N-p-methoxybenzyl-3-methylisoxazolidin-5-one | 394220-59-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-p-methoxybenzyl-3-methylisoxazolidin-5-one
• 英文别名: (3R)-2-[(4-methoxyphenyl)methyl]-3-methyl-1,2-oxazolidin-5-one
• CAS: 394220-59-8
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: GWGUDTZTUJNYCE-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-p-methoxybenzyl-3-methylisoxazolidin-5-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以86%的产率得到(R)-3-氨基丁酸
  参考文献：
  名称：

  Enantioselective Conjugate Addition of Hydroxylamines to Pyrazolidinone Acrylamides

  摘要：

  [GRAPHICS]Chiral relay templates provide amplification of selectivity in conjugate addition reactions. Reversal of stereochemistry of the product isoxazolidinones has also been demonstrated by a simple change of the Lewis acid.

  DOI：

  10.1021/ol016807t
• 作为产物：
  描述：

  N-(4-甲氧基苄基)羟胺 、 1-(1-naphthylmethyl)-2-[(E)-2-butenoyl]-5,5-dimethyl-pyrazolidin-3-one 在 magnesium(II) perchlorate 、 (3aS,3a'S,8aR,8a'R)-2,2'-(cyclopropane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole) 作用下， 反应 5.0h， 生成 N-p-methoxybenzyl-3-methylisoxazolidin-5-one 、 N-p-methoxybenzyl-3-methylisoxazolidin-5-one
  参考文献：
  名称：

  Enantioselective Conjugate Addition of Hydroxylamines to Pyrazolidinone Acrylamides

  摘要：

  [GRAPHICS]Chiral relay templates provide amplification of selectivity in conjugate addition reactions. Reversal of stereochemistry of the product isoxazolidinones has also been demonstrated by a simple change of the Lewis acid.

  DOI：

  10.1021/ol016807t

文献信息

• <i>N</i>-Benzylhydroxylamine Addition to β-Aryl Enoates. Enantioselective Synthesis of β-Aryl-β-amino Acid Precursors
  作者：Mukund P. Sibi、Mei Liu

  DOI：10.1021/ol006500e

  日期：2000.10.1

  [GRAPHICS]Chiral Lewis acid catalyzed N-benzylhydroxylamine addition to pyrrolidinone-derived enoates afforded beta-aryl-beta-amino acid derivatives in high enantiomeric purity with moderate to very good chemical efficiency.
• Enantioselective Conjugate Addition of Hydroxylamines to Pyrazolidinone Acrylamides
  作者：Mukund P. Sibi、Mei Liu

  DOI：10.1021/ol016807t

  日期：2001.12.1

  [GRAPHICS]Chiral relay templates provide amplification of selectivity in conjugate addition reactions. Reversal of stereochemistry of the product isoxazolidinones has also been demonstrated by a simple change of the Lewis acid.