N-benzyl-2,2-difluoro-4-(thiophen-3-yl)-3-butynamide | 957109-33-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-benzyl-2,2-difluoro-4-(thiophen-3-yl)-3-butynamide
• 英文别名: N-benzyl-2,2-difluoro-4-thiophen-3-ylbut-3-ynamide
• CAS: 957109-33-0
• 化学式: C₁₅H₁₁F₂NOS
• 分子量: 291.321
• InChiKey: ZGVBMDIBCVVQIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  57.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyl-2,2-difluoro-4-(thiophen-3-yl)-3-butynamide 在 盐酸 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 N-benzyl-2,2-difluoro-4-oxo-4-(thiophen-3-yl)butanamide
  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：

  1-bromo-1,1-difluoro-3-(thiophen-3-yl)-2-propyne 在 碘 、 sodium hydride 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 N-benzyl-2,2-difluoro-4-(thiophen-3-yl)-3-butynamide
  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

• 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.