(4S,5R,6S)-3-[(E)-2-((S)-1-Allyloxycarbonyl-pyrrolidin-2-yl)-vinyl]-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester | 126407-89-4

• 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: (4S,5R,6S)-3-[(E)-2-((S)-1-Allyloxycarbonyl-pyrrolidin-2-yl)-vinyl]-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
• 英文别名: prop-2-enyl (4S,5R,6S)-6-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-methyl-7-oxo-3-[(E)-2-[(2S)-1-prop-2-enoxycarbonylpyrrolidin-2-yl]ethenyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 126407-89-4
• 化学式: C₂₉H₄₄N₂O₆Si
• 分子量: 544.764
• InChiKey: RYLPOIMQOPTYOH-HNWFZMLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,5R,6S)-3-[(E)-2-((S)-1-Allyloxycarbonyl-pyrrolidin-2-yl)-vinyl]-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester 在 (Ph₃)4Pd⁽⁰⁾ 四丁基氟化铵 、 5,5-二甲基-1,3-环己二酮 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 (4S,5R,6S)-6-[(1R)-1-Hydroxyethyl]-4-methyl-7-oxo-3-[(E)-2{(2S)-pyrrolidin-2-yl}ethenyl]-1-azabicyclo-[3.2.0]hept-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2-vinyl carbapenems. Remarkable DHP-1 stability of 1′-substituted analogs

  摘要：

  The synthesis, antibacterial activity and DHP-susceptibility of a series of novel 2-vinyl carbapenems is described. Carbapenems having a 1'-substituted vinyl moiety at the 2 position were found to be very stable toward DHP-1, displaying comparable stability to compounds with a 1 beta-methyl functionality. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00495-7
• 作为产物：
  描述：

  (4S,5R,6S)-3-[2-((S)-1-Allyloxycarbonyl-pyrrolidin-2-yl)-2-methanesulfonyloxy-ethyl]-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (4S,5R,6S)-3-[(E)-2-((S)-1-Allyloxycarbonyl-pyrrolidin-2-yl)-vinyl]-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2-vinyl carbapenems. Remarkable DHP-1 stability of 1′-substituted analogs

  摘要：

  The synthesis, antibacterial activity and DHP-susceptibility of a series of novel 2-vinyl carbapenems is described. Carbapenems having a 1'-substituted vinyl moiety at the 2 position were found to be very stable toward DHP-1, displaying comparable stability to compounds with a 1 beta-methyl functionality. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00495-7