8-氮杂双环[3.2.1]辛-2-烯-2-羧酸8-甲基-乙酯 | 73045-45-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 8-氮杂双环[3.2.1]辛-2-烯-2-羧酸8-甲基-乙酯
• 英文名称: anhydroecgonine ethyl ester
• 英文别名: Ecgonidine ethyl ester；ethyl (1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate
• CAS: 73045-45-1
• 化学式: C₁₁H₁₇NO₂
• 分子量: 195.261
• InChiKey: YNQKCHQJQNRNHW-PSASIEDQSA-N

物化性质

• 溶解度：
  氯仿（少量溶解）、二氯甲烷（少量，超声处理）、乙酸乙酯（少量溶解）

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-氮杂双环[3.2.1]辛-2-烯-2-羧酸8-甲基-乙酯 生成 cyclohepta-2,4,6-trienecarboxylic acid-(4-bromo-phenacyl ester)
  参考文献：
  名称：

  Alder et al., Justus Liebigs Annalen der Chemie, 1957, vol. 602, p. 80,92

  摘要：

  DOI：
• 作为产物：
  描述：

  乙醇 、 古卡因 在 盐酸 、 三氯氧磷 作用下， 以 水 为溶剂， 反应 108.0h， 生成 8-氮杂双环[3.2.1]辛-2-烯-2-羧酸8-甲基-乙酯
  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

• METHOD FOR PRODUCING (1R,5S) ANHYDROECGONINE ESTER SALTS
  申请人：Puder Carsten H.

  公开号：US20100331544A1

  公开（公告）日：2010-12-30

  The invention relates to a large-scale method for producing salts of (IR,5S) anhydroecgonine esters. The salt formation and selective crystallization of (IR,5S) anhydroecgonine esters with chiral acids is highly efficient in producing an enantiomer form, any undesired enantiomers and other impurities being removed. The ester and its salts are used as the starting material for producing active agents.

  该发明涉及一种大规模生产（IR,5S）缺水异香草碱酯盐的方法。利用手性酸与（IR,5S）缺水异香草碱酯的盐形成和选择性结晶，在生产对映体形式上高效，任何不需要的对映体和其他杂质都被去除。该酯及其盐被用作生产活性剂的起始物质。
• [EN] PROCESS FOR PREPARING ENANTIOMERICALLY ENRICHED ALKALOIDS<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ALCALOÏDES ENRICHIS SUR LE PLAN ÉNANTIOMÈRE
  申请人：CAMBREX KARLSKOGA AB

  公开号：WO2010086612A1

  公开（公告）日：2010-08-05

  There is provided a process for the preparation of a single enantiomer of anhydroecgonine of formula (I), or a salt thereof, in which R1 is as defined in the description. Such single enantiomers may, for example, be useful intermediates in the synthesis of pharmaceuticals, in which the enantioselectivity is important.

  提供了一种制备式(I)的单对映体或其盐的过程，其中R1如描述中定义。这种单对映体可能在制药合成中起到重要作用，其中对映选择性很重要。
• Azabicyclo and azacyclo oxime and amine cholinergic agents and methods
  申请人：Warner-Lambert Company

  公开号：US05482938A1

  公开（公告）日：1996-01-09

  Pharmaceutically useful nitrogen containing cyclic oxime and amine substituted compounds are disclosed which are azabicyclo[2.2.2]oximes, azabicyclo[2.2.2]-amines, azabicyclo[3.2.1]oximes and amine containing heterocyclic oximes wherein the heterocyclic ring contains from 3 to 7 carbon atoms.

  本文披露了一些具有药用价值的氮杂环氧酮和胺取代化合物，包括：含有氮杂环[2.2.2]氧酮、含有氮杂环[2.2.2]胺、含有氮杂环[3.2.1]氧酮和含有胺基的杂环氧酮，其中杂环环中含有3至7个碳原子。
• Oxime and amine substituted azabicyclo and azocyclo muscarinic agonists
  申请人：Warner-Lambert Company

  公开号：US05306718A1

  公开（公告）日：1994-04-26

  Pharmaceutically useful nitrogen containing cyclic oxime and amine substituted compounds of the following general Formulas I, II and III are disclosed: ##STR1## Specifically the compounds are azabicyclo [2.2.1] omimes, azabicyclo [2.2.2] oximes, azabicyclo [2.2.1] amines, azabicyclo [2.2.2] amines, azabicyclo [3.2.1] oximes and amine containing heterocyclic oximes wherein the heterocyclic ring contains from 4 to 5 [3 to 7] carbon atoms.

  本文披露了具有以下一般式I、II和III的含有氮的环氧肟和胺取代化合物，其在药学上有用：##STR1## 具体来说，这些化合物是氮杂双环[2.2.1]肟，氮杂双环[2.2.2]肟，氮杂双环[2.2.1]胺，氮杂双环[2.2.2]胺，氮杂双环[3.2.1]肟和含有杂环肟的胺，其中杂环环中含有4至5 [3至7]个碳原子。
• Azabicyclo and azacyclo oxime and amine cholinergic agents and pharmaceutically acceptable salts thereof
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0445731A1

  公开（公告）日：1991-09-11

  Pharmaceutically useful nitrogen containing cyclic oxime and amine substituted compounds of the formula which are azabicyclo[2.2.1]oximes, azabizyclo[2.2.2]oximes, azabicyclo[2.2.1]amines, azabicyclo[2.2.2]amines, azabicyclo[3.2.1]oximes and amine containing heterocyclic oximes wherein the heterocyclic ring contains from 3 to 7 carbon atoms. These compounds are useful as analgesics and for the treatment of cognitive decline in a patient.

  药用含氮环肟和胺取代的式化合物 其中包括氮杂双环[2.2.1]肟、氮杂双环[2.2.2]肟、氮杂双环[2.2.1]胺、氮杂双环[2.2.2]胺、氮杂双环[3.2.1]肟和含胺杂环肟，其中杂环含有 3 至 7 个碳原子。这些化合物可用作镇痛剂和治疗患者认知能力下降。