6-((2aS,3R,4S,5aS,7R)-4-Hydroxy-3-methyl-2,2a,3,4,5,5a,6,7-octahydro-1H-1,8,8b-triaza-acenaphthylen-7-ylmethyl)-1H-pyrimidine-2,4-dione | 1644631-81-1

• 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: 6-((2aS,3R,4S,5aS,7R)-4-Hydroxy-3-methyl-2,2a,3,4,5,5a,6,7-octahydro-1H-1,8,8b-triaza-acenaphthylen-7-ylmethyl)-1H-pyrimidine-2,4-dione
• 英文别名: 7-Deoxy-desulfo-cylindrospermopsin；6-[[(4S,5R,6S,8S,10R)-6-hydroxy-5-methyl-2,11,12-triazatricyclo[6.3.1.04,12]dodec-1-en-10-yl]methyl]-1H-pyrimidine-2,4-dione
• CAS: 1644631-81-1
• 化学式: C₁₅H₂₁N₅O₃
• 分子量: 319.363
• InChiKey: HKUZFYRVEQYWCO-GATYQTQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  106
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,6-bis(benzyloxy)pyrimidine-4-carbaldehyde 在 sodium tetrahydroborate 、 乙酸酐 、 cesium fluoride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 6-((2aS,3R,4S,5aS,7R)-4-Hydroxy-3-methyl-2,2a,3,4,5,5a,6,7-octahydro-1H-1,8,8b-triaza-acenaphthylen-7-ylmethyl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Syntheses of the cylindrospermopsin alkaloids

  摘要：

  An intramolecular 1,3-dipolar cycloaddition has efficiently constructed the A-ring portions of the cylindrospermopsin alkaloids. A nitro-aldol addition of an elaborated nitroalkane to a pyrimidine aldehyde followed by an intramolecular reductive guanidinylation has enabled the syntheses of all three alkaloids in this family in 18-19 steps. We report the first asymmetric synthesis of cylindrospermopsin, unambiguously assigning its absolute configuration. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.044