(3-溴异恶唑-4-基)甲醇 | 111303-37-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: (3-溴异恶唑-4-基)甲醇
• 英文名称: (3-Bromo-isoxazol-4-yl)-methanol
• 英文别名: 3-Bromo-4-isoxazolemethanol；(3-bromo-1,2-oxazol-4-yl)methanol
• CAS: 111303-37-8
• 化学式: C₄H₄BrNO₂
• 分子量: 177.985
• InChiKey: DWWKSWUMQHEBMZ-UHFFFAOYSA-N

物化性质

• 沸点：
  308.1±27.0 °C(Predicted)
• 密度：
  1.864±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dihydroartemisinin 、 (3-溴异恶唑-4-基)甲醇 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 0.25h， 以63%的产率得到3-bromo-4-[[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxymethyl]-1,2-oxazole
  参考文献：
  名称：

  Antimalarial activity of new ethers and thioethers of dihydroartemisinin

  摘要：

  Various ethers and thioethers of dihydroartemisinin were prepared by treating dihydroartemisinin with hydroxy alkyl, substituted phenol, hydroxy aralkyl, hydroxy alkynyl and hydroxy heteroalkyl or thiols in the presence of BF(3)Et(2)O. The thioethers 64 and 65 were further oxidised to the respective sulfoxides. These derivatives were tested in the Plasmodium berghei K-173-infected mice and some active compounds were tested in chloroquine-resistant P yoelii nigeriensis (NS)-infected mice. Initially the compounds were administered subcutaneously and subsequently by the oral route. The antimalarial activity of the compounds 22, 23, 36, 66 and 79 were found to be comparable to that of arteether when tested in the K-173-infected mice. These compounds also showed activity in the P y nigeriensis (NS)-infected mice.

  DOI：

  10.1016/0223-5234(96)88287-0
• 作为产物：
  描述：

  1,1-二溴甲醛肟 、 2-丙炔-1-醇 生成 (3-溴异恶唑-4-基)甲醇
  参考文献：
  名称：

  CHIARINO D.; NAPOLETANO M.; SALA A., J. HETEROCYCL. CHEM., 24,(1987) N 1, 45-46

  摘要：

  DOI：

文献信息

• 1,3-Dipolar cycloaddition synthesis of 3-bromo-5-substituted isoxazoles, useful intermediates for the preparation of pharmacologically active compounds
  作者：D. Chiarino、M. Napoletano、A. Sala

  DOI：10.1002/jhet.5570240109

  日期：1987.1

  monosubstituted acetylenic derivatives 4 to give 3-bromo-5-substituted isoxazoles 5 in high yield. The experimental conditions necessary to overcome difficulties such as the low reactivity of acetylenic dipolarophiles and the high tendency to dimerization of bromonitrile oxide 2, are discussed; the regioselectivity of this 1,3-dipolar cycloaddition is also studied. The obtained improvements in the synthesis of

  Bromonitrile氧化物2，从容易获得的二溴甲醛肟生成1，与单取代的炔属衍生物进行反应4，得到3-溴-5-异恶唑取代的5以高收率。讨论了克服困难的条件，例如乙炔双极性亲和剂的低反应性和溴代腈氧化物2的二聚化趋势高。还研究了这种1，3-偶极环加成反应的区域选择性。据报道在某些药理活性化合物的合成中获得的改进。
• Bromonitrile oxide [3+2] cycloadditions in water
  作者：John C. Rohloff、James Robinson、John O. Gardner

  DOI：10.1016/s0040-4039(00)79827-3

  日期：1992.5

  Bromonitrite oxide can be generated homogeneously in water at acidic pH, allowing efficient [3 + 2] cycloaddition with water soluble olefins and acetylenes. Allylammonium salts react with high regioselectivity and without the need for N-group protection.