(3'S)-1-[3'-(4-methoxybenzyloxy)-2'-methylenebutyl]-4-vinyloxyazetidin-2-one | 606972-07-0

• 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: (3'S)-1-[3'-(4-methoxybenzyloxy)-2'-methylenebutyl]-4-vinyloxyazetidin-2-one
• 英文别名: 4-ethenoxy-1-[(3S)-3-[(4-methoxyphenyl)methoxy]-2-methylidenebutyl]azetidin-2-one
• CAS: 606972-07-0
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: JELMHQUVHQWHQE-PIVQAISJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3'S)-1-[3'-(4-methoxybenzyloxy)-2'-methylenebutyl]-4-vinyloxyazetidin-2-one 在 silica gel 、 四氯化锡 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 6.17h， 生成 (3'S)-4-acetoxy-1'-[3'-hydroxy-2'-methylenebut-1'-yl]azetidin-2-one
  参考文献：
  名称：

  A new synthetic approach to 5-dethia-4-methyl-5-oxacephems

  摘要：

  Starting from (L)-ethyl lactate and 4-vinyloxy-azetidin-2-one the diastereomeric (4S,6R)- and (4S,6S)-4-methyl-5-oxa-3-methylene and 3-oxo-cephams were obtained. The formation of the cepham skeleton proceeds with a diastereomeric excess up to 80%, depending on catalyst and reaction conditions. For comparison, the corresponding racemic cephams lacking a methyl at C-4 or with a gem-dimethyl group at C-4 were synthesized. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00939-6
• 作为产物：
  描述：

  (3S)-1-bromo-3-(p-methoxybenzyloxy)butan-2-one 在 咪唑 、 正丁基锂 、 溴 、 四丁基硫酸氢铵 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.17h， 生成 (3'S)-1-[3'-(4-methoxybenzyloxy)-2'-methylenebutyl]-4-vinyloxyazetidin-2-one
  参考文献：
  名称：

  A new synthetic approach to 5-dethia-4-methyl-5-oxacephems

  摘要：

  Starting from (L)-ethyl lactate and 4-vinyloxy-azetidin-2-one the diastereomeric (4S,6R)- and (4S,6S)-4-methyl-5-oxa-3-methylene and 3-oxo-cephams were obtained. The formation of the cepham skeleton proceeds with a diastereomeric excess up to 80%, depending on catalyst and reaction conditions. For comparison, the corresponding racemic cephams lacking a methyl at C-4 or with a gem-dimethyl group at C-4 were synthesized. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00939-6

文献信息

• A new synthetic approach to 5-dethia-4-methyl-5-oxacephems
  作者：Zbigniew Kałuża、Arkadiusz Kazimierski、Krzysztof Lewandowski、Kinga Suwińska、Beata Szczȩsna、Marek Chmielewski

  DOI：10.1016/s0040-4020(03)00939-6

  日期：2003.7

  Starting from (L)-ethyl lactate and 4-vinyloxy-azetidin-2-one the diastereomeric (4S,6R)- and (4S,6S)-4-methyl-5-oxa-3-methylene and 3-oxo-cephams were obtained. The formation of the cepham skeleton proceeds with a diastereomeric excess up to 80%, depending on catalyst and reaction conditions. For comparison, the corresponding racemic cephams lacking a methyl at C-4 or with a gem-dimethyl group at C-4 were synthesized. (C) 2003 Elsevier Ltd. All rights reserved.