8-benzyl-2-exo-hydroxy-8-azabicyclo<3.2.1>octane-6-exo-carbonitrile | 141557-06-4

• 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: 8-benzyl-2-exo-hydroxy-8-azabicyclo<3.2.1>octane-6-exo-carbonitrile
• 英文别名: 8-benzyl-2-exo-hydroxy-8-azabicyclo[3.2.1]octane-6-exo-carbonitrile；(1R,2S,5R,6S)-8-benzyl-2-hydroxy-8-azabicyclo[3.2.1]octane-6-carbonitrile
• CAS: 141557-06-4；141611-19-0
• 化学式: C₁₅H₁₈N₂O
• 分子量: 242.321
• InChiKey: XVJZMHJFKGAQGC-TUVASFSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-benzyl-2-exo-hydroxy-8-azabicyclo<3.2.1>octane-6-exo-carbonitrile 在 碘 、 magnesium 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 28.0h， 生成 1-<8-benzyl-2-exo--8-azabicyclo<3.2.1>oct-6-exo-yl>ethanone
  参考文献：
  名称：

  Preliminary Study of the Total Synthesis of Bao Gong Teng A Analogs Using 8-Benzyl-2-oxo-8-azabicyclo[3.2.1]oct-3-ene-6-endo/exo- and 7-endo/exo-carbonitrile

  摘要：

  DOI：

  10.3987/com-98-8447
• 作为产物：
  描述：

  1-benzyl-3-hydroxypyridinium bromide 在 钯 sodium tetrahydroborate 、 氢气 、 三乙胺 、 对苯二酚 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 42.0h， 生成 8-benzyl-2-exo-hydroxy-8-azabicyclo<3.2.1>octane-6-exo-carbonitrile
  参考文献：
  名称：

  Total synthesis of Bao Gong Teng A, a natural antiglaucoma compound

  摘要：

  The total synthesis of Bao Gong Tong A (1), a novel natural product which shows antiglaucoma properties is described. The key step involves the highly regioselective and somewhat stereoselective 1,3-dipolar cycloaddition of acrylonitrile to N-benzyl-3-hydroxypyridinium bromide 2 to give the easily separable crystalline exo and endo diastereomers 3x and 3n in yields of 54% and 36%, respectively. Catalytic hydrogenation of the enone of 3x followed by reduction with sodium borohydride gave, via the saturated ketone 4, the exo alcohol 5x in 54% overall yield along with a small amount of the endo stereoisomer 5n. Protection of the alcohol followed by addition of methyl Grignard produced, after hydrolysis of the intermediate imine and the silyl other, the desired 6-exo-acetyl-8-benzyl-8-azabicyclo [3.2.1]octan-2-exo-ol (8) in 71 % yield. The synthesis of Bao Gong Teng A (1) was completed by first effecting a Baeyer-Villiger oxidation of 8 to give N-benzyl Bao Gong Teng A (9) (54% yield) and then cleaving the N-benzyl group by hydrogenolysis to produce 1 in 74% yield, thereby ending an eight-step synthesis of Bao Gong Teng A (1) in 8% overall yield from readily available starting materials.

  DOI：

  10.1021/jo00039a005