N-tert-butoxycarbonyl-3-cyano-4-(ethoxymino)pyrrolidine | 1339961-05-5

• 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-cyano-4-(ethoxymino)pyrrolidine
• CAS: 1339961-05-5
• 化学式: C₁₂H₁₉N₃O₃
• 分子量: 253.301
• InChiKey: XEHNSIYNWHKPGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  74.92
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-3-cyano-4-(ethoxymino)pyrrolidine 在 sodium hypobromide 、 碘代三甲硅烷 、 双氧水 、 sodium hydride 、 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 二甲基亚砜 、 乙腈 为溶剂， 反应 11.17h， 生成 1-(pyridin-3-yl)-6-fluoro-7-[1-methyl-8-(ethoxyimino)-1,6-diazaspiro[3.4]oct-6-yl]-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of naphthyridone derivatives containing 8-alkoxyimino-1,6-dizaspiro[3.4]octane scaffolds

  摘要：

  The synthesis of naphthyridone derivatives containing 8-alkoxyimino-1.6-dizaspiro[3.4]octane scaffolds, the position isomers of the side chain at the C-7 position of Zabofloxacin, has been achieved in eight steps from tert-butyl 3-cyano-4-oxopyrrolidine-1-carboxylate. The possible reaction mechanisms were also proposed. The key spirocyclic carbamate esters, which could be prepared using a modified Hofmann rearrangement strategy, were condensed with naphthyridone nuclei, and the resulting condensates were easily cleaved by TMSI and subsequently cyclized in the presence of K(2)CO(3). Moreover, additional N-methylation derivatives were also obtained using the synthetic sequence. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.089
• 作为产物：
  描述：

  乙氧基胺盐酸盐 、 1-Boc-3-氰基-4-吡咯烷酮 在 吡啶 作用下， 以 甲醇 为溶剂， 以87%的产率得到N-tert-butoxycarbonyl-3-cyano-4-(ethoxymino)pyrrolidine
  参考文献：
  名称：

  Synthesis of naphthyridone derivatives containing 8-alkoxyimino-1,6-dizaspiro[3.4]octane scaffolds

  摘要：

  The synthesis of naphthyridone derivatives containing 8-alkoxyimino-1.6-dizaspiro[3.4]octane scaffolds, the position isomers of the side chain at the C-7 position of Zabofloxacin, has been achieved in eight steps from tert-butyl 3-cyano-4-oxopyrrolidine-1-carboxylate. The possible reaction mechanisms were also proposed. The key spirocyclic carbamate esters, which could be prepared using a modified Hofmann rearrangement strategy, were condensed with naphthyridone nuclei, and the resulting condensates were easily cleaved by TMSI and subsequently cyclized in the presence of K(2)CO(3). Moreover, additional N-methylation derivatives were also obtained using the synthetic sequence. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.089