(3S,4R)-4-(4-bromophenyl)-3-(4-methoxyphenyl)-1-tosylazetidin-2-one | 1556906-26-3

• 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: (3S,4R)-4-(4-bromophenyl)-3-(4-methoxyphenyl)-1-tosylazetidin-2-one
• 英文别名: (3S,4R)-4-(4-bromophenyl)-3-(4-methoxyphenyl)-1-(4-methylphenyl)sulfonylazetidin-2-one
• CAS: 1556906-26-3
• 化学式: C₂₃H₂₀BrNO₄S
• 分子量: 486.386
• InChiKey: BEQQIFKJRWBNKI-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  4-甲氧基苯乙酸酐 、 (E)-N-(4-溴苯亚甲基)-4-甲基苯磺酰胺 在 (2S,3R)-3,4-二氢-3-异丙基-2-苯基-2H-嘧啶并[2,1-b]苯并噻唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以86%的产率得到
  参考文献：
  名称：

  Isothiourea-Catalyzed Asymmetric Synthesis of β-Lactams and β-Amino Esters from Arylacetic Acid Derivatives and N-Sulfonylaldimines

  摘要：

  The isothiourea HBTM-2.1 (5 mol %) catalyzes the asymmetric formal [2 + 2] cycloaddition of both arylacetic acids (following activation with tosyl chloride) and preformed 2-arylacetic anhydrides with N-sulfonylaldimines, generating stereo-defined 2,3-diaryl-beta-amino esters (after ring-opening) and 3,4-diaryl-anti-beta-lactams, respectively, with high diastereocontrol (up to >95:5 dr) and good to excellent enantiocontrol. Deprotection of the N-tosyl substituent within the beta-lactam framework was possible without racemization by treatment with SmI2.

  DOI：

  10.1021/jo402590m

文献信息

• Isothiourea-Catalyzed Asymmetric Synthesis of β-Lactams and β-Amino Esters from Arylacetic Acid Derivatives and <i>N</i>-Sulfonylaldimines
  作者：Siobhan R. Smith、James Douglas、Hugues Prevet、Peter Shapland、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1021/jo402590m

  日期：2014.2.21

  The isothiourea HBTM-2.1 (5 mol %) catalyzes the asymmetric formal [2 + 2] cycloaddition of both arylacetic acids (following activation with tosyl chloride) and preformed 2-arylacetic anhydrides with N-sulfonylaldimines, generating stereo-defined 2,3-diaryl-beta-amino esters (after ring-opening) and 3,4-diaryl-anti-beta-lactams, respectively, with high diastereocontrol (up to >95:5 dr) and good to excellent enantiocontrol. Deprotection of the N-tosyl substituent within the beta-lactam framework was possible without racemization by treatment with SmI2.