-functionalized-3-unsubstituted isoxazoles. Synthesis of 5-aminoazoles and 4-cyanoazoles
  作者：A. Alberola、L. F. Antolin、A. M. Gonzalez、M. A. Laguna、F. J. Pulido

  DOI：10.1002/jhet.5570230414

  日期：1986.7

  The base-induced ring cleavage of 4-nitro-(Ia), 4-ethoxycarbonyl- (Ib) and 4-acetyl-5-methylisoxazole (Ic) and the conversion of the resulting β-cyanoenolates and β-enaminonitriles into 5-aminoazoles and 4-cyanoazoles was studied.

  4-硝基-（Ia），4-乙氧基羰基-（Ib）和4-乙酰基-5-甲基异恶唑（Ic）的碱诱导的环裂解以及所得的β-氰基烯酸酯和β-烯腈转化为5-氨基唑并研究了4-氰基唑。
• Synthesis of Dinitro-Substituted Furans, Thiophenes, and Azoles
  作者：Alan Katritzky、Anatoliy Vakulenko、Jothilingam Sivapackiam、Bogdan Draghici、Reddy Damavarapu

  DOI：10.1055/s-2008-1032187

  日期：2008.3

  nitration of the corresponding mononitro furans with fuming nitric acid, thiophenes with acetyl nitrate, and thiazoles with trifluoroacetyl nitrate, gave dinitro-substituted furans, thiophenes, and thiazoles. The nitrations of 2-alkylthiophenes with 3 and 5 molar equivalents of acetyl nitrate, generated in situ, are discussed. Reactions of the mononitro furans with fuming nitric acid gave 1,1,5,5-tetrasubstituted

  相应的单硝基呋喃用发烟硝酸直接硝化，噻吩用乙酰硝酸酯直接硝化，噻唑用三氟乙酰硝酸酯直接硝化，得到二硝基取代的呋喃、噻吩和噻唑。讨论了原位生成的 2-烷基噻吩与 3 和 5 摩尔当量的乙酰硝酸酯的硝化反应。单硝基呋喃与发烟硝酸反应生成 1,1,5,5-四取代二氢呋喃作为副产物。用肼或其甲基或苯基衍生物处理 5-甲基-4-硝基异恶唑，然后用过氧化氢 (50%) 氧化相应的 4-氨基-5-硝基-1H-吡唑，得到 4,5-二硝基 -1H -吡唑。1-烷基-3,5-二硝基-1H-[1,2,4]三唑的安全一锅法合成是由双氰胺开发的。
• The Reactions of 3-Unsubstituted Isoxazolium Salts with 1,2-Dinucleophiles. Synthesis of 4-Functionalized 3-Aminoisoxazoles and 3-Aminopyrazoles
  作者：A. Alberola、L. F. Antolín、P. Cuadrado、A. M. González、M. A. Laguna、F. J. Pulido

  DOI：10.1055/s-1988-27512

  日期：——

  The reaction of 3-unsubstituted isoxazolium salts with 1,2-dinucleophiles (hydroxylamine, hydrazine, methylhydrazine, phenylhydrazine, 4-nitrophenylhydrazine, semicarbazide) in boiling ethanol, affords 4-functionalized 3-alkylaminoisoxazoles and 3-alkylaminopyrazoles in high yields. The procedure is quite general, thus providing a new method for the synthesis of 3-aminoazoles with potential biological activity. Mechanistic pathways for these transformations are proposed.

  未取代的3-异氧杂盐与1,2-双亲核试剂（羟胺、肼、消旋肼、苯肼、4-硝基苯肼、半脲）在沸腾的乙醇中反应，能够高产率地生成4-功能化的3-烷基氨基异氧杂烯和3-烷基氨基吡唑。这一方法相当通用，因此为合成具有潜在生物活性的3-氨基杂环化合物提供了一种新方法。对这些转化的机制路径也进行了提出。
• Synthesis of 4(5)-acyl-, 1-substituted 5-acyl- and 1-substituted 4-acyl-1H-imidazoles from 4-aminoisoxazoles
  作者：Lawrence A. Reiter

  DOI：10.1021/jo00389a015

  日期：1987.6