benzyl (5R,6S)-6-ethyl-5-methyl-4-oxo-3-[(1S)-1-phenylethyl]-1,3-diazinane-1-carboxylate | 159391-70-5

• 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: benzyl (5R,6S)-6-ethyl-5-methyl-4-oxo-3-[(1S)-1-phenylethyl]-1,3-diazinane-1-carboxylate
• CAS: 159391-70-5
• 化学式: C₂₃H₂₈N₂O₃
• 分子量: 380.487
• InChiKey: KQTQHNHIXFUMCM-LQWHRVPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 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 、 benzyl (5R,6S)-6-ethyl-5-methyl-4-oxo-3-[(1S)-1-phenylethyl]-1,3-diazinane-1-carboxylate 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 、 benzyl (5R,6S)-5,6-diethyl-5-methyl-4-oxo-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：

  3-氨基戊酸 在 sodium hydroxide 、 氯化亚砜 、 对甲苯磺酸 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 6.5h， 生成 benzyl (5R,6S)-6-ethyl-5-methyl-4-oxo-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

文献信息

• Highly Diastereoselective Alkylation of Perhydropyrimidin-4-ones Directed toward the Synthesis of .alpha.-Substituted .beta.-Amino Acids. 2.
  作者：Ilaria Braschi、Giuliana Cardillo、Claudia Tomasini、Roberto Venezia

  DOI：10.1021/jo00103a020

  日期：1994.12

  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.