1-benzyl-3,3-difluoro-5-phenyl-1H-pyrrol-2(3H)-one | 957109-37-4

• 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: 1-benzyl-3,3-difluoro-5-phenyl-1H-pyrrol-2(3H)-one
• 英文别名: 1-Benzyl-3,3-difluoro-5-phenylpyrrol-2-one；1-benzyl-3,3-difluoro-5-phenylpyrrol-2-one
• CAS: 957109-37-4
• 化学式: C₁₇H₁₃F₂NO
• 分子量: 285.293
• InChiKey: ZGZPENKDRKGVAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 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：
  20.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-3,3-difluoro-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98%的产率得到2,2-difluoro-N-benzyl-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 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 1-benzyl-3,3-difluoro-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。
• Selective enhancement effects of silver salts on the transition metal-catalyzed synthesis of gem-difluorinated heterocyclics using 2,2-difluorohomopropargyl amides
  作者：Satoru Arimitsu、Rebecca L. Bottom、Gerald B. Hammond

  DOI：10.1016/j.jfluchem.2008.05.010

  日期：2008.10

  The addition of silver salts had an effect on the catalyst activity in the Pd(0)-catalyzed cyclization-coupling tandem reaction, as well as in the Rh(I)-catalyzed Pauson–Khand reaction. The cationic palladium complex generated from Pd(PPh3)4 (2.5 mol%) with AgSbF6 (1.5 equiv.) activates the triple bond of 2,2-difluoropropargylic amides to give the 4,5-disubstituted 3,3-difluoro-γ-lactams, through a

  银盐的添加对Pd（0）催化的环化偶联串联反应以及Rh（I）催化的Pauson-Khand反应的催化剂活性产生影响。由Pd（PPh 3）4（2.5 mol％）与AgSbF 6（1.5当量）生成的阳离子钯络合物激活2,2-二氟丙炔酰胺的三键，得到4,5-二取代的3,3-二氟- γ-内酰胺，通过顺序的5 -endo-dig环化和交叉偶联反应。硅胶色谱后，将γ-内酰胺转化为开环的单氟乙烯基化合物。含催化量的[Rh（COD）2 ] 2的氟化1,7-烯炔酰胺的Pauson-Khand反应（5mol％）和AgOTf（20mol％）得到相应的宝石-二氟化双环内酰胺。
• Intramolecular Hydroamination of Difluoropropargyl Amides:  Regioselective Synthesis of Fluorinated β- and γ-Lactams
  作者：Santos Fustero、Begoña Fernández、Paula Bello、Carlos del Pozo、Satoru Arimitsu、Gerald B. Hammond

  DOI：10.1021/ol701811z

  日期：2007.10.1

  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.