(4bS,8R,8aS,14bR)-5,6,7,8,14,14b-六氢-7-甲基-4,8-甲桥苯并呋喃并(2,3-a)吡啶并(4,3-b)咔唑-1,8a(9H)-二醇 | 111469-88-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 中文名称: (4bS,8R,8aS,14bR)-5,6,7,8,14,14b-六氢-7-甲基-4,8-甲桥苯并呋喃并(2,3-a)吡啶并(4,3-b)咔唑-1,8a(9H)-二醇
• 英文名称: Oxymorphindole
• 英文别名: (1S,2S,13R,21R)-22-methyl-14-oxa-11,22-diazaheptacyclo[13.9.1.01,13.02,21.04,12.05,10.019,25]pentacosa-4(12),5,7,9,15,17,19(25)-heptaene-2,16-diol
• CAS: 111469-88-6
• 化学式: C₂₃H₂₂N₂O₃
• 分子量: 374.439
• InChiKey: YQNZUKAKYJMEFE-LMDOGRNLSA-N

物化性质

• 沸点：
  612.2±55.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  68.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4bS,8R,8aS,14bR)-5,6,7,8,14,14b-六氢-7-甲基-4,8-甲桥苯并呋喃并(2,3-a)吡啶并(4,3-b)咔唑-1,8a(9H)-二醇 在 4-二甲氨基吡啶 、 TEA 、 sodium hydride 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1S,2S,13R,21R)-11-(2-fluoroethyl)-22-methyl-14-oxa-11,22-diazaheptacyclo[13.9.1.01,13.02,21.04,12.05,10.019,25]pentacosa-4(12),5,7,9,15,17,19(25)-heptaene-2,16-diol
  参考文献：
  名称：

  Selective δ-opioid receptor ligands: potential PET ligands based on naltrindole

  摘要：

  Two series of delta -selective ligands related to the prototypic delta -antagonist naltrindole have been prepared and evaluated in opioid binding assays with the aim of developing new PET ligands for the delta -opioid receptor. One compound (5d) had significantly here selectivity than naltrindole, but with substantially reduced binding affinity. For those compounds retaining similar affinity to naltrindole. those having ethyl and fluoroethyl substituents afforded the highest levels of selectivity. However, none of the compounds combined the high level of affinity and selectivity ideally suited to the development of an imaging agent. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00112-3
• 作为产物：
  描述：

  oxycodindole 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以69%的产率得到(4bS,8R,8aS,14bR)-5,6,7,8,14,14b-六氢-7-甲基-4,8-甲桥苯并呋喃并(2,3-a)吡啶并(4,3-b)咔唑-1,8a(9H)-二醇
  参考文献：
  名称：

  L-Selectride as a General Reagent for the O-Demethylation and N-Decarbomethoxylation of Opium Alkaloids and Derivatives¹

  摘要：

  L-Selectride was shown to be an efficient and general O-demethylating agent for the opium alkaloids and their derivatives and also an efficient reagent for the cleavage of methyl carbamates, thus offering a convenient method for the N-demethylation of opioids. Further, it was shown that by choice of reaction conditions it is possible to achieve both N-decarbomethoxylation and O-demethylation in one pot, or only render N-decarbomethoxylation in high yield without accompanying O-demethylation.

  DOI：

  10.1021/jo9801972

文献信息

• Application of the message-address concept in the design of highly potent and selective non-peptide .delta. opioid receptor antagonists
  作者：P. S. Portoghese、M. Sultana、H. Nagase、A. E. Takemori

  DOI：10.1021/jm00397a001

  日期：1988.2
• WO2024006977A1
  申请人：——

  公开号：——

  公开（公告）日：——
• L-Selectride as a General Reagent for the O-Demethylation and N-Decarbomethoxylation of Opium Alkaloids and Derivatives¹
  作者：Andrew Coop、James W. Janetka、John W. Lewis、Kenner C. Rice

  DOI：10.1021/jo9801972

  日期：1998.6.1

  L-Selectride was shown to be an efficient and general O-demethylating agent for the opium alkaloids and their derivatives and also an efficient reagent for the cleavage of methyl carbamates, thus offering a convenient method for the N-demethylation of opioids. Further, it was shown that by choice of reaction conditions it is possible to achieve both N-decarbomethoxylation and O-demethylation in one pot, or only render N-decarbomethoxylation in high yield without accompanying O-demethylation.
• Selective δ-opioid receptor ligands: potential PET ligands based on naltrindole
  作者：Joanne Clayson、Andrew Jales、Robin J Tyacke、Alan L Hudson、David J Nutt、John W Lewis、Stephen M Husbands

  DOI：10.1016/s0960-894x(01)00112-3

  日期：2001.4

  Two series of delta -selective ligands related to the prototypic delta -antagonist naltrindole have been prepared and evaluated in opioid binding assays with the aim of developing new PET ligands for the delta -opioid receptor. One compound (5d) had significantly here selectivity than naltrindole, but with substantially reduced binding affinity. For those compounds retaining similar affinity to naltrindole. those having ethyl and fluoroethyl substituents afforded the highest levels of selectivity. However, none of the compounds combined the high level of affinity and selectivity ideally suited to the development of an imaging agent. (C) 2001 Elsevier Science Ltd. All rights reserved.