tert-butyl 1'-(4-((S)-5-(acetamidomethyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl)-2-oxa-3-azaspiro[bicyclo[2.2.1]heptane-7,4'-piperidine]-3-carboxylate | 1380494-58-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl 1'-(4-((S)-5-(acetamidomethyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl)-2-oxa-3-azaspiro[bicyclo[2.2.1]heptane-7,4'-piperidine]-3-carboxylate
• 英文别名: tert-butyl 1'-[4-[(5S)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]spiro[2-oxa-3-azabicyclo[2.2.1]heptane-7,4'-piperidine]-3-carboxylate
• CAS: 1380494-58-5
• 化学式: C₂₆H₃₅FN₄O₆
• 分子量: 518.586
• InChiKey: CLLQCZDASJZQQE-XTWGIRIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl 1'-(4-((S)-5-(acetamidomethyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl)-2-oxa-3-azaspiro[bicyclo[2.2.1]heptane-7,4'-piperidine]-3-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到N-(((5S)-3-(3-fluoro-4-(2-oxa-3-azaspiro[bicyclo[2.2.1]heptane-7,4'-piperidin]-1'-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide
  参考文献：
  名称：

  Syntheses and biological studies of novel spiropiperazinyl oxazolidinone antibacterial agents using a spirocyclic diene derived acylnitroso Diels−Alder reaction

  摘要：

  Several novel oxazolidinone antibiotics with a spiropiperazinyl substituent at the 4'-position of the phenyl ring were synthesized through nitroso Diels-Alder chemistry and the in vitro antibacterial activities were evaluated against various Gram-positive bacteria (Bacillus subtilis, Staphylococcus aureus, Enterococcus faecalis), Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa) and mycobacteria (Mycobacterium vaccae, Mycobacterium tuberculosis). Analogs (8a and 12) were active against selected drug resistant microbes, like methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE) and had no mammalian toxicity in a Hep-2 cellular assay (CC50 > 100 mu M). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.026
• 作为产物：
  描述：

  N-羟基氨基甲酸叔丁酯 在 吡啶 、 sodium periodate 、 正丁基锂 、 sodium azide 、 palladium 10% on activated carbon 、 20% palladium hydroxide-activated charcoal 、 氢气 、 碳酸氢钠 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， -78.0~80.0 ℃ 、344.75 kPa 条件下， 反应 73.25h， 生成 tert-butyl 1'-(4-((S)-5-(acetamidomethyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl)-2-oxa-3-azaspiro[bicyclo[2.2.1]heptane-7,4'-piperidine]-3-carboxylate
  参考文献：
  名称：

  Syntheses and biological studies of novel spiropiperazinyl oxazolidinone antibacterial agents using a spirocyclic diene derived acylnitroso Diels−Alder reaction

  摘要：

  Several novel oxazolidinone antibiotics with a spiropiperazinyl substituent at the 4'-position of the phenyl ring were synthesized through nitroso Diels-Alder chemistry and the in vitro antibacterial activities were evaluated against various Gram-positive bacteria (Bacillus subtilis, Staphylococcus aureus, Enterococcus faecalis), Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa) and mycobacteria (Mycobacterium vaccae, Mycobacterium tuberculosis). Analogs (8a and 12) were active against selected drug resistant microbes, like methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE) and had no mammalian toxicity in a Hep-2 cellular assay (CC50 > 100 mu M). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.026