1-bromo-4-hydroxy-3,7-dimethoxy-17-methyl-morphin-7-en-6-one | 68160-79-2

• 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: 1-bromo-4-hydroxy-3,7-dimethoxy-17-methyl-morphin-7-en-6-one
• 英文别名: Morphinan-6-one, 1-bromo-7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-；(1S,9R,10R)-6-bromo-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2,4,6,11-tetraen-13-one
• CAS: 68160-79-2
• 化学式: C₁₉H₂₂BrNO₄
• 分子量: 408.292
• InChiKey: PHKNOXCRUVPZOB-XAEJFWIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-bromo-4-hydroxy-3,7-dimethoxy-17-methyl-morphin-7-en-6-one 在 溴 作用下， 以 氢溴酸 、 溶剂黄146 为溶剂， 生成 1-bromo-4,5α-epoxy-3,7-dimethoxy-17-methyl-morphin-7-en-6-one
  参考文献：
  名称：

  Synthesis and antinociceptive activity of 7-methoxycodeine

  摘要：

  (-)-7-甲氧基可待因从(-)-1-溴substitutesenonin酮经三步合成，总产率为29%。在可待因的C环中引入7-甲氧基基团并未降低其口服活性。7-甲氧基可待因在酸性介质中不稳定。然而，其口服活性不太可能由于转化为酸稳定的(-)-substitutesenonin酮，因为后者在口服下无效。

  DOI：

  10.1021/jm00210a031

文献信息

• [EN] SINOMENINE AND SINOMENINE COMPOUNDS, SYNTHESIS AND USE<br/>[FR] SINOMENINE ET COMPOSES DE SINOMENINE, PROCEDE DE SYNTHESE ASSOCIE ET UTILISATION ASSOCIEE
  申请人：SHANGHAI INST MATERIA MEDICA

  公开号：WO2004048340A1

  公开（公告）日：2004-06-10

  The invention relates to sinomenine and compounds thereof and also to compounds of formula (I), wherein R1 represents an alkyl group; R2 represents a hydrogen atom or an alkylcarbonyl group, an haloalkylcarbonyl group or an arylcarbonyl; Y represents a group (II), (III) or (IV); R3 ,R4, R’4, R5, R’5 and R6 are as defined in the description; and X represents a halogen atom. Medicaments.

  这项发明涉及青藤碱及其化合物，以及化合物的公式（I），其中R1代表烷基基团；R2代表氢原子或烷基羰基基团、卤代烷基羰基基团或芳基羰基；Y代表群（II）、（III）或（IV）；R3、R4、R’4、R5、R’5和R6如描述中所定义；X代表卤素原子。药物。
• Sinomenine and sinomenine compounds, synthesis and use
  申请人：Qin Guo-Wei

  公开号：US20060009480A1

  公开（公告）日：2006-01-12

  The invention relates to sinomenine and compounds thereof and also to compounds of formula (I): wherein R 1 represents alkyl, R 2 represents hydrogen or alkylcarbonyl, haloalkylcarbonyl or arylcarbonyl, Y represents a group R 3 , R 4 , R′ 4 , R 5 , R′ 5 and R 6 are as defined in the description, and X represents halogen and medicinal products containing the same which are useful in treating mnemocognitive disorders.

  本发明涉及西诺明及其化合物，还涉及式 (I) 化合物： 其中 R 1 代表烷基、 R 2 代表氢或烷基羰基、卤代烷基羰基或芳基羰基、 Y 代表一个基团 R 3 , R 4 , R′ 4 , R 5 , R′ 5 和 R 6 的定义，X 代表卤素和含有卤素的可用于治疗脑认知障碍的药物产品。
• SINOMENINE AND SINOMENINE COMPOUNDS, SYNTHESIS AND USE
  申请人：Shangai Institute of Materia Medica, Chinese Academy of Sciences

  公开号：EP1565444A1

  公开（公告）日：2005-08-24
• Synthesis and antinociceptive activity of 7-methoxycodeine
  作者：Ikuo Iijima、Junichi Minamikawa、Kenner C. Rice、Arthur E. Jacobson

  DOI：10.1021/jm00210a031

  日期：1978.12

  (-)-7-Methoxycodeine was synthesized from (-)-1-bromosinomeninone in three steps with an overall yield of 29%. The introduction of the 7-methoxy group into the C ring of codeine did not decrease its oral activity. 7-Methoxycodeine was unstable in acidic media. Its oral activity was however, not likely to be due to conversion to the acid-stable (-)-sinomeninone, since the latter was orally inactive.

  (-)-7-甲氧基可待因从(-)-1-溴substitutesenonin酮经三步合成，总产率为29%。在可待因的C环中引入7-甲氧基基团并未降低其口服活性。7-甲氧基可待因在酸性介质中不稳定。然而，其口服活性不太可能由于转化为酸稳定的(-)-substitutesenonin酮，因为后者在口服下无效。