3,3-difluoro-1-(4-methoxyphenyl)-5-phenyl-1H-pyrrol-2(3H)-one | 957109-38-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 3,3-difluoro-1-(4-methoxyphenyl)-5-phenyl-1H-pyrrol-2(3H)-one
• 英文别名: 3,3-Difluoro-1-(4-methoxyphenyl)-5-phenylpyrrol-2-one；3,3-difluoro-1-(4-methoxyphenyl)-5-phenylpyrrol-2-one
• CAS: 957109-38-5
• 化学式: C₁₇H₁₃F₂NO₂
• 分子量: 301.293
• InChiKey: NNTWIKWUIUTSBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3-difluoro-1-(4-methoxyphenyl)-5-phenyl-1H-pyrrol-2(3H)-one 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以66%的产率得到2,2-difluoro-N-(4-methoxyphenyl)-4-oxo-4-phenylbutanamide
  参考文献：
  名称：

  Intramolecular Hydroamination of Difluoropropargyl Amides:  Regioselective Synthesis of Fluorinated β- and γ-Lactams

  摘要：

  Functionalized gem-difluoro beta- and gamma-lactams were synthesized through a novel intramolecular hydroamination reaction of difluoropropargyl amides.beta-Lactams were obtained via a Baldwin disfavored 4-exo-digonal cyclization using palladium acetate as the catalyst, whereas gamma-lactams were produced under basic conditions. Acid hydration of gamma-lactams produced ketoamides or hemiaminals selectively.

  DOI：

  10.1021/ol701811z
• 作为产物：
  描述：

  methyl 2,2-difluoro-4-phenyl-3-butynoate 在 四丁基氟化铵 、 三甲基铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 3,3-difluoro-1-(4-methoxyphenyl)-5-phenyl-1H-pyrrol-2(3H)-one
  参考文献：
  名称：

  Intramolecular Hydroamination of Difluoropropargyl Amides:  Regioselective Synthesis of Fluorinated β- and γ-Lactams

  摘要：

  Functionalized gem-difluoro beta- and gamma-lactams were synthesized through a novel intramolecular hydroamination reaction of difluoropropargyl amides.beta-Lactams were obtained via a Baldwin disfavored 4-exo-digonal cyclization using palladium acetate as the catalyst, whereas gamma-lactams were produced under basic conditions. Acid hydration of gamma-lactams produced ketoamides or hemiaminals selectively.

  DOI：

  10.1021/ol701811z

文献信息

• Cu-Catalyzed Aminodifluoroalkylation of Alkynes and α-Bromodifluoroacetamides
  作者：Yunhe Lv、Weiya Pu、Qian Chen、Qingqing Wang、Jiejie Niu、Qian Zhang

  DOI：10.1021/acs.joc.7b01313

  日期：2017.8.4

  The copper-catalyzed highly regioselective aminodifluoroalkylation of alkynes and α-bromodifluoroacetamides was realized for the first time. With this method, 3,3-difluoro-1H-pyrrol-2(3H)-ones were constructed in a single step from various alkynes and α-bromodifluoroacetamides substrates without using any extra oxidant.

  首次实现了铜的炔烃和α-溴二氟乙酰胺的高区域选择性氨基二氟烷基化反应。用这种方法，可以在不使用任何氧化剂的情况下，由各种炔烃和α-溴二氟乙酰胺底物一步一步制得3，3-二氟-1 H-吡咯-2（3 H）-一。