cis-1-(4'-methoxyphenyl)-3-chloro-3-phenylseleno-4-phenylazetidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: cis-1-(4'-methoxyphenyl)-3-chloro-3-phenylseleno-4-phenylazetidin-2-one
• 英文别名: (3S,4R)-3-chloro-1-(4-methoxyphenyl)-4-phenyl-3-phenylselanylazetidin-2-one
• 化学式: C₂₂H₁₈ClNO₂Se
• 分子量: 442.803
• InChiKey: MSTGVNNECPIRDK-IRLDBZIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  cis-1-(4'-methoxyphenyl)-3-chloro-3-phenylseleno-4-phenylazetidin-2-one 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到trans-1-(4'-methoxyphenyl)-3-chloro-3-phenylseleno-4-phenylazetidin-2-one
  参考文献：
  名称：

  Seleno-β-lactams: synthesis of monocyclic and spirocyclic selenoazetidin-2-ones

  摘要：

  An efficient protocol for the synthesis of novel seleno-beta-lactams using operationally simple strategies is presented. 3-Phenyl/benzylseleno-beta-lactams, obtained from 2-phenyl/benzylselenoethanoic acids, are transformed to cis-3-chloro-3-phenyl/benzylseleno-beta-lactams, which undergo reaction with various active aliphatic and aromatic substrates catalyzed by Lewis acid to produce cis-3-alkoxy-3-phenyl/ benzylseleno-beta-lactams and C-3 monosubstituted seleno-beta-lactams. Halogen mediated intraselenyl cyclization of cis-3-(prop-2-ynyloxy)3-benzylseleno-beta-lactams affords novel spiro seleno-beta-lactams. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.001
• 作为产物：
  描述：

  2-(phenylselanyl)acetic acid 在 N-氯代丁二酰亚胺 、 偶氮二异丁腈 、 三乙胺 、 三氯氧磷 作用下， 以 四氯化碳 、 苯 为溶剂， 生成 cis-1-(4'-methoxyphenyl)-3-chloro-3-phenylseleno-4-phenylazetidin-2-one
  参考文献：
  名称：

  Seleno-β-lactams: synthesis of monocyclic and spirocyclic selenoazetidin-2-ones

  摘要：

  An efficient protocol for the synthesis of novel seleno-beta-lactams using operationally simple strategies is presented. 3-Phenyl/benzylseleno-beta-lactams, obtained from 2-phenyl/benzylselenoethanoic acids, are transformed to cis-3-chloro-3-phenyl/benzylseleno-beta-lactams, which undergo reaction with various active aliphatic and aromatic substrates catalyzed by Lewis acid to produce cis-3-alkoxy-3-phenyl/ benzylseleno-beta-lactams and C-3 monosubstituted seleno-beta-lactams. Halogen mediated intraselenyl cyclization of cis-3-(prop-2-ynyloxy)3-benzylseleno-beta-lactams affords novel spiro seleno-beta-lactams. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.001

文献信息

• Seleno-β-lactams: synthesis of monocyclic and spirocyclic selenoazetidin-2-ones
  作者：Aman Bhalla、Paloth Venugopalan、Kuldip K. Bhasin、Shamsher S. Bari

  DOI：10.1016/j.tet.2007.02.001

  日期：2007.4

  An efficient protocol for the synthesis of novel seleno-beta-lactams using operationally simple strategies is presented. 3-Phenyl/benzylseleno-beta-lactams, obtained from 2-phenyl/benzylselenoethanoic acids, are transformed to cis-3-chloro-3-phenyl/benzylseleno-beta-lactams, which undergo reaction with various active aliphatic and aromatic substrates catalyzed by Lewis acid to produce cis-3-alkoxy-3-phenyl/ benzylseleno-beta-lactams and C-3 monosubstituted seleno-beta-lactams. Halogen mediated intraselenyl cyclization of cis-3-(prop-2-ynyloxy)3-benzylseleno-beta-lactams affords novel spiro seleno-beta-lactams. (c) 2007 Elsevier Ltd. All rights reserved.