1'-benzyl-6,7-didehydro-4,5α-epoxy-3,5',14-trihydroxy-17-methyl-1'H-pyrrolo[2',3':6,7]morphinan-4'-acetic acid ethyl ester

• 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-3,5',14-trihydroxy-17-methyl-1'H-pyrrolo[2',3':6,7]morphinan-4'-acetic acid ethyl ester
• 英文别名: ethyl 2-[(1S,2S,9R,17R)-7-benzyl-2,6,12-trihydroxy-18-methyl-10-oxa-7,18-diazahexacyclo[9.9.1.01,9.02,17.04,8.015,21]henicosa-4(8),5,11,13,15(21)-pentaen-5-yl]acetate
• 化学式: C₃₀H₃₂N₂O₆
• 分子量: 516.594
• InChiKey: LWJQJBOPDYTMKC-KLNDKWMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  马来酸酐 、 乙醇 、 氢羟吗啡酮 、 苄胺 在 4 A molecular sieve 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以21%的产率得到1'-benzyl-6,7-didehydro-4,5α-epoxy-3,5',14-trihydroxy-17-methyl-1'H-pyrrolo[2',3':6,7]morphinan-4'-acetic acid ethyl ester
  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.