(+/-)-(1R,2S,5R,6S)-6-acetyloxy-8-azabicyclo[3.2.1]octan-2-ol | 74239-84-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: (+/-)-(1R,2S,5R,6S)-6-acetyloxy-8-azabicyclo[3.2.1]octan-2-ol
• 英文别名: Bao Gong Teng A；(+/-)-BaO Gong Teng A；[(1S,2R,5S,6R)-2-hydroxy-8-azabicyclo[3.2.1]octan-6-yl] acetate
• CAS: 74239-84-2；107596-26-9；126640-93-5
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: FSXBMHMVOFJROW-RBXMUDONSA-N

物化性质

• 熔点：
  76-78 °C
• 沸点：
  302.2±32.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  8-benzyl-6-exo-(acetyloxy)-8-azabicyclo<3.2.1>octan-2-exo-ol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 60.0 ℃ 、303.97 kPa 条件下， 反应 4.0h， 以74%的产率得到(+/-)-(1R,2S,5R,6S)-6-acetyloxy-8-azabicyclo[3.2.1]octan-2-ol
  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

文献信息

• Organometallic Enantiomeric Scaffolding:  Organometallic Chirons. Total Synthesis of (−)-Bao Gong Teng A by a Molybdenum-Mediated [5+2] Cycloaddition
  作者：Yongqiang Zhang、Lanny S. Liebeskind

  DOI：10.1021/ja055623x

  日期：2006.1.1

  Bao Gong Teng A, an optically active tropane alkaloid with hypotensive and miotic activity isolated from the Chinese herb Erycibe obtusifolia Benth, was synthesized by an "organometallic Chiron" strategy in which single enantiomers of TpMo(CO)(2)(eta(3)-pyriclinyl) complexes are produced in quantity and then elaborated easily and efficiently to generate, after demetalation, highly enantiopure advanced synthetic intermediates possessing the tropane core.