1,3-dibenzyl-1,2,3,4,5,6-hexahydropyrimidine-2,5-dione | 245679-89-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1,3-dibenzyl-1,2,3,4,5,6-hexahydropyrimidine-2,5-dione
• 英文别名: 1,3-Dibenzyltetrahydropyrimidine-2,5-dione；1,3-dibenzyl-1,3-diazinane-2,5-dione
• CAS: 245679-89-4
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: PTNJVDZPDWVGFX-UHFFFAOYSA-N

物化性质

• 沸点：
  508.8±50.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 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：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-dibenzyl-1,2,3,4,5,6-hexahydropyrimidine-2,5-dione 在 2,2,6,6-四甲基哌啶 、 正丁基锂 、 3 A molecular sieve 、 二甲基二环氧乙烷 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 7.17h， 生成 (4S)-1,3-dibenzyl-4-butyl-1,3-diazinane-2,5-dione
  参考文献：
  名称：

  Asymmetric Synthesis of 1,2,3,4,5,6-Hexahydro-5-hydroxypyrimidin-2-ones as Potential HIV-Protease Inhibitors

  摘要：

  DOI：

  10.1002/(sici)1522-2675(19990804)82:8<1195::aid-hlca1195>3.0.co;2-n
• 作为产物：
  描述：

  1,3-bis(benzylamino)propan-2-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 1,3-dibenzyl-1,2,3,4,5,6-hexahydropyrimidine-2,5-dione
  参考文献：
  名称：

  Asymmetric Synthesis of 1,2,3,4,5,6-Hexahydro-5-hydroxypyrimidin-2-ones as Potential HIV-Protease Inhibitors

  摘要：

  DOI：

  10.1002/(sici)1522-2675(19990804)82:8<1195::aid-hlca1195>3.0.co;2-n

文献信息

• Asymmetric Synthesis of 1,2,3,4,5,6-Hexahydro-5-hydroxypyrimidin-2-ones as Potential HIV-Protease Inhibitors
  作者：Dieter Enders、Lars Wortmann、Barbara Dücker、Gerhard Raabe

  DOI：10.1002/(sici)1522-2675(19990804)82:8<1195::aid-hlca1195>3.0.co;2-n

  日期：1999.8.4
• Asymmetric Synthesis of 4,6-Disubstituted 1,2,3,4,5,6-Hexahydro-5-hydroxypyrimidin-2-ones as Potential HIV-Protease-Inhibitors
  作者：Dieter Enders、Lars Wortmann

  DOI：10.3987/com-02-s(m)20

  日期：——

  The first asymmetric synthesis of potential HIV protease inhibitors of type III and IV is described. Key step of the synthesis is an auxiliary based stereoselective alkylation by means of the RAMP-/SAMP-hydrazone method starting from a readily available key building block. The synthesis is short and highly versatile in the choice of the substitution pattern as well as the absolute configuration of the products.
• A Highly Flexible Route to 1,2,3,4,5,6- Hexahydro-5-hydroxypyrimidin-2-ones as Potential HIV Protease Inhibitors
  作者：Dieter Enders、Lars Wortmann、Gerhard Raabe、Barbara Dücker

  DOI：10.3987/com-03-s(p)51

  日期：——

  The first asymmetric synthesis of potential HIV protease inhibitors of type II, III and IV is described. Key step of the synthesis is an auxiliary based stereoselective alkylation by means of the (R)-1-amino-2-methoxymethylpyrrolidine (RAMP)- / (S)-1-amino-2-methoxymethylpyrrolidine (SAMP)hydrazone method starting from a readily available key building block, pyrimidin-2,5-dione (6). The synthesis is short and highly versatile in the choice of the substitution pattern as well as the absolute configuration of the alkylated 1,2,3,4,5,6-Hexahydro-5-hydroxypyrimidin-2-ones.