(1'S,6S)-1-benzyloxycarbonyl-3-(1'-phenyleth-1'-yl)-6-methylperihydropyrimidin-4-one | 141632-87-3

• 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: (1'S,6S)-1-benzyloxycarbonyl-3-(1'-phenyleth-1'-yl)-6-methylperihydropyrimidin-4-one
• 英文别名: benzyl (6S)-6-methyl-4-oxo-3-[(1S)-1-phenylethyl]-1,3-diazinane-1-carboxylate
• CAS: 141632-87-3
• 化学式: C₂₁H₂₄N₂O₃
• 分子量: 352.433
• InChiKey: KDLAUVJJRHPDSG-IRXDYDNUSA-N

物化性质

• 沸点：
  531.7±50.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.85
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1'S,6S)-1-benzyloxycarbonyl-3-(1'-phenyleth-1'-yl)-6-methylperihydropyrimidin-4-one 在 盐酸 作用下， 反应 12.0h， 以65%的产率得到(S)-3-氨基丁酸
  参考文献：
  名称：

  Amoroso, Rosa; Cardillo, Giuliana; Tomasini, Claudia, Heterocycles, 1992, vol. 34, # 2, p. 349 - 355

  摘要：

  DOI：
• 作为产物：
  描述：

  N-aminomethyl-N-(S)-phenylethylamide 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 (1'S,6S)-1-benzyloxycarbonyl-3-(1'-phenyleth-1'-yl)-6-methylperihydropyrimidin-4-one
  参考文献：
  名称：

  Amoroso, Rosa; Cardillo, Giuliana; Tomasini, Claudia, Heterocycles, 1992, vol. 34, # 2, p. 349 - 355

  摘要：

  DOI：

文献信息

• Highly diastereoselective alkylation of 6-methylperihydropyrimidin-4-ones directed towards the synthesis of α-substituted β-amino acids
  作者：Rosa Amoroso、Giuliana Cardillo、Claudia Tomasini

  DOI：10.1016/s0040-4039(00)79067-8

  日期：1992.5

  The highly diastereoselective alkylation of 6-methylperihydropyrimidin-4-ones 1 and 2 has been reported. The corresponding lithium enolates have been alkylated under a variety of conditions with good trans selectivity and all the reaction products have been easily separated and characterised.

  已经报道了6-甲基全氢嘧啶-4-酮1和2的高度非对映选择性烷基化。相应的烯醇锂已经在多种条件下以良好的反选择性被烷基化，并且所有反应产物都易于分离和表征。
• Metal-assisted aldol condensation of chiral 6-methyl perihydropyrimidin-4-ones
  作者：Rosa Amoroso、Giuliana Cardillo、Giovanna Mobbili、Claudia Tomasini

  DOI：10.1016/s0957-4166(00)80074-9

  日期：1993.10

  The synthesis of 6-methyl perihydropyrimidin-4-ones (1'S,6R)-3a and (1'S,6S)-3b is reported starting from rac-3-aminobutanoic acid. The aldol condensation of various metal enolates of 3a and 3b with benzaldehyde and acetaldehyde is reported. All reactions afford complete facial diastereoselectivity and good simple diastereoselectivity, depending on the nature of the enolate and of the aldehyde. The reaction yields are generally good and the aldols have been characterized by means of H-1 NMR spectroscopy and NOEDIFF experiments.
• Formation of Aziridine-2-amides through 5-Halo-6-methylperhydropyrimidin-4-ones. A Route to Enantiopure <scp>l</scp>- and <scp>d</scp>-Threonine and <i>allo</i>-Threonine
  作者：Giuliana Cardillo、Luca Gentilucci、Alessandra Tolomelli、Claudia Tomasini

  DOI：10.1021/jo971388s

  日期：1998.5.1