(1'S,6R)-1-(benzyloxycarbonyl)-3-(1'-phenyleth-1'-yl)-6-phenylperihydropyrimidin-4-one | 138261-27-5

• 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,6R)-1-(benzyloxycarbonyl)-3-(1'-phenyleth-1'-yl)-6-phenylperihydropyrimidin-4-one
• 英文别名: benzyl (6R)-4-oxo-6-phenyl-3-[(1S)-1-phenylethyl]-1,3-diazinane-1-carboxylate
• CAS: 138261-27-5
• 化学式: C₂₆H₂₆N₂O₃
• 分子量: 414.504
• InChiKey: UMOOMZGMPKILTN-GBXCKJPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  碘乙烷 、 (1'S,6R)-1-(benzyloxycarbonyl)-3-(1'-phenyleth-1'-yl)-6-phenylperihydropyrimidin-4-one 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到benzyl (5S,6R)-5-ethyl-4-oxo-6-phenyl-3-[(1S)-1-phenylethyl]-1,3-diazinane-1-carboxylate
  参考文献：
  名称：

  Highly Diastereoselective Alkylation of Perhydropyrimidin-4-ones Directed toward the Synthesis of .alpha.-Substituted .beta.-Amino Acids. 2.

  摘要：

  The alkylation of several enantiomerically pure perhydropyrimidin-4-ones at C-5 is described. For the methylation reaction, mixtures of 5,6-trans- and cis-disubstituted adducts were obtained with high diastereomeric ratios, whereas only the 5,6-trans-disubstituted products were obtained with larger alkylating agents. The dialkylation reaction at C-5 was also studied, and the 5,6-cis-trisubstituted product was preferentially formed. Acidic,hydrolysis of 5,6-trans-disubstituted perhydropyrimidin-4-ones furnished the corresponding beta-amino acid hydrochlorides in quantitative yield. On cyclization of the amino acids, 5,6-trans-disubstituted azetidin-2-ones were also synthesized.

  DOI：

  10.1021/jo00103a020
• 作为产物：
  描述：

  DL-3-氨基-3-苯基丙酸 在 sodium hydroxide 、 氯化亚砜 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 3.5h， 生成 (1'S,6R)-1-(benzyloxycarbonyl)-3-(1'-phenyleth-1'-yl)-6-phenylperihydropyrimidin-4-one
  参考文献：
  名称：

  Highly Diastereoselective Alkylation of Perhydropyrimidin-4-ones Directed toward the Synthesis of .alpha.-Substituted .beta.-Amino Acids. 2.

  摘要：

  The alkylation of several enantiomerically pure perhydropyrimidin-4-ones at C-5 is described. For the methylation reaction, mixtures of 5,6-trans- and cis-disubstituted adducts were obtained with high diastereomeric ratios, whereas only the 5,6-trans-disubstituted products were obtained with larger alkylating agents. The dialkylation reaction at C-5 was also studied, and the 5,6-cis-trisubstituted product was preferentially formed. Acidic,hydrolysis of 5,6-trans-disubstituted perhydropyrimidin-4-ones furnished the corresponding beta-amino acid hydrochlorides in quantitative yield. On cyclization of the amino acids, 5,6-trans-disubstituted azetidin-2-ones were also synthesized.

  DOI：

  10.1021/jo00103a020

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.