(5R,7S,8R,8aS)-2-Benzyl-7-hydroxy-5-hydroxymethyl-8-methyl-hexahydro-imidazo[1,5-a]pyridin-3-one | 893403-35-5

• 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: (5R,7S,8R,8aS)-2-Benzyl-7-hydroxy-5-hydroxymethyl-8-methyl-hexahydro-imidazo[1,5-a]pyridin-3-one
• 英文别名: (5R,7S,8R,8aS)-2-benzyl-7-hydroxy-5-(hydroxymethyl)-8-methyl-1,5,6,7,8,8a-hexahydroimidazo[1,5-a]pyridin-3-one
• CAS: 893403-35-5
• 化学式: C₁₆H₂₂N₂O₃
• 分子量: 290.362
• InChiKey: NJOVZOMOZVGRIR-NGFQHRJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  64
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R,7S,8R,8aS)-2-Benzyl-7-hydroxy-5-hydroxymethyl-8-methyl-hexahydro-imidazo[1,5-a]pyridin-3-one 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 正丁基锂 、 碘苯二乙酸 、 trimethoxythioether 作用下， 以 四氢呋喃 、 氘代氯仿 为溶剂， 反应 0.58h， 生成
  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
• 作为产物：
  描述：

  (2R)-tert-butoxycarbonylaminohex-(4E)-enoic acid 在 palladium on activated charcoal disodium hydrogenphosphate 、 lithium aluminium tetrahydride 、 氢气 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 、 乙酰氯 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， -78.0~200.0 ℃ 、101.33 kPa 条件下， 反应 10.0h， 生成 (5R,7S,8R,8aS)-2-Benzyl-7-hydroxy-5-hydroxymethyl-8-methyl-hexahydro-imidazo[1,5-a]pyridin-3-one
  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

文献信息

• Syntheses of the cylindrospermopsin alkaloids
  作者：Ryan E. Looper、Maria T.C. Runnegar、Robert M. Williams

  DOI：10.1016/j.tet.2006.02.044

  日期：2006.5

  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.