4,5α-epoxy-6α,14-etheno-3,6-dimethoxy-17-methyl-2',5',7β,8β-tetrahydro-1'H-14α-pyrrolo[3',4':7,8]morphinan-2',5'-dione | 34766-01-3

• 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: 4,5α-epoxy-6α,14-etheno-3,6-dimethoxy-17-methyl-2',5',7β,8β-tetrahydro-1'H-14α-pyrrolo[3',4':7,8]morphinan-2',5'-dione
• 英文别名: 4,5α-epoxy-3,6-dimethoxy-17-methyl-6α,14α-etheno-morphinane-7α,8α-dicarboxylic acid imide
• CAS: 34766-01-3
• 化学式: C₂₃H₂₄N₂O₅
• 分子量: 408.454
• InChiKey: ACTIVTZSDMDJPA-VTUSGODYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  30.0
• 可旋转键数：
  2.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  77.1
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4,5α-epoxy-6α,14-etheno-3,6-dimethoxy-17-methyl-2',5',7β,8β-tetrahydro-1'H-14α-pyrrolo[3',4':7,8]morphinan-2',5'-dione 在 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4,5α-epoxy-3,6-dimethoxy-17-methyl-6α,14α-etheno-morphinane-7α,8α-dicarboxylic acid 2-(4-methyl-piperazin-1-yl)-2-oxo-ethylimide
  参考文献：
  名称：

  Thebain?Maleinimid-und Thebain?N-substituierte Maleinimid-Addukte

  摘要：

  DOI：

  10.1007/bf00909927
• 作为产物：
  描述：

  蒂巴因 在 sodium hydroxide 、 双氧水 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 4,5α-epoxy-6α,14-etheno-3,6-dimethoxy-17-methyl-2',5',7β,8β-tetrahydro-1'H-14α-pyrrolo[3',4':7,8]morphinan-2',5'-dione
  参考文献：
  名称：

  Thebain?Maleinimid-und Thebain?N-substituierte Maleinimid-Addukte

  摘要：

  DOI：

  10.1007/bf00909927

文献信息

• Synthetic transformations of isoquinoline alkaloids. Synthesis of 1-halo derivatives of endo-ethenotetrahydrothebaine and their behavior in the heck reaction
  作者：V. T. Bauman、E. E. Shul’ts、M. M. Shakirov、G. A. Tolstikov

  DOI：10.1134/s1070428007040070

  日期：2007.4

  Bromination of endo-ethenotetrahydrothebaine derivatives having a pyrrolidine ring fused at the C-7-C-8 stop bond, namely 1'-substituted 4,5 alpha-epoxy-6 alpha,14-etheno-3,6-dimethoxy-17-methyl-2',5',7 beta,8 beta-tetrahydro-1'H-14 alpha-pyrrolo[3',4':7,8]morphinan-2',5'-diones, 1'-aryl-4,5 alpha-epoxy-6 alpha,14-etheno-3,6-dimethoxy-17-methyl-2',5',7 beta,8 beta-tetrahydro-1'H-14 alpha-pyrrolo[3',4':7,8]morphinans, and 4,5 alpha-epoxy-6 alpha,14-etheno-2'+/--hydroxy-3,6- dimethoxy-17-methyl-1'-phenyl-2',5',7 beta,8 beta-tetrahydro-1'H-14 alpha-pyrrolo[3',4':7,8]morpphinan-5'-one, with molecular bromine in formic acid smoothly afforded the corresponding 1-bromo derivatives. Iodination of 4,5 alpha-epoxy-6 alpha,14-etheno-3,6-dimethoxy-17-methyl-1'-phenyl-2',5',7 beta,8 beta-tetrahydro-1'H-14 alpha-pyrrolo[3',4':7,8]-4,5 alpha-epoxy-6 alpha,14-etheno-3,6-dimethoxy-17-methyl-1'-phenyl-2',5',7 beta,8 beta-tetrahydro-1'H-14 alpha-pyrrolo[3',4':7,8]-morphinan-2',5'-dione with iodine(I) chloride gave 4,5 alpha-epoxy-6 alpha,14-etheno-1-iodo-3,6-dimethoxy-17-methyl-1'-phenyl-2',5',7 beta,8 beta-tetrahydro-1'H-14 alpha-pyrrolo[3',4':7,8]morphinan-2',5'-dione. The resulting 1-halo derivatives were brought into the Heck reaction with acrylic acid esters to obtain 1-[(E)-2-(alkoxycarbonyl)ethenyl]-substituted compounds. Demethylation of the 6-methoxy group in 1-bromo-endo-ethenotetrahydrothebaines was accomplished using boron(III) bromide in chloroform.