3,3-dichloro-1-isopropyl-4-(4-methylphenyl)-2-azetidinone | 418765-64-7

• 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-methylphenyl)-2-azetidinone
• 英文别名: 3,3-Dichloro-4-(4-methylphenyl)-1-propan-2-ylazetidin-2-one
• CAS: 418765-64-7
• 化学式: C₁₃H₁₅Cl₂NO
• 分子量: 272.174
• InChiKey: NVFPYNJWQYGWCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,3-dichloro-1-isopropyl-4-(4-methylphenyl)-2-azetidinone 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以82%的产率得到3,3-dichloro-1-isopropyl-2-(4-methylphenyl)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 、 isopropyl-[(4-methylphenyl)meth-(E)ylidene]amine 在 三乙胺 作用下， 以 苯 为溶剂， 反应 1.0h， 以70%的产率得到3,3-dichloro-1-isopropyl-4-(4-methylphenyl)-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

• The Halogen-Lithium Exchange Reaction of 3,3-Dichloro-2-azetidinones: Application to the Synthesis of<b> <i>cis</i> </b>-4-Aryl-3-chloro-2-azetidinones
  作者：Norbert De Kimpe、Yves Dejaegher、Bram Denolf、Christian V. Stevens

  DOI：10.1055/s-2004-831248

  日期：——

  A straightforward synthesis of new cis-4-aryl-3-chloro-2-azetidinones was developed, using a halogen-lithium exchange reaction on 4-aryl-3,3-dichloro-2-azetidinones. This methodology was further extended to the use of alkyl halides as electrophiles, while more complex electrophiles could not be introduced.

  使用 4-aryl-3,3-dichloro-2-azetidinones 上的卤素-锂交换反应，开发了一种直接合成新的 cis-4-aryl-3-chloro-2-azetidinones 的方法。该方法进一步扩展到使用烷基卤化物作为亲电体，而无法引入更复杂的亲电体。
• 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.