3-methylbut-2-en-1-yl N-((perfluorobenzoyl)oxy)cyclopropanecarbimidothioate | 1568951-16-5

• 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: 3-methylbut-2-en-1-yl N-((perfluorobenzoyl)oxy)cyclopropanecarbimidothioate
• CAS: 1568951-16-5
• 化学式: C₁₆H₁₄F₅NO₂S
• 分子量: 379.351
• InChiKey: UEXMOJQQPCTBHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-methylbut-2-en-1-yl N-((perfluorobenzoyl)oxy)cyclopropanecarbimidothioate 在 copper(I) bromide dimethylsulfide complex 、 lithium bromide 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.5h， 以52%的产率得到4-(2-bromopropan-2-yl)-2-cyclopropyl-4,5-dihydrothiazole
  参考文献：
  名称：

  Synthesis of Thiazolines by Copper Catalyzed Aminobromination of Thiohydroximic Acids

  摘要：

  A copper catalyzed aminobromination of Alkene tethered thiohydroximic acids is described, providing a rapid approach to unnatural thiazoline scaffolds not readily available via existing methods. Moderate to high yields of bromothiazolines are obtained with alkyl- and aryl-substituted thiohydroximic acid building blocks containing mono-, di-, and trisubstituted alkenes. The reaction provides high levels of 5-exo selectivity, and terminally monosubstituted alkenes result in predominant syn-diastereoselectivity.

  DOI：

  10.1021/ol500588v
• 作为产物：
  描述：

  五氟苯甲酰氯 、 N-hydroxycyclopropanecarbothioamide 、 1-溴-3-甲基-2-丁烯 在 四丁基碘化铵 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以26%的产率得到3-methylbut-2-en-1-yl N-((perfluorobenzoyl)oxy)cyclopropanecarbimidothioate
  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