(S)-tert-butyl N-(1-(4-bromophenyl)-2,2-difluoro-3-oxo-3-phenylpropyl)carbamate | 1277192-05-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (S)-tert-butyl N-(1-(4-bromophenyl)-2,2-difluoro-3-oxo-3-phenylpropyl)carbamate
• 英文别名: tert-butyl N-[(1S)-1-(4-bromophenyl)-2,2-difluoro-3-oxo-3-phenylpropyl]carbamate
• CAS: 1277192-05-8
• 化学式: C₂₀H₂₀BrF₂NO₃
• 分子量: 440.285
• InChiKey: AZYWEEPNRBHKMT-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl N-(1-(4-bromophenyl)-2,2-difluoro-3-oxo-3-phenylpropyl)carbamate 在 吡啶 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (S)-N-(1-(4-bromophenyl)-2,2-difluoro-3-oxo-3-phenylpropyl)benzamide
  参考文献：
  名称：

  Chiral Phosphoric Acid Catalyzed Enantioselective Synthesis of β-Amino-α,α-difluoro Carbonyl Compounds

  摘要：

  A biphenol-based chiral phosphoric acid bearing a 9-anthryl group at each of the 3,3'-positions catalyzed the asymmetric Mannich-type reaction of N-Boc Imine with difluoroenol silyl ethers In the presence of MS3A In THF to afford beta-amino-alpha,alpha-difluoroketones In good yields and with excellent enantioselectivities. Optically pure 3,3-difluoroazetidin-2-one was readily synthesized from the Mannich-adduct.

  DOI：

  10.1021/ol200374m
• 作为产物：
  描述：

  tert-butyl 4-bromobenzylidenecarbamate 、 2,2-difluoro-1-phenyl-1-trimethylsiloxyethene 在 (S)-3,3'-bis(9-anthracenyl)-6,6'-dimethyl-1,1'-biphenyl-2,2'-phosphate 作用下， 以 四氢呋喃 为溶剂， 反应 23.0h， 以74%的产率得到(S)-tert-butyl N-(1-(4-bromophenyl)-2,2-difluoro-3-oxo-3-phenylpropyl)carbamate
  参考文献：
  名称：

  Chiral Phosphoric Acid Catalyzed Enantioselective Synthesis of β-Amino-α,α-difluoro Carbonyl Compounds

  摘要：

  A biphenol-based chiral phosphoric acid bearing a 9-anthryl group at each of the 3,3'-positions catalyzed the asymmetric Mannich-type reaction of N-Boc Imine with difluoroenol silyl ethers In the presence of MS3A In THF to afford beta-amino-alpha,alpha-difluoroketones In good yields and with excellent enantioselectivities. Optically pure 3,3-difluoroazetidin-2-one was readily synthesized from the Mannich-adduct.

  DOI：

  10.1021/ol200374m

文献信息

• Chiral Phosphoric Acid Catalyzed Enantioselective Synthesis of β-Amino-α,α-difluoro Carbonyl Compounds
  作者：Wataru Kashikura、Keiji Mori、Takahiko Akiyama

  DOI：10.1021/ol200374m

  日期：2011.4.1

  A biphenol-based chiral phosphoric acid bearing a 9-anthryl group at each of the 3,3'-positions catalyzed the asymmetric Mannich-type reaction of N-Boc Imine with difluoroenol silyl ethers In the presence of MS3A In THF to afford beta-amino-alpha,alpha-difluoroketones In good yields and with excellent enantioselectivities. Optically pure 3,3-difluoroazetidin-2-one was readily synthesized from the Mannich-adduct.