p-nitrobenzyl (6S,7S)-3-bromomethyl-7-(4-nitrophthalimido)-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate | 156662-52-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: p-nitrobenzyl (6S,7S)-3-bromomethyl-7-(4-nitrophthalimido)-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate
• CAS: 156662-52-1
• 化学式: C₂₃H₁₅BrN₄O₁₀
• 分子量: 587.297
• InChiKey: XBNDKYFWKHRKRZ-AEFFLSMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  179.5
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  p-nitrobenzyl (6S,7S)-3-bromomethyl-7-(4-nitrophthalimido)-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate 在 platinum on activated charcoal 氢气 、 碳酸氢钠 、 三乙胺 、 甲基肼 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， -50.0~25.0 ℃ 、392.24 kPa 条件下， 反应 4.5h， 生成 (6S,7S)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-cyclopentyloxyimino]-acetylamino}-8-oxo-3-([1,3,4]thiadiazol-2-ylsulfanylmethyl)-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  A convenient one pot asymmetric synthesis of cis-β-lactams: Key precursors for optically active 2-oxaisocephems

  摘要：

  Asymmetric annelation of the disilylated imine 3 generated in situ from D-threonine 2 with acid chlorides 4 and triethylamine followed by esterification provided cis-beta-lactams 5 and 6 in excellent yields with high diastereoselectivity under mild conditions. And conversion of compounds 5 into 15, derivatives of 2-oxaisocephems having a thio-substituted methyl group at the 3-position and a 2-aminothiazol-4-yl moiety at the 7-position, is described. Biological activities of the new compounds are presented. In particular, 15b showed potent antibacterial activity against Methicillin-resistant Staphylococcus aureus (MRSA) and Enterococcus faecalis which cause a serious clinical problem in antibacterial chemotherapy.

  DOI：

  10.1016/s0957-4166(00)86216-3
• 作为产物：
  描述：

  (2R,3S)-3-Hydroxy-2-[(2S,3S)-2-methanesulfonyloxymethyl-3-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-1-yl]-butyric acid 4-nitro-benzyl ester 在 chromium(VI) oxide 、 硫酸 、 溴 、 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 反应 3.67h， 生成 p-nitrobenzyl (6S,7S)-3-bromomethyl-7-(4-nitrophthalimido)-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate
  参考文献：
  名称：

  A convenient one pot asymmetric synthesis of cis-β-lactams: Key precursors for optically active 2-oxaisocephems

  摘要：

  Asymmetric annelation of the disilylated imine 3 generated in situ from D-threonine 2 with acid chlorides 4 and triethylamine followed by esterification provided cis-beta-lactams 5 and 6 in excellent yields with high diastereoselectivity under mild conditions. And conversion of compounds 5 into 15, derivatives of 2-oxaisocephems having a thio-substituted methyl group at the 3-position and a 2-aminothiazol-4-yl moiety at the 7-position, is described. Biological activities of the new compounds are presented. In particular, 15b showed potent antibacterial activity against Methicillin-resistant Staphylococcus aureus (MRSA) and Enterococcus faecalis which cause a serious clinical problem in antibacterial chemotherapy.

  DOI：

  10.1016/s0957-4166(00)86216-3