4-(α-methylbenzylamino)-2-methyl-5-phenylisoxazolidin-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 4-(α-methylbenzylamino)-2-methyl-5-phenylisoxazolidin-3-one
• 英文别名: (4R,5R)-2-methyl-5-phenyl-4-(1-phenylethylamino)-1,2-oxazolidin-3-one
• 化学式: C₁₈H₂₀N₂O₂
• 分子量: 296.369
• InChiKey: JUHVDPUKFYKAKF-SYFTWWQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  、 N-甲基羟胺盐酸盐 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 0.08h， 生成 4-(α-methylbenzylamino)-2-methyl-5-phenylisoxazolidin-3-one 、 4-(α-methylbenzylamino)-2-methyl-5-phenylisoxazolidin-3-one
  参考文献：
  名称：

  Regioselective ring opening of β-phenylglycidate and aziridine-2-carboxylates with N-alkylhydroxylamines: synthesis of isoxazolidinones

  摘要：

  A simple and efficient method for the synthesis of 4-hydroxy or 4-alkylamino isoxazolidin-3-ones and 4-hydroxy isoxazolidin-5-ones is described: The synthesis involved the ring opening of ethyl beta-arylglycidates or ethyl N-alkylaziridine-2-carboxylates by free N-alkylhydroxylamines or hydroxylamine anions, followed by cyclization to give the title isoxazolidinones in moderate to good yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.052

文献信息

• Regioselective ring opening of β-phenylglycidate and aziridine-2-carboxylates with N-alkylhydroxylamines: synthesis of isoxazolidinones
  作者：Mohamed Ali Tabarki、Rafâa Besbes

  DOI：10.1016/j.tet.2013.12.052

  日期：2014.2

  A simple and efficient method for the synthesis of 4-hydroxy or 4-alkylamino isoxazolidin-3-ones and 4-hydroxy isoxazolidin-5-ones is described: The synthesis involved the ring opening of ethyl beta-arylglycidates or ethyl N-alkylaziridine-2-carboxylates by free N-alkylhydroxylamines or hydroxylamine anions, followed by cyclization to give the title isoxazolidinones in moderate to good yields. (C) 2013 Elsevier Ltd. All rights reserved.