N,2-dimethyl-N-<1-(methylthio)ethenyl>-2-propenamide | 136788-04-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代羰基化合物
• 英文名称: N,2-dimethyl-N-<1-(methylthio)ethenyl>-2-propenamide
• 英文别名: N,2-dimethyl-N-(1-methylsulfanylethenyl)prop-2-enamide
• CAS: 136788-04-0
• 化学式: C₈H₁₃NOS
• 分子量: 171.263
• InChiKey: WOQDXGGENWMCRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  11.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N,2-dimethyl-N-<1-(methylthio)ethenyl>-2-propenamide 在 sodium tetrahydroborate 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲醇 、 乙腈 、 苯 为溶剂， 反应 12.5h， 生成 1,3-二甲基-哌啶-2-酮
  参考文献：
  名称：

  Photocyclization of Enamides. 38. Reductive Photocyclization of a-(Methylthio)- and a-(Arylthio)enamides

  摘要：

  Reductive photocyclization of alpha-(methylthio)enamide (2) gave exclusively six-membered lactams (3) and (4) while the same reaction of alpha-(arylthio)enamides (6) and (12) was found to afford-five-membered lactams (7) and (13) as major products. A novel total synthesis of (+/-)-polyzonimine (18b) was accomplished by applying the newly found reductive photocyclization of alpha-(naphthylthio)enamide leading to the formation of five-membered lactams.

  DOI：

  10.3987/com-93-6465
• 作为产物：
  描述：

  methyl N-methylthioacetimidate 、 甲基丙烯酰氯 在 三乙胺 作用下， 以 苯 为溶剂， 反应 3.5h， 以99%的产率得到N,2-dimethyl-N-<1-(methylthio)ethenyl>-2-propenamide
  参考文献：
  名称：

  Photocyclization of Enamides. 38. Reductive Photocyclization of a-(Methylthio)- and a-(Arylthio)enamides

  摘要：

  Reductive photocyclization of alpha-(methylthio)enamide (2) gave exclusively six-membered lactams (3) and (4) while the same reaction of alpha-(arylthio)enamides (6) and (12) was found to afford-five-membered lactams (7) and (13) as major products. A novel total synthesis of (+/-)-polyzonimine (18b) was accomplished by applying the newly found reductive photocyclization of alpha-(naphthylthio)enamide leading to the formation of five-membered lactams.

  DOI：

  10.3987/com-93-6465

文献信息

• Reductive Photocyclization of a-Methylthio- and a-Arylthioenamides
  作者：Takeaki Naito、Hiromi Tanada、Toshiko Kiguchi、Ichiya Ninomiya

  DOI：10.3987/com-91-5766

  日期：——

  Reductive photocyclization of alpha -methylthio- and alpha -arylthioenamides (2a-c) gave six-membered lactams (3a-d) and five-membered lactams (4a,b).