(1S,8aS,8bR)-1-((R)-1-Hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid allyl ester | 135557-10-7

• 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: (1S,8aS,8bR)-1-((R)-1-Hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid allyl ester
• 英文别名: prop-2-enyl (1S,8aS,8bR)-1-[(1R)-1-hydroxyethyl]-2-oxo-5,6,7,8,8a,8b-hexahydro-1H-azeto[1,2-b]isoindole-4-carboxylate
• CAS: 135557-10-7
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: FTACTXUMPMEHHD-LYIQGSDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,8aS,8bR)-1-((R)-1-Hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid allyl ester 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到(8aS,8bR)-1-Eth-(E)-ylidene-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid allyl ester
  参考文献：
  名称：

  Design, synthesis and bioactivity evaluation of tribactam β lactamase inhibitors

  摘要：

  Known carbapenem compounds with inhibitory effect towards P-lactamase enzymes are formed from bicyclical beta lactam structural scaffolds. On the basis of results from theoretical computational methods and molecular modelling we have designed and developed a synthetic route towards novel, biologically active tricyclic derivatives of carbapenems. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00061-6
• 作为产物：
  描述：

  4-乙酰氧基氮杂环丁酮 在 二氯甲烷 、 四丁基氟化铵 、 溶剂黄146 、 三乙胺 、 对苯二酚 、 zinc(II) iodide 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 (1S,8aS,8bR)-1-((R)-1-Hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid allyl ester
  参考文献：
  名称：

  Design, synthesis and bioactivity evaluation of tribactam β lactamase inhibitors

  摘要：

  Known carbapenem compounds with inhibitory effect towards P-lactamase enzymes are formed from bicyclical beta lactam structural scaffolds. On the basis of results from theoretical computational methods and molecular modelling we have designed and developed a synthetic route towards novel, biologically active tricyclic derivatives of carbapenems. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00061-6

文献信息

• Design, synthesis and bioactivity evaluation of tribactam β lactamase inhibitors
  作者：Anton Copar、Tadeja Prevec、Borut Anžič、Tomaž Mesar、Lovro Selič、Mateja Vilar、Tom Solmajer

  DOI：10.1016/s0960-894x(02)00061-6

  日期：2002.3

  Known carbapenem compounds with inhibitory effect towards P-lactamase enzymes are formed from bicyclical beta lactam structural scaffolds. On the basis of results from theoretical computational methods and molecular modelling we have designed and developed a synthetic route towards novel, biologically active tricyclic derivatives of carbapenems. (C) 2002 Elsevier Science Ltd. All rights reserved.