(2R,6S,7R)-4-[1-(tert-Butyl-dimethyl-silanyloxy)-vinyl]-7-methoxy-8-oxo-1-aza-bicyclo[4.2.0]oct-4-ene-2-carboxylic acid methyl ester | 780782-13-0

• 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,6S,7R)-4-[1-(tert-Butyl-dimethyl-silanyloxy)-vinyl]-7-methoxy-8-oxo-1-aza-bicyclo[4.2.0]oct-4-ene-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,6S,7R)-4-[1-[tert-butyl(dimethyl)silyl]oxyethenyl]-7-methoxy-8-oxo-1-azabicyclo[4.2.0]oct-4-ene-2-carboxylate
• CAS: 780782-13-0
• 化学式: C₁₈H₂₉NO₅Si
• 分子量: 367.517
• InChiKey: NIYZFYZXJCNCNW-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-甲基马来酰亚胺 、 (2R,6S,7R)-4-[1-(tert-Butyl-dimethyl-silanyloxy)-vinyl]-7-methoxy-8-oxo-1-aza-bicyclo[4.2.0]oct-4-ene-2-carboxylic acid methyl ester 以 甲苯 为溶剂， 反应 12.0h， 以91%的产率得到methyl (1S,2R,6S,11R,14R,15S)-8-[tert-butyl(dimethyl)silyl]oxy-14-methoxy-4-methyl-3,5,13-trioxo-4,12-diazatetracyclo[7.6.0.02,6.012,15]pentadec-8-ene-11-carboxylate
  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 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 、 苯 为溶剂， 反应 2.5h， 生成 (2R,6S,7R)-4-[1-(tert-Butyl-dimethyl-silanyloxy)-vinyl]-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

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.