oripavine hydrochloride | 6153-40-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: oripavine hydrochloride
• 英文别名: 4,5α-epoxy-6-methoxy-17-methyl-morphina-6,8-dien-3-ol; hydrochloride；(4R,7aR,12bS)-7-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-ol;hydrochloride
• CAS: 6153-40-8
• 化学式: C₁₈H₁₉NO₃*ClH
• 分子量: 333.815
• InChiKey: OGVCGIJVSVSIEL-HIMTYSBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  41.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  oripavine hydrochloride 在 间氯过氧苯甲酸 、 盐酸 、 二茂铁基乙酸 作用下， 以 氯仿 、 异丙醇 为溶剂， 反应 16.33h， 以82%的产率得到N-nororipavine hydrochloride
  参考文献：
  名称：

  Polonovski-Type N-Demethylation of N-Methyl Alkaloids Using Substituted Ferrocene Redox Catalysts

  摘要：

  Various substituted ferrocenes have been trialed as catalysts in the nonclassical Polonovski reaction for N-demethylation of N-methyl alkaloids. Earlier studies suggest that conditions facilitating a higher ferrocenium ion concentration lead to superior outcomes. In this regard, the bifunctional ferrocene FcCH(2)CO(2)H, with electron donor and acceptor moieties in the same molecule, has been shown to be advantageous for use as a catalyst in the N-demethylation of a number of tertiary N-methylamines such as codeine, thebaine, and oripavine. These substrates are readily N-demethylated under mild conditions, employing sub-stoichiometric amounts of the substituted ferrocene at ambient temperature. These reactions are equally efficient in air and may also be carried out in one pot.

  DOI：

  10.1055/s-0032-1316590
• 作为产物：
  描述：

  oripavine N-oxide hydrochloride 在 二茂铁基乙酸 作用下， 以 氯仿 、 异丙醇 为溶剂， 反应 48.0h， 以82%的产率得到N-nororipavine hydrochloride
  参考文献：
  名称：

  Polonovski-Type N-Demethylation of N-Methyl Alkaloids Using Substituted Ferrocene Redox Catalysts

  摘要：

  Various substituted ferrocenes have been trialed as catalysts in the nonclassical Polonovski reaction for N-demethylation of N-methyl alkaloids. Earlier studies suggest that conditions facilitating a higher ferrocenium ion concentration lead to superior outcomes. In this regard, the bifunctional ferrocene FcCH(2)CO(2)H, with electron donor and acceptor moieties in the same molecule, has been shown to be advantageous for use as a catalyst in the N-demethylation of a number of tertiary N-methylamines such as codeine, thebaine, and oripavine. These substrates are readily N-demethylated under mild conditions, employing sub-stoichiometric amounts of the substituted ferrocene at ambient temperature. These reactions are equally efficient in air and may also be carried out in one pot.

  DOI：

  10.1055/s-0032-1316590

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF MORPHINANE AND MORPHINONE COMPOUNDS<br/>[FR] PROCÉDÉS POUR LA PRÉPARATION DE COMPOSÉS DE MORPHINANE ET DE MORPHINONE
  申请人：UNIV BROCK

  公开号：WO2010121369A1

  公开（公告）日：2010-10-28

  The present application describes processes for the synthesis of morphinane and morphinone compounds, useful as pharmaceutical agents. Also included are novel intermediates useful in the preparation of these compounds. The process comprises quaternization of oripavine to provide a mixture of the R- and S-isomeric (at the nitrogen) quaternary salts. The R-isomer is readily isolated and converted to various N-(R)-morphinane and N-(S)-morphinone compounds. The R-isomer, S-isomer or a mixture of R- and S-isomers may be demethylated and converted to various morphinane and morphinone compounds.

  本申请描述了合成吗啡烷和吗啡酮化合物的过程，这些化合物可用作药物。还包括在制备这些化合物过程中有用的新型中间体。该过程包括对奥利帕定进行季铵化，以提供R-和S-异构体（在氮上）季铵盐的混合物。R-异构体容易被分离并转化为各种N-(R)-吗啡烷和N-(S)-吗啡酮化合物。R-异构体、S-异构体或R-和S-异构体的混合物可以被去甲基化并转化为各种吗啡烷和吗啡酮化合物。
• Processes for the Preparation of Morphinane and Morphinone Compounds
  申请人：Hudlicky Tomas

  公开号：US20120046465A1

  公开（公告）日：2012-02-23

  The present application describes processes for the synthesis of morphinane and morphinone compounds, useful as pharmaceutical agents. Also included are novel intermediates useful in the preparation of these compounds. The process comprises quaternization of oripavine to provide a mixture of the R- and S-isomeric (at the nitrogen) quaternary salts. The R-isomer is readily isolated and converted to various N-(R)-morphinane and N-(S)-morphinone compounds. The R-isomer, S-isomer or a mixture of R- and S-isomers may be demethylated and converted to various morphinane and morphinone compounds.

  本申请描述了合成吗啡烷和吗啡酮化合物的过程，这些化合物可用作药物。还包括在制备这些化合物中有用的新型中间体。该过程包括对烟阔叶芥子碱进行季铵化，以提供R-和S-异构体（在氮上）季铵盐的混合物。R-异构体易于分离并转化为各种N-（R）-吗啡烷和N-（S）-吗啡酮化合物。R-异构体、S-异构体或R-和S-异构体的混合物可以去甲基化并转化为各种吗啡烷和吗啡酮化合物。
• PROCESSES FOR THE PREPARATION OF MORPHINANE AND MORPHINONE COMPOUNDS
  申请人：Brock University

  公开号：EP2421868A1

  公开（公告）日：2012-02-29
• US8853401B2
  申请人：——

  公开号：US8853401B2

  公开（公告）日：2014-10-07
• Polonovski-Type N-Demethylation of N-Methyl Alkaloids Using Substituted Ferrocene Redox Catalysts
  作者：Peter Scammells、Gaik Kok

  DOI：10.1055/s-0032-1316590

  日期：2012.8

  Various substituted ferrocenes have been trialed as catalysts in the nonclassical Polonovski reaction for N-demethylation of N-methyl alkaloids. Earlier studies suggest that conditions facilitating a higher ferrocenium ion concentration lead to superior outcomes. In this regard, the bifunctional ferrocene FcCH(2)CO(2)H, with electron donor and acceptor moieties in the same molecule, has been shown to be advantageous for use as a catalyst in the N-demethylation of a number of tertiary N-methylamines such as codeine, thebaine, and oripavine. These substrates are readily N-demethylated under mild conditions, employing sub-stoichiometric amounts of the substituted ferrocene at ambient temperature. These reactions are equally efficient in air and may also be carried out in one pot.