N-Methyl-Δ¹-pyrroliniumchlorid | 18028-53-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: N-Methyl-Δ¹-pyrroliniumchlorid
• 英文别名: 1-Methyl-1-pyrrolinium chloride；1-methyl-3,4-dihydro-2H-pyrrol-1-ium;chloride
• CAS: 18028-53-0
• 化学式: C₅H₁₀N*Cl
• 分子量: 119.594
• InChiKey: NREMTFDBMWJFQE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-Methyl-Δ¹-pyrroliniumchlorid 、 <2-13C>ethyl acetoacetate 以 乙醇 、 水 为溶剂， 反应 120.0h， 生成
  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
• 作为产物：
  描述：

  γ-甲基氨基丁醛乙酸二乙酯 在 盐酸 作用下， 生成 N-Methyl-Δ¹-pyrroliniumchlorid
  参考文献：
  名称：

  Nicotine synthase - an enzyme from nicotiana species which catalyzes the formation of (S)-nicotine from nicotinic acid and 1-methyl-δ'pyrrolinium chloride

  摘要：

  DOI：

  10.1016/s0040-4039(00)97046-1

文献信息

• FRIESEN, BRENT J.;LEETE, EDWARD, TETRAHEDRON LETT., 31,(1990) N4, C. 6295-6298
  作者：FRIESEN, BRENT J.、LEETE, EDWARD

  DOI：——

  日期：——