(1'S,5S)-1-(benzyloxycarbonyl)-3-(1'-phenyleth-1'-yl)-5-(hydroxymethyl)imidazolidin-4-one | 138261-21-9

• 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,5S)-1-(benzyloxycarbonyl)-3-(1'-phenyleth-1'-yl)-5-(hydroxymethyl)imidazolidin-4-one
• 英文别名: benzyl (5S)-5-(hydroxymethyl)-4-oxo-3-[(1S)-1-phenylethyl]imidazolidine-1-carboxylate
• CAS: 138261-21-9
• 化学式: C₂₀H₂₂N₂O₄
• 分子量: 354.406
• InChiKey: FPBXZYZWVPTLNA-YJBOKZPZSA-N

物化性质

• 沸点：
  570.2±50.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3,5-tris((S)-α-methylbenzyl)hexahydrotriazine 在 sodium tetrahydroborate 、 氨 、 氧气 、 mercury(II) trifluoroacetate 、 碳酸氢钠 、 sodium bromide 作用下， 以 二氯甲烷 为溶剂， 反应 2.16h， 生成 (1'S,5S)-1-(benzyloxycarbonyl)-3-(1'-phenyleth-1'-yl)-5-(hydroxymethyl)imidazolidin-4-one
  参考文献：
  名称：

  A new route to the synthesis of amino acids through the mercury cyclization of chiral amidals

  摘要：

  By means of the mercury cyclization of the unsaturated amidals 3a-e, obtained from the reaction of 1,3,5-tris-[(S)-phenylethyl]hexahydrotriazine (1) and alpha,beta-unsaturated acyl chlorides, diastereomeric mixtures of imidazolidin-4-ones 5-8 and perihydropyrimidin-4-ones 9-10 have been synthesized and easily separated by flash chromatography. The subsequent hydrolysis under acid conditions of the separated heterocycles affords respectively D or L alpha- and beta-amino acids. The regiochemistry of the cyclization has been studied, depending on the substituents of the double bond. Furthermore the absolute configuration of the newly introduced stereogenic center has been attributed on the basis of the H-1 NMR spectra of the heterocycles.

  DOI：

  10.1021/jo00030a010

文献信息

• A new route to the synthesis of amino acids through the mercury cyclization of chiral amidals
  作者：Rosa Amoroso、Giuliana Cardillo、Claudia Tomasini、Paolo Tortoreto

  DOI：10.1021/jo00030a010

  日期：1992.2

  By means of the mercury cyclization of the unsaturated amidals 3a-e, obtained from the reaction of 1,3,5-tris-[(S)-phenylethyl]hexahydrotriazine (1) and alpha,beta-unsaturated acyl chlorides, diastereomeric mixtures of imidazolidin-4-ones 5-8 and perihydropyrimidin-4-ones 9-10 have been synthesized and easily separated by flash chromatography. The subsequent hydrolysis under acid conditions of the separated heterocycles affords respectively D or L alpha- and beta-amino acids. The regiochemistry of the cyclization has been studied, depending on the substituents of the double bond. Furthermore the absolute configuration of the newly introduced stereogenic center has been attributed on the basis of the H-1 NMR spectra of the heterocycles.