N-tert-butoxycarbonyl-3-(N-tert-butoxycarbonyl)aminomethyl-3-methyl-4-oxopyrrolidine | 1356857-64-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-tert-butoxycarbonyl-3-(N-tert-butoxycarbonyl)aminomethyl-3-methyl-4-oxopyrrolidine
• 英文别名: Tert-butyl 3-methyl-3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-4-oxopyrrolidine-1-carboxylate
• CAS: 1356857-64-1
• 化学式: C₁₆H₂₈N₂O₅
• 分子量: 328.409
• InChiKey: BKDMYMQRYHENQI-UHFFFAOYSA-N

物化性质

• 沸点：
  437.4±30.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-3-(N-tert-butoxycarbonyl)aminomethyl-3-methyl-4-oxopyrrolidine 在 吡啶 、 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以93.1%的产率得到tert-butyl 3-(tert-butoxycarbonyl)aminomethyl-3-methyl-4-(hydroxyimino) pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis and antibacterial activity of naphthyridone derivatives containing mono/difluoro-methyloxime pyrrolidine scaffolds

  摘要：

  A series of novel naphthyridone derivatives containing mono/difluoro-methyloxime pyrrolidine scaffolds were designed and synthesized. These derivatives were initially evaluated for their in vitro antibacterial activity and compounds 13a1, b1 were chosen for further evaluation their in vivo activity against systemic infections in mice. The results indicate that all of the target compounds have considerable in vitro antibacterial activity. In the in vivo experiments, 13b1 was found to be more effective than the parent drug gemifloxacin against the tested five strains, and especially its activity (ED50:21.27 mg/kg) is 5.2-6.1 times more potent than gemifloxacin and ciprofloxacin against clinically important Gram-negative pathogen Pseudomonas aeruginosa. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.048
• 作为产物：
  描述：

  1-Boc-3-氰基-4-吡咯烷酮 在 5%-palladium/activated carbon 、 氢气 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、517.12 kPa 条件下， 反应 8.0h， 生成 N-tert-butoxycarbonyl-3-(N-tert-butoxycarbonyl)aminomethyl-3-methyl-4-oxopyrrolidine
  参考文献：
  名称：

  A Convenient Way to Prepare the Key Intermediate 3-Aminomethyl-3-methyl-4-(metho-xyimino)pyrrolidine Dihydrochloride of DW286, a New Naphthyridone Antibacterial

  摘要：

  我们在此报告一种简便的方法，通过 4 个步骤制备新型氟萘啶酮类抗菌剂 DW286 的关键中间体 3-氨甲基-3-甲基-4-（甲氧基亚氨基）吡咯烷二盐酸盐，总收率为 56%。在这一过程中，关键是使用 5 % Pd/C 作为催化氢化物，成功地完成了氰酮 (5) 氰基的选择性还原。

  DOI：

  10.14233/ajchem.2013.13280

文献信息

• Synthesis, antimycobacterial and antibacterial activity of l-[(1R,2S)-2-fluorocyclopropyl]naphthyridone derivatives containing an oxime-functionalized pyrrolidine moiety
  作者：Ju Huang、Hongtao Liu、Mingliang Liu、Rui Zhang、Linhu Li、Bin Wang、Minghua Wang、Chunlan Wang、Yu Lu

  DOI：10.1016/j.bmcl.2015.10.027

  日期：2015.11

  A series of novel 1-[(1R,2S)-2-fluorocyclopropyl]naphthyridone derivatives 21-24 containing an oxime-functionalized pyrrolidine moiety were designed, synthesized and evaluated for their biological activity. Our results reveal that compounds 21a, 21e and 21j show considerable activity against MTB H37Rv ATCC 27294 (MICs: <0.25 mu g/mL) and MDR-MTB 6133 (MICs: 0.03-0.054 lg/mL). The target compounds 21-24 are generally poor against the Gram-negative strains, but 21a-j and 22a-c have potent potency (MICs: <0.008-32 mu g/mL) against all of the tested Gram-positive strains including MRSA and MRSE with a few exceptions, and the most active compounds 21d, 21e and 22a-c (MICs: <0.008-32 mu g/mL) were found to be comparable to or better than moxifloxacin, and 2->250 times more potent than ciprofloxacin and levofloxacin. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and antibacterial activity of naphthyridone derivatives containing mono/difluoro-methyloxime pyrrolidine scaffolds
  作者：Kai Lv、Ming-Liang Liu、Lian-Shun Feng、Lan-Ying Sun、Ye-Xin Sun、Zeng-Quan Wei、Hui-Quan Guo

  DOI：10.1016/j.ejmech.2011.10.048

  日期：2012.1

  A series of novel naphthyridone derivatives containing mono/difluoro-methyloxime pyrrolidine scaffolds were designed and synthesized. These derivatives were initially evaluated for their in vitro antibacterial activity and compounds 13a1, b1 were chosen for further evaluation their in vivo activity against systemic infections in mice. The results indicate that all of the target compounds have considerable in vitro antibacterial activity. In the in vivo experiments, 13b1 was found to be more effective than the parent drug gemifloxacin against the tested five strains, and especially its activity (ED50:21.27 mg/kg) is 5.2-6.1 times more potent than gemifloxacin and ciprofloxacin against clinically important Gram-negative pathogen Pseudomonas aeruginosa. (C) 2011 Elsevier Masson SAS. All rights reserved.
• A Convenient Way to Prepare the Key Intermediate 3-Aminomethyl-3-methyl-4-(metho-xyimino)pyrrolidine Dihydrochloride of DW286, a New Naphthyridone Antibacterial
  作者：Lian-Shun Feng、Ming-Liang Liu、Kai Lv、Yun Chai、Shuo Wang、Jue Cao、Hui-Yuan Guo

  DOI：10.14233/ajchem.2013.13280

  日期：——

  We report herein a convenient way to prepare the key intermediate 3-aminomethyl-3-methyl-4-(methoxyimino)pyrrolidine dihydrochloride of DW286, a new fluoronaphthyridone antibacterial agent, via a 4-step sequence in an overall yield of 56 %. In this procedure, it was crucial that selective reduction of the cyano group of the cyano ketone (5) was done successfully using 5 % Pd/C as the catalytic hydrogenation.

  我们在此报告一种简便的方法，通过 4 个步骤制备新型氟萘啶酮类抗菌剂 DW286 的关键中间体 3-氨甲基-3-甲基-4-（甲氧基亚氨基）吡咯烷二盐酸盐，总收率为 56%。在这一过程中，关键是使用 5 % Pd/C 作为催化氢化物，成功地完成了氰酮 (5) 氰基的选择性还原。