(3R,4R)-3-ethyl-4-(4-methoxyphenyl)-3-phenyl-1-tosylazetidin-2-one | 1365086-62-9

• 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: (3R,4R)-3-ethyl-4-(4-methoxyphenyl)-3-phenyl-1-tosylazetidin-2-one
• 英文别名: (3R,4R)-3-ethyl-4-(4-methoxyphenyl)-1-(4-methylphenyl)sulfonyl-3-phenylazetidin-2-one
• CAS: 1365086-62-9
• 化学式: C₂₅H₂₅NO₄S
• 分子量: 435.544
• InChiKey: PIMSEECITFLCSW-ILBGXUMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-苯基-1-丁烯-1-酮 、 N-(4-甲氧基亚苄基)-4-甲基苯磺酰胺 在 (R,R)-binaphane 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 (3S,4S)-3-ethyl-4-(4-methoxyphenyl)-3-phenyl-1-tosylazetidin-2-one 、 (3R,4R)-3-ethyl-4-(4-methoxyphenyl)-3-phenyl-1-tosylazetidin-2-one
  参考文献：
  名称：

  BINAPHANE-Catalyzed Asymmetric Synthesis of trans-β-Lactams from Disubstituted Ketenes and N-Tosyl Arylimines

  摘要：

  The development of a BINAPHANE-catalyzed formal [2 + 2]-cycloaddition of disubstituted ketenes and inexpensive N-tosyl arylimines that provides access to a variety of highly substituted beta-lactams (16 examples) is described. The BINAPHANE catalytic system displays moderate to excellent enantioselectivity (up to 98% ee) and high diastereoselectivity in most cases, favoring formation of the trans-diastereomer (13 examples with >= 90:10).

  DOI：

  10.1021/ol3003783

文献信息

• BINAPHANE-Catalyzed Asymmetric Synthesis of <i>trans</i>-β-Lactams from Disubstituted Ketenes and <i>N</i>-Tosyl Arylimines
  作者：Shi Chen、Eric C. Salo、Kraig A. Wheeler、Nessan J. Kerrigan

  DOI：10.1021/ol3003783

  日期：2012.4.6

  The development of a BINAPHANE-catalyzed formal [2 + 2]-cycloaddition of disubstituted ketenes and inexpensive N-tosyl arylimines that provides access to a variety of highly substituted beta-lactams (16 examples) is described. The BINAPHANE catalytic system displays moderate to excellent enantioselectivity (up to 98% ee) and high diastereoselectivity in most cases, favoring formation of the trans-diastereomer (13 examples with >= 90:10).