allyl N-hydroxybenzimidothioate | 1568950-25-3

• 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: allyl N-hydroxybenzimidothioate
• CAS: 1568950-25-3
• 化学式: C₁₀H₁₁NOS
• 分子量: 193.269
• InChiKey: CMWAVFXIAGJZEQ-UHFFFAOYSA-N

物化性质

• 沸点：
  320.6±35.0 °C(predicted)
• 密度：
  1.06±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  32.59
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  allyl N-hydroxybenzimidothioate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以16%的产率得到3-phenyl-5-vinyl-1,4,2-oxathiazole
  参考文献：
  名称：

  Synthesis of 1,4,2-Oxathiazoles via Oxidative Cyclization of Thiohydroximic Acids

  摘要：

  An oxidative formation of 1,4,2-oxathiazoles from readily available thiohydroximic acids is reported. A variety of alkyl, aryl, and heteroaryl substituents are well tolerated for both the thiohydroximic acid and activating fragments, and the reaction has been demonstrated on gram-scale. This reaction represents the only method currently available to prepare a diverse set of oxathiazoles and expands the chemistry of C-H oxidation via appended N-OH functional groups. Finally, we also demonstrate the rapid preparation of a 1,4,2-oxathiazole analog of an anticancer lead molecule.

  DOI：

  10.1021/acs.orglett.5b02256
• 作为产物：
  描述：

  苯甲醛肟 在 sodium sulfide 、 N-氯代丁二酰亚胺 、 四丁基碘化铵 、 三乙胺 作用下， 以 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 allyl N-hydroxybenzimidothioate
  参考文献：
  名称：

  Synthesis of Thiohydroxamic Acids and Thiohydroximic Acid Derivatives

  摘要：

  An improved and expanded preparation of thiohydroxamic acids is reported along with a one-pot conversion of these compounds to novel thiohydroximic acid derivatives. A variety of aryl, heteroaryl, and alkyl substituents are well tolerated to provide a rapid approach to alkene-functionalized thiohydroximic acids that serve as potentially useful building blocks for organic synthesis.

  DOI：

  10.1021/jo500080x