(3R,4S)-3-benzyloxy-1-(2-bromo-2-propenyl)-4-hydroxymethylazetidin-2-one | 1415505-76-8

• 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)-3-benzyloxy-1-(2-bromo-2-propenyl)-4-hydroxymethylazetidin-2-one
• CAS: 1415505-76-8
• 化学式: C₁₄H₁₆BrNO₃
• 分子量: 326.19
• InChiKey: AIELQSWKBHSRQU-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3-benzyloxy-1-(2-bromo-2-propenyl)-4-hydroxymethylazetidin-2-one 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以82%的产率得到(3R,4S)-3-benzyloxy-1-(2,2,3-tribromopropyl)-4-hydroxymethylazetidin-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
• 作为产物：
  描述：

  1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-N-prop-2-enylmethanimine 在 sodium periodate 、 溴 、 碳酸氢钠 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 23.0h， 生成 (3R,4S)-3-benzyloxy-1-(2-bromo-2-propenyl)-4-hydroxymethylazetidin-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