(E)-1',2-dehydro-N-methylpelletierine | 137595-38-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (E)-1',2-dehydro-N-methylpelletierine
• 英文别名: (1E)-1-(1-methylpiperidin-2-ylidene)propan-2-one
• CAS: 137595-38-1
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: BAULNTCTTZYBGI-VQHVLOKHSA-N

物化性质

• 沸点：
  253.0±29.0 °C(Predicted)
• 密度：
  1.032±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-甲基-2-哌啶酮 在 diphosphorus pentasulfide 、 碳酸氢钠 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 36.0h， 生成 (E)-1',2-dehydro-N-methylpelletierine
  参考文献：
  名称：

  Late intermediates in the biosynthesis of cocaine: 4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate and methyl ecgonine

  摘要：

  Methyl (RS)-[1,2-C-13(2),1-C-14]-4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate was synthesized from a mixture of sodium [1,2-C-13(2)]- and (1-C-14]acetate. This beta-keto ester was administered to intact Erythroxylum coca plants, resulting in the formation of labeled cocaine and methyl ecgonine. The presence of contiguous C-13 atoms in these alkaloids at C-2 and C-9 was established by C-13 NMR spectroscopy, and the presence of C-14 at C-9 was established by a chemical degradation. These results are consistent with our new hypothesis for the biosynthesis of cocaine, which involves the intermediacy of 4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate (rather than 2-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate) in the formation of the tropane moiety of cocaine. Support for this biogenetic scheme was also obtained by a biomimetic synthesis of 2-carbomethoxy-3-tropinone by the oxidation of methyl 4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate with mercuric acetate. The formation of labeled cocaine and methyl ecgonine in leaf cuttings of Erythroxylum coca was observed after incubation with. [9-C-14]-2-carbomethoxy-3-tropinone. The degree of incorporation of this precursor into cocaine was significantly increased by the concomitant administration of the N-acetylcysteamine thioester of benzoic acid, with a corresponding reduction in the degree of incorporation into methyl ecgonine.

  DOI：

  10.1021/ja00024a039