(4R)-1-[(1S,2R)-2-methoxy-1,2-diphenylethyl]-3,3-dimethyl-4-phenylazetidin-2-one | 270077-78-6

• 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: (4R)-1-[(1S,2R)-2-methoxy-1,2-diphenylethyl]-3,3-dimethyl-4-phenylazetidin-2-one
• CAS: 270077-78-6
• 化学式: C₂₆H₂₇NO₂
• 分子量: 385.506
• InChiKey: VMNRTCGTPPMMPP-RBZQAINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R)-1-[(1S,2R)-2-methoxy-1,2-diphenylethyl]-3,3-dimethyl-4-phenylazetidin-2-one 在 potassium tert-butylate 、 间氯过氧苯甲酸 、 calcium hypochlorite 、 溶剂黄146 作用下， 以 二甲基亚砜 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 21.5h， 生成 (R)-3-Benzoylamino-2,2-dimethyl-3-phenyl-propionic acid
  参考文献：
  名称：

  Stereoselective Synthesis of Optically Active b-Lactams by the Reaction of Chiral Imines Derived from erythro-2-Amino-1,2-diphenylethanol with Ester Enolates

  摘要：

  Chiral imines, derived from (1S,2R)-2-methoxy-1,2-diphenylethylamine and aromatic aldehydes, reacted with ester enolates prepared from ketene silyl acetals and methyllithium to give beta-lactams in good yields with high diastereoselectivity. This method provides a useful and simple route for the construction of optically active beta-lactam skeletons.

  DOI：

  10.3987/com-99-s95
• 作为产物：
  描述：

  1-甲氧基-1-(三甲基甲硅氧基)-2-甲基-1-丙烯 、 (1S,2R)-N-benzylidene-2-methoxy-1,2-diphenylethylamine 在 甲基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 25.0h， 以81%的产率得到(4R)-1-[(1S,2R)-2-methoxy-1,2-diphenylethyl]-3,3-dimethyl-4-phenylazetidin-2-one
  参考文献：
  名称：

  Stereoselective Synthesis of Optically Active b-Lactams by the Reaction of Chiral Imines Derived from erythro-2-Amino-1,2-diphenylethanol with Ester Enolates

  摘要：

  Chiral imines, derived from (1S,2R)-2-methoxy-1,2-diphenylethylamine and aromatic aldehydes, reacted with ester enolates prepared from ketene silyl acetals and methyllithium to give beta-lactams in good yields with high diastereoselectivity. This method provides a useful and simple route for the construction of optically active beta-lactam skeletons.

  DOI：

  10.3987/com-99-s95

文献信息

• Stereoselective Synthesis of Optically Active b-Lactams by the Reaction of Chiral Imines Derived from erythro-2-Amino-1,2-diphenylethanol with Ester Enolates
  作者：Yukihiko Hashimoto、Tsuneo Ogasawara、Minoru Hayashi、Kazuhiko Saigo

  DOI：10.3987/com-99-s95

  日期：——

  Chiral imines, derived from (1S,2R)-2-methoxy-1,2-diphenylethylamine and aromatic aldehydes, reacted with ester enolates prepared from ketene silyl acetals and methyllithium to give beta-lactams in good yields with high diastereoselectivity. This method provides a useful and simple route for the construction of optically active beta-lactam skeletons.