anti-3-fluoro-1,3,4-triphenylazetidin-2-one | 138203-03-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: anti-3-fluoro-1,3,4-triphenylazetidin-2-one
• 英文别名: (3R,4S)-3-fluoro-1,3,4-triphenylazetidin-2-one
• CAS: 138203-03-9；138203-04-0
• 化学式: C₂₁H₁₆FNO
• 分子量: 317.363
• InChiKey: HESLTCICQLJDPN-PZJWPPBQSA-N

物化性质

• 沸点：
  495.9±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-fluoro-2-phenylacetyl chloride 、 N-苄叉苯胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以51%的产率得到anti-3-fluoro-1,3,4-triphenylazetidin-2-one
  参考文献：
  名称：

  The stereoselective synthesis of 3-fluoro-azetidinones

  摘要：

  3-Fluoro-azetidinones were prepared by both the enolate-imine and ketene-imine condensation reactions. The reactions of fluorinated ketenes with imines were remarkably stereoselective forming products derived from lk reaction topicity.

  DOI：

  10.1016/0040-4039(91)80058-e

文献信息

• Ni-catalyzed α-arylation of secondary α-bromo-α-fluoro-β-lactam: cross-coupling of a secondary fluorine-containing electrophile
  作者：Atsushi Tarui、Shoji Kondo、Kazuyuki Sato、Masaaki Omote、Hideki Minami、Yoshihisa Miwa、Akira Ando

  DOI：10.1016/j.tet.2012.12.002

  日期：2013.2

  A highly diastereoselective cross-coupling reaction of an α-bromo-α-fluoro-β-lactam with a wide range of aryl Grignard reagents was catalyzed by Ni/bis(oxazoline) in yields of up to 98%. The product was obtained diastereoselectively as an anti-isomer. This is the first successful α-arylation of an α-fluoro-β-lactam to produce diverse α-aryl-α-fluoro-β-lactams.

  Ni /双（恶唑啉）催化α-溴-α-氟-β-内酰胺与多种芳基格氏试剂的高度非对映选择性交叉偶联反应，收率高达98％。非对映选择性地获得该产物作为反异构体。这是α-氟-β-内酰胺成功生产出多种α-芳基-α-氟-β-内酰胺的第一个成功的α-芳基化反应。
• The stereoselective synthesis of 3-fluoro-azetidinones
  作者：Koichi Araki、John A. Wichtowski、John T. Welch

  DOI：10.1016/0040-4039(91)80058-e

  日期：1991.9

  3-Fluoro-azetidinones were prepared by both the enolate-imine and ketene-imine condensation reactions. The reactions of fluorinated ketenes with imines were remarkably stereoselective forming products derived from lk reaction topicity.