benzoylecgonine | 134623-91-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzoylecgonine
• CAS: 134623-91-9
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: GVGYEFKIHJTNQZ-RQJABVFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 benzoylecgonine 以 二氯甲烷 为溶剂， 生成 (+/-)-cocaine
  参考文献：
  名称：

  Enantiospecific Synthesis of Natural (−)-Cocaine and Unnatural (+)-Cocaine from d- and l-Glutamic Acid

  摘要：

  Natural (-)-cocaine and unnatural (+)-cocaine have been synthesized enantiospecifically from D- and L-glutamic acid, respectively. The axial-equatorial substitutents were introduced by a stereo- and regiospecific dipolar cycloaddition to the corresponding (LR,5S)- and (1S,5R)-N-BOC-nortropenes with (ethoxycarbonyl)formonitrile N-oxide. A sequence of subsequent stereochemically controlled transformations converted the fused isoxazoline to the requisite P-hydroxy ester. Synthesis of the key intermediate N-BOC-nortropenes involved construction of the 8-azabicyclo[3.2.1]octane framework by Dieckmann condensation of cis-5-substituted D-and L-proline esters. For comparison, (1R,SS)-N-BOC-nortropene also was derived by degradation from natural cocaine. The cis-5-substituted D-and L-proline esters were obtained by sulfide contraction and subsequent catalytic hydrogenation to induce stereospecifically the C-5 stereochemistry from D-and L-thiopyroglutamate, which in turn were prepared from D-and L-glutamic acids, respectively.

  DOI：

  10.1021/jo980153t
• 作为产物：
  描述：

  [(1S,2S,3R,5R)-2-carbamoyl-8-azabicyclo[3.2.1]octan-3-yl] benzoate 在 sodium cyanoborohydride 、 sodium nitrite 作用下， 以 乙酸酐 、 溶剂黄146 、 乙腈 为溶剂， 反应 25.0h， 生成 benzoylecgonine
  参考文献：
  名称：

  Enantiospecific Synthesis of Natural (−)-Cocaine and Unnatural (+)-Cocaine from d- and l-Glutamic Acid

  摘要：

  Natural (-)-cocaine and unnatural (+)-cocaine have been synthesized enantiospecifically from D- and L-glutamic acid, respectively. The axial-equatorial substitutents were introduced by a stereo- and regiospecific dipolar cycloaddition to the corresponding (LR,5S)- and (1S,5R)-N-BOC-nortropenes with (ethoxycarbonyl)formonitrile N-oxide. A sequence of subsequent stereochemically controlled transformations converted the fused isoxazoline to the requisite P-hydroxy ester. Synthesis of the key intermediate N-BOC-nortropenes involved construction of the 8-azabicyclo[3.2.1]octane framework by Dieckmann condensation of cis-5-substituted D-and L-proline esters. For comparison, (1R,SS)-N-BOC-nortropene also was derived by degradation from natural cocaine. The cis-5-substituted D-and L-proline esters were obtained by sulfide contraction and subsequent catalytic hydrogenation to induce stereospecifically the C-5 stereochemistry from D-and L-thiopyroglutamate, which in turn were prepared from D-and L-glutamic acids, respectively.

  DOI：

  10.1021/jo980153t

文献信息

• [EN] METHODS FOR PRODUCING HYDROXYALKYL TROPANE ESTERS<br/>[FR] PROCÉDÉS DE PRODUCTION D'HYDROXYALKYL TROPANE ESTERS
  申请人：ENTROPIN INC

  公开号：WO2004018464A1

  公开（公告）日：2004-03-04

  This invention provides a method for preparing a hydroxyalkyl tropane ester, comprising: (a) contacting a tropane and 1,1'-carbonyldiimidazole to produce an activated tropane ester; (b) contacting the activated tropane ester with an excess of an alkanediol to form a reaction mixture; and (c) maintaining the reaction mixture at a temperature and for a sufficient time for the activated tropane ester to react with the alkanediol to form the corresponding hydroxyalkyl tropane ester. This method may be used to produce hydroxyalkyl derivatives of tropanes such as benzoylecgonine, ecgonine and ecgonidine.

  本发明提供了一种制备羟基烷基曲柳酯的方法，包括：（a）将曲柳和1,1'-羰基二咪唑接触以产生活化的曲柳酯；（b）将活化的曲柳酯与过量的脂肪二醇接触以形成反应混合物；并且（c）在足够的时间内将反应混合物保持在一定的温度下，使活化的曲柳酯与脂肪二醇反应形成相应的羟基烷基曲柳酯。该方法可用于生产苯甲酰异可卡因、异可卡因和异可吡啶等曲柳酯的羟基烷基衍生物。