(4R)-N-benzyloxycarbonyl-4-phenyl-1,3-oxazinan-6-one | 922705-36-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4R)-N-benzyloxycarbonyl-4-phenyl-1,3-oxazinan-6-one
• 英文别名: benzyl (4R)-6-oxo-4-phenyl-1,3-oxazinane-3-carboxylate
• CAS: 922705-36-0
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: UPWRJEIYZWTDAA-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R)-N-benzyloxycarbonyl-4-phenyl-1,3-oxazinan-6-one 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以89%的产率得到(3R)-N-benzyloxycarbonyl-3-amino-3-phenylpropanoic acid
  参考文献：
  名称：

  Diastereoselective Synthesis of α-Methyl and α-Hydroxy-β-Amino Acids via 4-Substituted-1,3-Oxazinan-6-ones

  摘要：

  1,3-Oxazinan-6-ones have been utilized in a series of enolate reactions to produce 5-hydroxy and 5-alkyl-4-substituted-1,3-oxazinan-6-ones with excellent trans diastereoselectivity. Highlighting the versatility of the oxazinanone, a number of transformations were performed to produce a variety of protected N-H and N-methyl alpha-hydroxy- and alpha-methyl-beta-amino acids.

  DOI：

  10.1021/jo0700326
• 作为产物：
  描述：

  聚合甲醛 、 (3R)-N-benzyloxycarbonyl-3-amino-3-phenylpropanoic acid 在 4 A molecular sieve 、 camphor-10-sulfonic acid 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以55%的产率得到(4R)-N-benzyloxycarbonyl-4-phenyl-1,3-oxazinan-6-one
  参考文献：
  名称：

  Diastereoselective Synthesis of α-Methyl and α-Hydroxy-β-Amino Acids via 4-Substituted-1,3-Oxazinan-6-ones

  摘要：

  1,3-Oxazinan-6-ones have been utilized in a series of enolate reactions to produce 5-hydroxy and 5-alkyl-4-substituted-1,3-oxazinan-6-ones with excellent trans diastereoselectivity. Highlighting the versatility of the oxazinanone, a number of transformations were performed to produce a variety of protected N-H and N-methyl alpha-hydroxy- and alpha-methyl-beta-amino acids.

  DOI：

  10.1021/jo0700326

文献信息

• Diastereoselective Synthesis of α-Methyl and α-Hydroxy-β-Amino Acids via 4-Substituted-1,3-Oxazinan-6-ones
  作者：Brad E. Sleebs、Andrew B. Hughes

  DOI：10.1021/jo0700326

  日期：2007.4.1

  1,3-Oxazinan-6-ones have been utilized in a series of enolate reactions to produce 5-hydroxy and 5-alkyl-4-substituted-1,3-oxazinan-6-ones with excellent trans diastereoselectivity. Highlighting the versatility of the oxazinanone, a number of transformations were performed to produce a variety of protected N-H and N-methyl alpha-hydroxy- and alpha-methyl-beta-amino acids.