(-)-11,11-Dimethyl-10,11-dihydropyranotropan-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (-)-11,11-Dimethyl-10,11-dihydropyranotropan-3-one
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: ZIFXMMFPWKWBEW-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  托品酮 在 chiral lithium amide 、 sodium carbonate 、 lithium chloride 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (-)-11,11-Dimethyl-10,11-dihydropyranotropan-3-one
  参考文献：
  名称：

  Synthesis of pyranotropanes via enantioselective deprotonation strategy

  摘要：

  Synthesis of tropane alkaloids darlingine, chalcostrobamine and isobellendine both in the racemic form and as unnatural enantiomers is described. Enantioselective deprotonation of tropinone, which proceeded with ca 90% ee, was the key step in each of the syntheses. Enantioselectivity was increased in the presence of LiCl.

  DOI：

  10.1016/s0040-4039(00)73063-2

文献信息

• Synthesis of Tropane Alkaloids via Enantioselective Deprotonation of Tropinone
  作者：Marek Majewski、Ryszard Lazny

  DOI：10.1021/jo00123a018

  日期：1995.9

  Enantioselective deprotonation of tropinone 2 with chiral lithium amides 5a and 6a, in the presence of LiCl, gave tropinone lithium enolate in up to 95% ee. The C-2 symmetrical lithium amide 6a worked best when it was generated in situ from the hydrochloride salt of the corresponding amine 6b. The deprotonation was used as the key step in synthesis of tropane alkaloids: ent-anhydroecgonine, ent-knightinol, KD-B, chalcostrobamine, ent-isobellendine, and ent-darlingine. The absolute configuration of natural benzyltropane and pyranotropane alkaloids was established (by correlation with anhydroecgonine) to be 'cocaine-like' i.e., the side chain originates at C-2 of the tropane ring system in all cases.