3,3-dichloro-1-isopropyl-4-(4-methoxyphenyl)-2-azetidinone | 418765-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 3,3-dichloro-1-isopropyl-4-(4-methoxyphenyl)-2-azetidinone
• 英文别名: 4-(4-Methoxyphenyl)-1-isopropyl-3,3-dichloroazetidine-2-one；3,3-dichloro-4-(4-methoxyphenyl)-1-propan-2-ylazetidin-2-one
• CAS: 418765-66-9
• 化学式: C₁₃H₁₅Cl₂NO₂
• 分子量: 288.174
• InChiKey: SFNZVIHZYLBKRX-UHFFFAOYSA-N

物化性质

• 熔点：
  106.7-107.4 °C
• 沸点：
  415.3±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3-dichloro-1-isopropyl-4-(4-methoxyphenyl)-2-azetidinone 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以90%的产率得到3,3-dichloro-1-isopropyl-2-(4-methoxyphenyl)azetidine
  参考文献：
  名称：

  Rearrangement of 2-Aryl-3,3-dichloroazetidines:  Intermediacy of 2-Azetines

  摘要：

  An easy synthesis of 2-aryl-3,3-dichloroazetidines, a rather unexplored class of azaheterocycles, is described. The title compounds were easily obtained by reduction of the corresponding 4-aryl-3,3dichloro-2-azetidinones with monochloroalane, which in turn were synthesized by a ketene-imine [2 + 2] cycloaddition. The reactivity of 3,3-dichloroazetidines with bases was investigated, yielding 2-[dimethoxy(aryl)methyl]aziridines by ring contraction when treated with sodium methoxide. Furthermore, reacting the 3,3-dichloroazetidines with sodium hydride in DMSO, followed by aqueous workup, afforded 1-alkyl-2-aroylaziridines, by hydrolysis of the intermediate 2-azetines and ring closure of the transient 3-amino-2-chloro-1-phenyl-1-propanone derivatives. Monitoring this reaction in an NMR tube, using sodium hydride in DMSO-d(6),, allowed the characterization of the intermediate strained heterocyclic enamines, i.e., 2-azetines, by H-1 and C-13 NMR.

  DOI：

  10.1021/jo010914j
• 作为产物：
  描述：

  二氯乙酰氯 、 2,3,6,7-tetrahydro-3-isopropyl-2-(4-methoxylphenyl)-cyclopenta[e][1,3]oxazin-4(5H)-one 在 三乙胺 作用下， 以 苯 为溶剂， 反应 1.0h， 以77%的产率得到3,3-dichloro-1-isopropyl-4-(4-methoxyphenyl)-2-azetidinone
  参考文献：
  名称：

  Rearrangement of 2-Aryl-3,3-dichloroazetidines:  Intermediacy of 2-Azetines

  摘要：

  An easy synthesis of 2-aryl-3,3-dichloroazetidines, a rather unexplored class of azaheterocycles, is described. The title compounds were easily obtained by reduction of the corresponding 4-aryl-3,3dichloro-2-azetidinones with monochloroalane, which in turn were synthesized by a ketene-imine [2 + 2] cycloaddition. The reactivity of 3,3-dichloroazetidines with bases was investigated, yielding 2-[dimethoxy(aryl)methyl]aziridines by ring contraction when treated with sodium methoxide. Furthermore, reacting the 3,3-dichloroazetidines with sodium hydride in DMSO, followed by aqueous workup, afforded 1-alkyl-2-aroylaziridines, by hydrolysis of the intermediate 2-azetines and ring closure of the transient 3-amino-2-chloro-1-phenyl-1-propanone derivatives. Monitoring this reaction in an NMR tube, using sodium hydride in DMSO-d(6),, allowed the characterization of the intermediate strained heterocyclic enamines, i.e., 2-azetines, by H-1 and C-13 NMR.

  DOI：

  10.1021/jo010914j

文献信息

• Rearrangement of 2-Aryl-3,3-dichloroazetidines:  Intermediacy of 2-Azetines
  作者：Yves Dejaegher、Sven Mangelinckx、Norbert De Kimpe

  DOI：10.1021/jo010914j

  日期：2002.4.1

  An easy synthesis of 2-aryl-3,3-dichloroazetidines, a rather unexplored class of azaheterocycles, is described. The title compounds were easily obtained by reduction of the corresponding 4-aryl-3,3dichloro-2-azetidinones with monochloroalane, which in turn were synthesized by a ketene-imine [2 + 2] cycloaddition. The reactivity of 3,3-dichloroazetidines with bases was investigated, yielding 2-[dimethoxy(aryl)methyl]aziridines by ring contraction when treated with sodium methoxide. Furthermore, reacting the 3,3-dichloroazetidines with sodium hydride in DMSO, followed by aqueous workup, afforded 1-alkyl-2-aroylaziridines, by hydrolysis of the intermediate 2-azetines and ring closure of the transient 3-amino-2-chloro-1-phenyl-1-propanone derivatives. Monitoring this reaction in an NMR tube, using sodium hydride in DMSO-d(6),, allowed the characterization of the intermediate strained heterocyclic enamines, i.e., 2-azetines, by H-1 and C-13 NMR.