1-(4-methoxybenzyl)-3-methylthio-4-azetidin-2-one | 166324-16-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-methoxybenzyl)-3-methylthio-4-azetidin-2-one
• 英文别名: 4-[bis(phenylsulfanyl)methylidene]-1-[(4-methoxyphenyl)methyl]-3-methylsulfanylazetidin-2-one
• CAS: 166324-16-9
• 化学式: C₂₅H₂₃NO₂S₃
• 分子量: 465.661
• InChiKey: WVJGHJSMASECOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.52
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(4-methoxybenzyl)-3-methylthio-4-azetidin-2-one 在 N-氯代丁二酰亚胺 作用下， 以 四氯化碳 为溶剂， 反应 15.0h， 生成 4-(Bis-phenylsulfanyl-methylene)-3-chloro-1-(4-methoxy-benzyl)-3-methylsulfanyl-azetidin-2-one
  参考文献：
  名称：

  Uncatalyzed cationic olefin cyclizations of N-vinylic α-chloro-α-thioacetamides. Formation of β- and γ-lactams

  摘要：

  N-Vinylic alpha-chloro-alpha-thioacetamides were found to cyclize without a catalyst in two different manners depending upon the nature of the substituents at the terminus of the N-vinylic bond. Thus, bis(phenylthio)-substituted enamides 8a-c cyclized in a 4-exo-trig manner to give 4-methylene-beta-lactams 10a-c, whereas mono(phenylthio)-, monophenyl-, diphenyl-, and dialkyl-substituted congeners 23a,b, 28, and 38 cyclized in a 5-endo-trig manner to give gamma-lactams 26a,b, 30, and 39, respectively. The product 38 was transformed into an anticonvulsant agent ethosuximide (42).

  DOI：

  10.1016/0040-4020(95)00056-e
• 作为产物：
  描述：

  bis(phenylthio)acetaldehyde 在 N-氯代丁二酰亚胺 、 magnesium sulfate 、 N,N-二乙基苯胺 作用下， 以 四氯化碳 、 苯 为溶剂， 反应 41.5h， 生成 1-(4-methoxybenzyl)-3-methylthio-4-azetidin-2-one
  参考文献：
  名称：

  Uncatalyzed cationic olefin cyclizations of N-vinylic α-chloro-α-thioacetamides. Formation of β- and γ-lactams

  摘要：

  N-Vinylic alpha-chloro-alpha-thioacetamides were found to cyclize without a catalyst in two different manners depending upon the nature of the substituents at the terminus of the N-vinylic bond. Thus, bis(phenylthio)-substituted enamides 8a-c cyclized in a 4-exo-trig manner to give 4-methylene-beta-lactams 10a-c, whereas mono(phenylthio)-, monophenyl-, diphenyl-, and dialkyl-substituted congeners 23a,b, 28, and 38 cyclized in a 5-endo-trig manner to give gamma-lactams 26a,b, 30, and 39, respectively. The product 38 was transformed into an anticonvulsant agent ethosuximide (42).

  DOI：

  10.1016/0040-4020(95)00056-e