(3R,4S)-1-(2-bromo-2-propenyl)-4-[(1,1-dimethylethylamino)methyl]-3-phenoxyazetidin-2-one | 1415505-85-9

• 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: (3R,4S)-1-(2-bromo-2-propenyl)-4-[(1,1-dimethylethylamino)methyl]-3-phenoxyazetidin-2-one
• 英文别名: (3R,4S)-1-(2-bromoprop-2-enyl)-4-[(tert-butylamino)methyl]-3-phenoxyazetidin-2-one
• CAS: 1415505-85-9
• 化学式: C₁₇H₂₃BrN₂O₂
• 分子量: 367.286
• InChiKey: UNSPIKXAHMSATH-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (+)-(3R,4S)-4-formyl-3-phenoxy-1-(2-propenyl)-2-azetidinone 在 溴 、 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (3R,4S)-1-(2-bromo-2-propenyl)-4-[(1,1-dimethylethylamino)methyl]-3-phenoxyazetidin-2-one
  参考文献：
  名称：

  Asymmetric synthesis of 4-formyl-1-(ω-haloalkyl)-β-lactams and their transformation to functionalized piperazines and 1,4-diazepanes

  摘要：

  Chiral piperazine and 1,4-diazepane annulated beta-lactams, prepared from the corresponding (3R,4S)-4-imidoyl-1-(omega-haloalkyl)azetidin-2-ones through reduction with sodium borohydride in ethanol, were transformed into novel methyl (R)-alkoxy-[(S)-piperazin-2-yl]acetates and methyl (R)-alkoxy-[(S)-1,4-diazepan-2-yl]acetates upon treatment with hydrogen chloride in methanol. On the other hand, bromination of (3R,4R)-1-allyl-4-formyl-beta-lactams and (3R,4S)-1-allyl-4-imidoyl-beta-lactams in dichloromethane, followed by sodium borohydride reduction of the resulting dibrominated azetidin-2-ones in ethanol, did not afford the envisaged bicyclic beta-lactams but unexpectedly furnished (3R,4S)-1-(2-bromo-2-propenyl)azetidin-2-ones instead. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.136

文献信息

• Asymmetric synthesis of 4-formyl-1-(ω-haloalkyl)-β-lactams and their transformation to functionalized piperazines and 1,4-diazepanes
  作者：Stijn Dekeukeleire、Matthias D’hooghe、Matthieu Vanwalleghem、Willem Van Brabandt、Norbert De Kimpe

  DOI：10.1016/j.tet.2011.09.136

  日期：2012.12

  Chiral piperazine and 1,4-diazepane annulated beta-lactams, prepared from the corresponding (3R,4S)-4-imidoyl-1-(omega-haloalkyl)azetidin-2-ones through reduction with sodium borohydride in ethanol, were transformed into novel methyl (R)-alkoxy-[(S)-piperazin-2-yl]acetates and methyl (R)-alkoxy-[(S)-1,4-diazepan-2-yl]acetates upon treatment with hydrogen chloride in methanol. On the other hand, bromination of (3R,4R)-1-allyl-4-formyl-beta-lactams and (3R,4S)-1-allyl-4-imidoyl-beta-lactams in dichloromethane, followed by sodium borohydride reduction of the resulting dibrominated azetidin-2-ones in ethanol, did not afford the envisaged bicyclic beta-lactams but unexpectedly furnished (3R,4S)-1-(2-bromo-2-propenyl)azetidin-2-ones instead. (C) 2011 Elsevier Ltd. All rights reserved.