1-benzyl-6,7-didehydro-4,5α-epoxy-4',5'-dihydro-3,14-dihydroxy-17-methylpyrido[2',3':6,7]morphinan-6'(1'H)-one

• 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-benzyl-6,7-didehydro-4,5α-epoxy-4',5'-dihydro-3,14-dihydroxy-17-methylpyrido[2',3':6,7]morphinan-6'(1'H)-one
• 英文别名: (1S,2S,10R,18R)-8-benzyl-2,13-dihydroxy-19-methyl-11-oxa-8,19-diazahexacyclo[10.9.1.01,10.02,18.04,9.016,22]docosa-4(9),12,14,16(22)-tetraen-7-one
• 化学式: C₂₇H₂₈N₂O₄
• 分子量: 444.53
• InChiKey: BKWSYTVAXNIJBM-BQRPEJFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  氢羟吗啡酮 、 苄胺 、 丙烯酸乙酯 在 4 A molecular sieve 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以60%的产率得到1-benzyl-6,7-didehydro-4,5α-epoxy-4',5'-dihydro-3,14-dihydroxy-17-methylpyrido[2',3':6,7]morphinan-6'(1'H)-one
  参考文献：
  名称：

  Michael Reactions of Benzylimines Derived from Morphinan-6-ones: Synthesis of Pyrrolo- and Pyridinomorphinans

  摘要：

  The benzylimines 15 derived from oxymorphones 14 and generated in situ reacted with Michael acceptors (methyl methacrylate, maleic anhydride, and alpha-metlivlene-gamma-butyrolactone) to give opioid ligands 16, 17, and 19-21 having pyrrole- or pyridine-derived ring systems (see Scheme 3). The product of the reaction with maleic anhydride displayed a surprising preference for the 2-hydroxypyrrole form 19 rather than for the tautomeric 1.6-dihydro-2H-pyrrol-2-one form 24, resulting from the stability of the C(6)=C(7) bond in oxymorphone and related structures.

  DOI：

  10.1002/1522-2675(200206)85:6<1790::aid-hlca1790>3.0.co;2-g

文献信息

• Michael Reactions of Benzylimines Derived from Morphinan-6-ones: Synthesis of Pyrrolo- and Pyridinomorphinans
  作者：Shefali、Sanjay K. Srivastava、Lee D. Hall、John W. Lewis、Stephen M. Husbands

  DOI：10.1002/1522-2675(200206)85:6<1790::aid-hlca1790>3.0.co;2-g

  日期：2002.6

  The benzylimines 15 derived from oxymorphones 14 and generated in situ reacted with Michael acceptors (methyl methacrylate, maleic anhydride, and alpha-metlivlene-gamma-butyrolactone) to give opioid ligands 16, 17, and 19-21 having pyrrole- or pyridine-derived ring systems (see Scheme 3). The product of the reaction with maleic anhydride displayed a surprising preference for the 2-hydroxypyrrole form 19 rather than for the tautomeric 1.6-dihydro-2H-pyrrol-2-one form 24, resulting from the stability of the C(6)=C(7) bond in oxymorphone and related structures.