7-chloro-3-(1-hydroxy-2,2-dimethyl-but-3-enyl)-1H-quinoline-2-thione | 1620211-72-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 7-chloro-3-(1-hydroxy-2,2-dimethyl-but-3-enyl)-1H-quinoline-2-thione
• CAS: 1620211-72-4
• 化学式: C₁₅H₁₆ClNOS
• 分子量: 293.817
• InChiKey: PWIBIXWTXZEXCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  36.02
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  7-chloro-3-(1-hydroxy-2,2-dimethyl-but-3-enyl)-1H-quinoline-2-thione 在 碘 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以80%的产率得到6-chloro-2,2a,10-trihydro-11,11-dimethylfuro[2',4':4,6]thiopyrano[2,3-b]quinoline
  参考文献：
  名称：

  I2-catalyzed base-free cyclization of 3-homoallylquinoline-2-thiones: facile synthesis of tetracyclic, furothiopyrano[2,3-b]quinolines

  摘要：

  I-2-catalyzed base-free reactions of 3-homoallylquinoline-2-thiones have been described for the synthesis of tetracyclic quinolines, tetrahydrofuro [2',4':4,6]thiopyrano[2,3-Nquinolines in excellent yields. Similarly, I2-catalyzed reactions could proceed to tricyclic quinolines from hydroxyl group protected 3-homoallylquinoline-2-thiones. However, deprotection of group in tricyclic quinoline with HI again transformed into tetracyclic quinoline. The sulfonium salt intermediate has been proposed to explain these reactions. (C) Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.041
• 作为产物：
  描述：

  2,7-二氯喹啉-3-羧醛 在 sodium sulfide 、 indium 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 7-chloro-3-(1-hydroxy-2,2-dimethyl-but-3-enyl)-1H-quinoline-2-thione
  参考文献：
  名称：

  I2-catalyzed base-free cyclization of 3-homoallylquinoline-2-thiones: facile synthesis of tetracyclic, furothiopyrano[2,3-b]quinolines

  摘要：

  I-2-catalyzed base-free reactions of 3-homoallylquinoline-2-thiones have been described for the synthesis of tetracyclic quinolines, tetrahydrofuro [2',4':4,6]thiopyrano[2,3-Nquinolines in excellent yields. Similarly, I2-catalyzed reactions could proceed to tricyclic quinolines from hydroxyl group protected 3-homoallylquinoline-2-thiones. However, deprotection of group in tricyclic quinoline with HI again transformed into tetracyclic quinoline. The sulfonium salt intermediate has been proposed to explain these reactions. (C) Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.041