(2R,4R,5S,6R,7R)-4-Acetyl-5-methanesulfonyloxy-7-methoxy-8-oxo-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid methyl ester | 780782-09-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,4R,5S,6R,7R)-4-Acetyl-5-methanesulfonyloxy-7-methoxy-8-oxo-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,4R,5S,6R,7R)-4-acetyl-7-methoxy-5-methylsulfonyloxy-8-oxo-1-azabicyclo[4.2.0]octane-2-carboxylate
• CAS: 780782-09-4
• 化学式: C₁₃H₁₉NO₈S
• 分子量: 349.362
• InChiKey: WAQQLNHVHMXMHU-HPENLJRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,4R,5S,6R,7R)-4-Acetyl-5-methanesulfonyloxy-7-methoxy-8-oxo-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid methyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 反应 0.5h， 以100%的产率得到(2R,6S,7R)-4-Acetyl-7-methoxy-8-oxo-1-aza-bicyclo[4.2.0]oct-4-ene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Access to enantiopure polycyclic β-lactams by Diels–Alder reaction of novel inner-outer-ring 2-(silyloxy)dienes with a carbacepham skeleton

  摘要：

  The synthesis of unprecedented inner-outer-ring 2-[tert-butyidimethylsilyloxy]dienes with a carbacepham structure in optically pure form and their totally pi-facial endo selective Diels-Alder reactions to structurally novel polycyclic beta-lactams is reported. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2004.08.022
• 作为产物：
  描述：

  (2R,4S,5S,6S,7R)-5-Hydroxy-4-isopropenyl-7-methoxy-8-oxo-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid methyl ester 在 ruthenium trichloride 、 sodium periodate 、 三乙胺 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 生成 (2R,4R,5S,6R,7R)-4-Acetyl-5-methanesulfonyloxy-7-methoxy-8-oxo-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Access to enantiopure polycyclic β-lactams by Diels–Alder reaction of novel inner-outer-ring 2-(silyloxy)dienes with a carbacepham skeleton

  摘要：

  The synthesis of unprecedented inner-outer-ring 2-[tert-butyidimethylsilyloxy]dienes with a carbacepham structure in optically pure form and their totally pi-facial endo selective Diels-Alder reactions to structurally novel polycyclic beta-lactams is reported. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2004.08.022

文献信息

• Access to enantiopure polycyclic β-lactams by Diels–Alder reaction of novel inner-outer-ring 2-(silyloxy)dienes with a carbacepham skeleton
  作者：Benito Alcaide、Rosa M. de Murga、Carmen Pardo、Carolina Rodríguez-Ranera

  DOI：10.1016/j.tetlet.2004.08.022

  日期：2004.9

  The synthesis of unprecedented inner-outer-ring 2-[tert-butyidimethylsilyloxy]dienes with a carbacepham structure in optically pure form and their totally pi-facial endo selective Diels-Alder reactions to structurally novel polycyclic beta-lactams is reported. (C) 2004 Published by Elsevier Ltd.