1-(2-chloro-4,5-dihydroxybenzyl)-1,2,3,4,8,8a-hexahydroisoquinolin-6(7H)-one | 886836-15-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-(2-chloro-4,5-dihydroxybenzyl)-1,2,3,4,8,8a-hexahydroisoquinolin-6(7H)-one
• 英文别名: 1-[(2-chloro-4,5-dihydroxyphenyl)methyl]-2,3,4,7,8,8a-hexahydro-1H-isoquinolin-6-one
• CAS: 886836-15-3
• 化学式: C₁₆H₁₈ClNO₃
• 分子量: 307.777
• InChiKey: LBYNOXVFIMUWQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

文献信息

• Processes for preparing morphinans and intermediates thereof
  申请人：Mallinckrodt Inc.

  公开号：EP2199285A1

  公开（公告）日：2010-06-23

  The present invention is directed to processes for the synthesis of morphinans. In particular, a process for cyclizing a β,γ-bicyclic ketone compound to form a nordihydrothebainone product using the Grewe cyclization reaction is improved by forming a reaction mixture comprising a β.γ-bicyclic ketone compound, a cyclizing acid and a water scavenging cyclization additive. In one embodiment, the Grewe transformation occurs in the presence of an acid anhydride as the cyclization additive. Further, the present invention is directed to processes for converting α,β-bicyclic ketone compounds (e.g., by-products of the Grewe cyclization reaction) to β,γ-bicyclic ketone compounds, wherein the β,γ-bicyclic ketone compounds may be recovered to further undergo Grewe cyclization and form the nordihydrothebainone product.

  本发明涉及吗啡类化合物的合成工艺。特别是通过形成一种包含β.γ-双环酮化合物、一种环化酸和一种水清除环化添加剂的反应混合物，改进了利用格氏环化反应使β,γ-双环酮化合物环化以形成一种去氢吗啡酮产物的工艺。在一个实施方案中，格氏转化是在酸酐作为环化添加剂存在的情况下进行的。此外，本发明还涉及将 α，β-双环酮化合物（例如，格列卫环化反应的副产物）转化为 β，γ-双环酮化合物的工艺，其中 β，γ-双环酮化合物可回收以进一步进行格列卫环化反应并形成正二氢土荆皮酮产品。
• OPIATE INTERMEDIATES AND METHODS OF SYNTHESIS
  申请人：MALLINCKRODT, INC.

  公开号：EP1812399A2

  公开（公告）日：2007-08-01
• PROCESSES FOR PREPARING MORPHINANS AND INTERMEDIATES THEREOF
  申请人：MALLINCKRODT, INC.

  公开号：EP1861373A2

  公开（公告）日：2007-12-05
• Opiate Intermediates and Methods of Synthesis
  申请人：Wang Xianqi Peter

  公开号：US20070244151A1

  公开（公告）日：2007-10-18

  Novel opiate intermediate compositions and methods of synthesis that include changing the substitution pattern on the aromatic ring of the pre-Grewe intermediate are provided.
• Processes for Preparing Morphinans and Intermediates Thereof
  申请人：Wang Peter Xianqi

  公开号：US20080262231A1

  公开（公告）日：2008-10-23

  The present invention is directed to processes for the synthesis of morphinans. In particular, a process for cyclizing a β,γ-bicyclic ketone compound to form a nordihydrothebainone product using the Grewe cyclization reaction is improved by forming a reaction mixture comprising a β,γ-bicyclic ketone compound, a cyclizing acid and a water scavenging cyclization additive. In one embodiment, the Grewe transformation occurs in the presence of an acid anhydride as the cyclization additive. Further, the present invention is directed to processes for converting α,β-bicyclic ketone compounds (e.g., by-products of the Grewe cyclization reaction) to β,γ-bicyclic ketone compounds, wherein the β,γ-bicyclic ketone compounds may be recovered to further undergo Grewe cyclization and form the nordihydrothebainone product.