anhydronorecgonine methyl ester | 129944-82-7

• 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: anhydronorecgonine methyl ester
• 英文别名: noranhydroecgonine methyl ester；methyl (1R,5S)-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate
• CAS: 129944-82-7
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: DJXUOKXQNIBCET-HTRCEHHLSA-N

物化性质

• 沸点：
  251.4±28.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 anhydronorecgonine methyl ester 在 sodium cyanoborohydride 作用下， 生成 脱水芽子碱甲基酯甲磺酸盐
  参考文献：
  名称：

  Enantioselective Synthesis of Functionalized Tropanes by Rhodium(II) Carboxylate-Catalyzed Decomposition of Vinyldiazomethanes in the Presence of Pyrroles

  摘要：

  A series of enantiomerically enriched tropanes was synthesized by the rhodium(II) octanoate-catalyzed reaction of various N-BOC-protected pyrroles with vinyldiazomethanes. The overall 3 + 4 annulation occurs by a tandem cyclopropanation/Cope rearrangement. Asymmetric induction was best achieved in these transformations by using either (S)-lactate or (R)-pantolactone as a chiral auxiliary on the vinyldiazomethanes. Reactions carried out with the chiral catalyst tetrakis[N-( 4-tert-butylbenzenesulfonyl)-(L)-prolinato]dirhodium (2) provided moderate asymmetric induction, but also resulted in the formation of isomeric azabicyclooctane side products. The utility of the synthetic process was demonstrated through the asymmetric synthesis of(-)-anhydroecgonine methyl ester and (-)-ferruginine.

  DOI：

  10.1021/jo961920w
• 作为产物：
  描述：

  (1R,2R,3S,5S)-3-(苯甲酰氧基)-8-氮杂双环[3.2.1]辛烷-2-羧酸甲酯 在 盐酸 、 三氟化硼乙醚 作用下， 反应 28.0h， 生成 anhydronorecgonine methyl ester
  参考文献：
  名称：

  Studies on Hydrolytic and Oxidative Metabolic Pathways of Anhydroecgonine Methyl Ester (Methylecgonidine) Using Microsomal Preparations from Rat Organs

  摘要：

  During smoking of cocaine-base (crack), anhydroecgonine methyl ester (AEME, methylecgonidine) is formed in large amounts as a pyrolysis product of cocaine and is absorbed in the lungs. The metabolism of AEME was studied in the present investigation using microsome preparations from rat liver, lung, kidney, and brain. Potential metabolites of AEME were synthesized and used as substrate to complement the experiments. Analysis of the incubation mixtures was performed using gas chromatography-mass spectrometry and nanoelectrospray multiple-stage mass spectrometry. Screening for metabolites was focused on postulated oxidative pathways, chemical and enzymatic hydrolysis, and ethanol dependent transesterification as known from cocaine metabolism. Enzymatic hydrolysis of AEME to anhydroecgonine (AE), which was inhibited by sodium fluoride, was found in all microsomal preparations. Liver microsomes exhibited the highest activity, brain microsomes the lowest. Anhydronorecgonine methyl ester (ANEME) and anhydroecgonine methyl ester N-oxide were identified as AEME metabolites of liver and lung microsomes only. In the presence of ethanol AEME was metabolized to anhydroecgonine ethyl ester and anhydronorecgonine ethyl ester. Further metabolism of AE or ANEME was not observed. No N-hydroxy-anhydronorecgonine derivatives were found which could represent precursors of cytotoxic metabolites as known to be formed from cocaine.

  DOI：

  10.1021/tx0255828

文献信息

• PROCESS FOR THE PREPARATION OF RADIOIODINATED 3-FLUOROPROPYL-NOR-Beta-CIT
  申请人：MALLINCKRODT LLC

  公开号：US20150087838A1

  公开（公告）日：2015-03-26

  The invention generally provides processes for the preparation of radioiodinated 3-fluoropropyl-nor-β-CIT. In particular, the process uses an arylsilane intermediate, thus avoiding the use of hexamethylditin, and reducing the number of steps previously required for the preparation of radioiodinated 3-fluoropropyl-nor-β-CIT from anhydroecgonine methyl ester. The invention also relates to the alkylation of a nortropane to the corresponding N-(3-fluoropropyl) analogue using 3-fluoropropanal.

  该发明通常提供了用于制备放射性碘化3-氟丙基-去-β-CIT的方法。具体而言，该过程使用芳基硅烷中间体，从而避免使用六甲基锡，减少以前从去水基甲基植物碱制备放射性碘化3-氟丙基-去-β-CIT所需的步骤数量。该发明还涉及利用3-氟丙醛对去幽梗烷烃进行烷基化，形成相应的N-(3-氟丙基)类似物。
• US9339565B2
  申请人：——

  公开号：US9339565B2

  公开（公告）日：2016-05-17