1'-benzyl-[7α,8α:3',4']-pyrrolidino-6,14-endoethenotetrahydrothebaine | 34156-07-5

• 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-[7α,8α:3',4']-pyrrolidino-6,14-endoethenotetrahydrothebaine
• 英文别名: 1'-benzyl-4,5α-epoxy-3,6-dimethoxy-17-methyl-(7β,8β)-8,1',2',5'-tetrahydro-7H-6α,14α-etheno-pyrrolo[3',4':7,8]morphinane；(1S,2S,6R,14R,15R,16R,20R)-18-benzyl-11,15-dimethoxy-5-methyl-13-oxa-5,18-diazaheptacyclo[13.5.2.12,8.01,6.02,14.016,20.012,23]tricosa-8(23),9,11,21-tetraene
• CAS: 34156-07-5
• 化学式: C₃₀H₃₄N₂O₃
• 分子量: 470.612
• InChiKey: HAKABJLUFLMGJQ-BBFMNQIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  34.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1'-benzyl-[7α,8α:3',4']-pyrrolidino-6,14-endoethenotetrahydrothebaine 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 120.0h， 以22%的产率得到[7α,8α:3',4']-pyrrolidino-6,14-endoethenotetrahydrothebaine
  参考文献：
  名称：

  Cinnamoyl Derivatives of 7α-Aminomethyl-6,14-endo-ethanotetrahydrothebaine and 7α-Aminomethyl-6,14-endo-ethanotetrahydrooripavine and Related Opioid Ligands

  摘要：

  A new series of ligands has been synthesized where the cinnamoyl group of the 14-cinnamoylamino morphinones has been introduced to the 7 alpha-substituent of the 6,14-bridged oripavine series. In vitro the compounds were mostly low efficacy partial agonists or antagonists with some selectivity for the mu opioid receptor, with evidence of mu efficacy in vivo. The similarity in SAR between these 6,14-bridged oripavines and the 14-cinnamoylamino series suggests a similar mode of interaction with the mu. opioid receptor.

  DOI：

  10.1021/jm070255o
• 作为产物：
  描述：

  蒂巴因 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 1'-benzyl-[7α,8α:3',4']-pyrrolidino-6,14-endoethenotetrahydrothebaine
  参考文献：
  名称：

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

  摘要：

  DOI：

  10.1007/bf00909927

文献信息

• Cinnamoyl Derivatives of 7α-Aminomethyl-6,14-<i>endo</i>-ethanotetrahydrothebaine and 7α-Aminomethyl-6,14-<i>endo</i>-ethanotetrahydrooripavine and Related Opioid Ligands
  作者：David Rennison、Adrian P. Neal、Gerta Cami-Kobeci、Mario D. Aceto、Fernando Martinez-Bermejo、John W. Lewis、Stephen M. Husbands

  DOI：10.1021/jm070255o

  日期：2007.10.1

  A new series of ligands has been synthesized where the cinnamoyl group of the 14-cinnamoylamino morphinones has been introduced to the 7 alpha-substituent of the 6,14-bridged oripavine series. In vitro the compounds were mostly low efficacy partial agonists or antagonists with some selectivity for the mu opioid receptor, with evidence of mu efficacy in vivo. The similarity in SAR between these 6,14-bridged oripavines and the 14-cinnamoylamino series suggests a similar mode of interaction with the mu. opioid receptor.
• Thebain?Maleinimid-und Thebain?N-substituierte Maleinimid-Addukte
  作者：O. Hromatka、G. Sengstschmid、K. Eichinger

  DOI：10.1007/bf00909927

  日期：——