5-(2,5-dimethoxyphenyl)-1,3,4-oxathiazol-2-one | 1424328-51-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(2,5-dimethoxyphenyl)-1,3,4-oxathiazol-2-one
• 英文别名: 5-(2,5-Dimethoxyphenyl)-1,3,4-oxathiazol-2-one
• CAS: 1424328-51-7
• 化学式: C₁₀H₉NO₄S
• 分子量: 239.252
• InChiKey: XXAHIACZGSIKAP-UHFFFAOYSA-N

物化性质

• 沸点：
  375.1±52.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  82.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(2,5-dimethoxyphenyl)-1,3,4-oxathiazol-2-one 在 ammonium cerium (IV) nitrate 、 copper diacetate 、 potassium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 邻二氯苯 、 乙腈 为溶剂， 反应 24.0h， 生成 2,5-di(aziridin-1-yl)-3-(5-(3-bromo-1H-pyrazol-1-yl)-1,2,4-thiadiazol-3-yl)cyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  关键步骤通过腈腈环加成反应设计和合成二叠氮基醌醌噻二唑杂化物

  摘要：

  从2-羟基-5-甲氧基苯甲酸1开始，以7步合成顺序合成了一系列新型的二叠氮基醌醌噻二唑杂化物（9a – 9j）。该方案的关键步骤涉及恶唑烷酮4与对甲苯磺酰基氰的腈类硫化物环加成反应，以获得1,2,4-噻二唑衍生物5。我们已经证明噻二唑5的对甲苯磺酰基可以被各种氮杂环置换以产生未知的3，5-二取代的噻二唑衍生物。

  DOI：

  10.1016/j.tetlet.2016.02.082
• 作为产物：
  描述：

  2,5-二甲氧基苯甲酸 在 ammonium hydroxide 、 氯化亚砜 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 26.0h， 生成 5-(2,5-dimethoxyphenyl)-1,3,4-oxathiazol-2-one
  参考文献：
  名称：

  3H-1,2,4-Dithiazol-3-one compounds as novel potential affordable antitubercular agents

  摘要：

  Small molecules with oxathiazol-2-one moiety were recently reported as potent inhibitors of Mycobacterium bovis var. bacilli Calmette-Guerin (BCG), among which HT1171 was the most potent and selective proteasome inhibitor. Herein we synthesized a series of novel compounds by bioisosteric replacement of the oxathiazol-2-one ring with 3H-1,2,4-dithiazol-3-one, and also fifteen 1,3,4-oxathiazol-2-one molecules in order for potency comparison and structure-activity relationship elucidation since their antibacterial effects on the virulent strains were not evaluated before. All the compounds were assessed for antitubercular activities on the virulent H37Rv strain by a serial dilution method. Among the tested compounds, 3H-1,2,4-dithiazol-3-one compound 4n was found to be the most active with a lowest MIC90 value of 1 mu g/mL. Furthermore, the cytotoxicities of all the compounds against normal human liver cell line L02 were determined by an MTT method. Compound 4n displayed a lower inhibitory ratio than HT1171 at the concentration of 100 mu M, indicating its better safety profile. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.065

文献信息

• Synthesis of spiroindene-1,3-dione isothiazolines via a cascade michael/1,3-dipolar cycloaddition reaction of 1,3,4-oxathiazol-2-one and 2-arylidene-1,3-indandiones
  作者：Anjaiah Aitha、Satyanarayana Yennam、Manoranjan Behera、Jaya Shree Anireddy

  DOI：10.1016/j.tetlet.2016.12.089

  日期：2017.2

  The reaction of 1,3,4-oxathiazol-2-one derivative with 2-arylidene-1,3-indandione to furnish novel spiroindene-1,3-dione isothiazoline derivatives by Michael/1,3-dipolar [3+2]-cycloaddition reaction was investigated. The key 1,3-dipolar cycloaddition reaction step was examined in toluene solvent at reflux temperature to obtain mixture of two regioisomers (6a and 6b - 14a and 14b) and single isomers (15-20). The scope of this new reaction was demonstrated with many examples with high reactivity and yields. (C) 2017 Elsevier Ltd. All rights reserved.