raphanusamide | 148520-23-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫代内酰胺类
• 英文名称: raphanusamide
• 英文别名: (3E)-3-(methoxymethylidene)pyrrolidine-2-thione
• CAS: 148520-23-4
• 化学式: C₆H₉NOS
• 分子量: 143.21
• InChiKey: FXKRKZYGKOWUNE-SNAWJCMRSA-N

物化性质

• 沸点：
  210.8±50.0 °C(predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  raphanusamide 以 甲醇 、 水 为溶剂， 反应 6.25h， 生成 cis-3-(methylthio) methylene-2-pyrrolidinethione
  参考文献：
  名称：

  Structure-activity relationships of raphanusanins and their analogues

  摘要：

  The structure-activity relationship of raphanusanins A and B {(3R*,6R*)-and (3R*,6S*)-3-[methoxy(methylthio)methyl]-2-pyrrolidinethione, respectively} and their analogues has been studied for the inhibition of the growth of lettuce hypocotyls and Amaranthus roots. Pyrrolidinethione compounds showed higher activity than pyrrolidinones. The presence of a methoxy(methylthio)methyl group or of a methylthiomethylene moiety at C-3 of pyrrolidinethione was a dominant factor for higher activity. The bis(methylthio)methyl derivative also gave a similar inhibitory activity. It was established that the active sites in the chemical structure of the raphanusanins and their analogues were the thioamide moiety at C-2 of the skeleton and a methoxy(methylthio)methyl, bis(methylthio)methyl, or methylthiomethylene group in the C-3 position of the side chain.

  DOI：

  10.1016/0031-9422(93)85140-m

文献信息

• Structure-activity relationships of raphanusanins and their analogues
  作者：Masako Sakoda、Kenji Usui、Kozo Ishizuka、Nobuyuki Harada、Hiroshi Ono、Hisashi Uda、Koji Hasegawa

  DOI：10.1016/0031-9422(93)85140-m

  日期：——

  The structure-activity relationship of raphanusanins A and B (3R*,6R*)-and (3R*,6S*)-3-[methoxy(methylthio)methyl]-2-pyrrolidinethione, respectively} and their analogues has been studied for the inhibition of the growth of lettuce hypocotyls and Amaranthus roots. Pyrrolidinethione compounds showed higher activity than pyrrolidinones. The presence of a methoxy(methylthio)methyl group or of a methylthiomethylene moiety at C-3 of pyrrolidinethione was a dominant factor for higher activity. The bis(methylthio)methyl derivative also gave a similar inhibitory activity. It was established that the active sites in the chemical structure of the raphanusanins and their analogues were the thioamide moiety at C-2 of the skeleton and a methoxy(methylthio)methyl, bis(methylthio)methyl, or methylthiomethylene group in the C-3 position of the side chain.