4-(allyloxy)-3,3-dichloro-1-isopropyl-4-(4-nitrophenyl)azetidin-2-one | 1252581-02-4

• 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: 4-(allyloxy)-3,3-dichloro-1-isopropyl-4-(4-nitrophenyl)azetidin-2-one
• 英文别名: 3,3-Dichloro-4-(4-nitrophenyl)-1-propan-2-yl-4-prop-2-enoxyazetidin-2-one
• CAS: 1252581-02-4
• 化学式: C₁₅H₁₆Cl₂N₂O₄
• 分子量: 359.209
• InChiKey: VFLJQMVUEDVXTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(allyloxy)-3,3-dichloro-1-isopropyl-4-(4-nitrophenyl)azetidin-2-one 在 五甲基二乙烯三胺 、 copper(l) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 以79%的产率得到3-chloro-4-chloromethyl-1-isopropyl-6-(4-nitrophenyl)tetrahydrofuro[3,2-c]azetidin-2-one
  参考文献：
  名称：

  Synthesis of Chlorinated Bicyclic C-Fused Tetrahydrofuro[3,2-c]azetidin-2-ones

  摘要：

  Some bicyclic C-fused chlorinated tetrahydrofuro[3,2-c]azetidin-2-ones were prepared by a fairly general route involving Staudinger reaction of allylic/propargylic imidates with dichloroketene followed by highly diastereoselective CuCl/PMDETA-catalyzed 5-exo-trig/dig chlorine atom transfer radical cyclization. An oxepan-fused beta-lactam was also prepared similarly by 7-endo-trig cyclization. Synthetic application of the side chain chlorine atom of the products was demonstrated by its substitution in one of the products with azide followed by azide-alkyne click reaction with phenylacetylene to obtain a 1,2,3-triazolyltetrahydrofuro[3,2-c]azetidin-2-one.

  DOI：

  10.1021/jo101045z
• 作为产物：
  描述：

  二氯乙酰氯 、 allyl N-isopropyl-4-nitrobenzimidate 在 三乙胺 作用下， 以 苯 为溶剂， 反应 2.25h， 以78%的产率得到4-(allyloxy)-3,3-dichloro-1-isopropyl-4-(4-nitrophenyl)azetidin-2-one
  参考文献：
  名称：

  Synthesis of Chlorinated Bicyclic C-Fused Tetrahydrofuro[3,2-c]azetidin-2-ones

  摘要：

  Some bicyclic C-fused chlorinated tetrahydrofuro[3,2-c]azetidin-2-ones were prepared by a fairly general route involving Staudinger reaction of allylic/propargylic imidates with dichloroketene followed by highly diastereoselective CuCl/PMDETA-catalyzed 5-exo-trig/dig chlorine atom transfer radical cyclization. An oxepan-fused beta-lactam was also prepared similarly by 7-endo-trig cyclization. Synthetic application of the side chain chlorine atom of the products was demonstrated by its substitution in one of the products with azide followed by azide-alkyne click reaction with phenylacetylene to obtain a 1,2,3-triazolyltetrahydrofuro[3,2-c]azetidin-2-one.

  DOI：

  10.1021/jo101045z

文献信息

• Synthesis of Chlorinated Bicyclic C-Fused Tetrahydrofuro[3,2-<i>c</i>]azetidin-2-ones
  作者：Ram N. Ram、Neeraj Kumar、Nem Singh

  DOI：10.1021/jo101045z

  日期：2010.11.5

  Some bicyclic C-fused chlorinated tetrahydrofuro[3,2-c]azetidin-2-ones were prepared by a fairly general route involving Staudinger reaction of allylic/propargylic imidates with dichloroketene followed by highly diastereoselective CuCl/PMDETA-catalyzed 5-exo-trig/dig chlorine atom transfer radical cyclization. An oxepan-fused beta-lactam was also prepared similarly by 7-endo-trig cyclization. Synthetic application of the side chain chlorine atom of the products was demonstrated by its substitution in one of the products with azide followed by azide-alkyne click reaction with phenylacetylene to obtain a 1,2,3-triazolyltetrahydrofuro[3,2-c]azetidin-2-one.