(2R*,2'S*,4S*,4'R*)-4,4'-diethyl-2,2'-perhydrobipyrimidine | 220064-12-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2R*,2'S*,4S*,4'R*)-4,4'-diethyl-2,2'-perhydrobipyrimidine
• 英文别名: (2R,4S)-4-ethyl-2-[(2S,4R)-4-ethyl-1,3-diazinan-2-yl]-1,3-diazinane
• CAS: 220064-12-0
• 化学式: C₁₂H₂₆N₄
• 分子量: 226.365
• InChiKey: HLSGYNMTAKUEPA-IWDIQUIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  48.1
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (2R*,2'S*,4S*,4'R*)-4,4'-diethyl-2,2'-perhydrobipyrimidine 以 甲醇 、 水 为溶剂， 反应 1.0h， 以37%的产率得到(3S*,4aS*,4bR*,6R*)-4a,4b-cis-3,6-diethyl-4,5,8a,9a-tetraazafluorene
  参考文献：
  名称：

  Chemoselectivity and stereoselectivity in the condensation reactions of 4,4′-diethyl-2,2′-perhydrobipyrimidine

  摘要：

  Rac 1,3-pentanediamine reacts with glyoxal to give a 1:1 mixture of diastereomers from which can be isolated (2R*,2'S*,4S*,4'R*)-4,4'-diethylperhydro-2,2'-bipyrimidine. Subsequent treatment with HCHO, MeCHO, EtCHO, and i-PrCHO gives cis and to a lesser extent trans fused 1:1 condensation products, which are 4a,4b-cis-3,6-diethylperhydro-4,5,8a,9a-tetraazafluorene and 4a,4b-trans-1,6-diethylperhydro-4,5,8a,9a-tetraazafluorene derivatives, or tetracyclic cis fused 1:2 condensation products, 8b,8c-cis-3,5-diethylperhydro-3a,4a,7a,8a-tetraazacyclopentano[def]- fluorenes, respectively, depending on conditions. 2-Phenylacetaldehyde reacts to give cis and trans 2-benzyl-4-ethylhexahydropyrimidine. The effects of aldehyde and solvent upon the outcome are discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00961-2
• 作为产物：
  描述：

  草酸醛 、 1,3-二氨基戊烷 以 水 为溶剂， 反应 3.5h， 以12%的产率得到(2R*,2'S*,4S*,4'R*)-4,4'-diethyl-2,2'-perhydrobipyrimidine
  参考文献：
  名称：

  Chemoselectivity and stereoselectivity in the condensation reactions of 4,4′-diethyl-2,2′-perhydrobipyrimidine

  摘要：

  Rac 1,3-pentanediamine reacts with glyoxal to give a 1:1 mixture of diastereomers from which can be isolated (2R*,2'S*,4S*,4'R*)-4,4'-diethylperhydro-2,2'-bipyrimidine. Subsequent treatment with HCHO, MeCHO, EtCHO, and i-PrCHO gives cis and to a lesser extent trans fused 1:1 condensation products, which are 4a,4b-cis-3,6-diethylperhydro-4,5,8a,9a-tetraazafluorene and 4a,4b-trans-1,6-diethylperhydro-4,5,8a,9a-tetraazafluorene derivatives, or tetracyclic cis fused 1:2 condensation products, 8b,8c-cis-3,5-diethylperhydro-3a,4a,7a,8a-tetraazacyclopentano[def]- fluorenes, respectively, depending on conditions. 2-Phenylacetaldehyde reacts to give cis and trans 2-benzyl-4-ethylhexahydropyrimidine. The effects of aldehyde and solvent upon the outcome are discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00961-2