2,2-difluoro-4-phenyl-N-[(S)-1-phenylethyl]-3-butynamide | 957109-31-8

• 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: 2,2-difluoro-4-phenyl-N-[(S)-1-phenylethyl]-3-butynamide
• 英文别名: 2,2-difluoro-4-phenyl-N-[(1S)-1-phenylethyl]but-3-ynamide
• CAS: 957109-31-8
• 化学式: C₁₈H₁₅F₂NO
• 分子量: 299.32
• InChiKey: RDPHCGOXBCUGMM-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-difluoro-4-phenyl-N-[(S)-1-phenylethyl]-3-butynamide 在 盐酸 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 2,2-difluoro-N-[(S)-1-phenylethyl]-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：

  bromodifluoromethylphenylacetylene 在 碘 、 三甲基铝 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 2,2-difluoro-4-phenyl-N-[(S)-1-phenylethyl]-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

• Regioselectivity in Intermolecular Pauson-Khand Reactions of Dissymmetric Fluorinated Alkynes
  作者：Jean-Claude Kizirian、Nuria Aiguabella、Albert Pesquer、Santos Fustero、Paula Bello、Xavier Verdaguer、Antoni Riera

  DOI：10.1021/ol102283c

  日期：2010.12.17

  Stoichiometric and catalytic intermolecular Pauson−Khand reactions (PKRs) of dissymmetric fluorinated alkynes were performed, affording regioselectively α-fluorinated cyclopentenones. Ethyl 4,4,4-trifluorobutynoate was an excellent substrate; its reaction with norbornadiene gave the corresponding PKR adduct in good yield and complete regioselectivity. Conjugate addition of nitroalkanes or cyanide to

  进行了不对称氟化炔的化学计量和催化分子间Pauson-Khand反应（PKR），提供了区域选择性的α-氟化环戊烯酮。4,4,4-三氟丁酸乙酯是极好的底物；其与降冰片二烯的反应以良好的产率和完全的区域选择性得到了相应的PKR加合物。向该加合物共轭添加硝基烷烃或氰化物是立体特异性的，并伴随着三氟甲基的损失。可以利用该反应制备具有四元中心的环戊烯酮。
• 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.