(R)-2-((4bS,8aS,9S)-3-((3-fluorobenzyl)oxy)-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthren-11-yl)propanoic acid | 214326-05-3

• 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: (R)-2-((4bS,8aS,9S)-3-((3-fluorobenzyl)oxy)-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthren-11-yl)propanoic acid
• CAS: 214326-05-3
• 化学式: C₂₆H₃₀FNO₃
• 分子量: 423.528
• InChiKey: COWIQNVXHPUKAB-MPIYNKIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-2-((4bS,8aS,9S)-3-((3-fluorobenzyl)oxy)-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthren-11-yl)propanoic acid 在 氨 、 三乙胺 作用下， 以 氯仿 为溶剂， 生成 (2R)-2-[(1S,9S,10S)-4-[(3-fluorophenyl)methoxy]-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-17-yl]propanamide
  参考文献：
  名称：

  Synthesis and preliminary biological evaluation of new α-amino amide anticonvulsants incorporating a dextromethorphan moiety

  摘要：

  Dextromethorphan 1 is an effective neuroprotectant in animal models of epilepsy and ischemia but showed side-effects during clinical trials limiting its potential use in a clinical setting. Here we describe the enantioselective and enantiospecific syntheses and the initial in vitro and in vivo biological evaluation of new hybrid structures between 1 and a previously disclosed alpha-amino amide anticonvulsant (3). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00271-1
• 作为产物：
  描述：

  右美沙芬 在 sodium hydroxide 、 三溴化硼 、 potassium carbonate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 锌 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 (R)-2-((4bS,8aS,9S)-3-((3-fluorobenzyl)oxy)-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthren-11-yl)propanoic acid
  参考文献：
  名称：

  Synthesis and preliminary biological evaluation of new α-amino amide anticonvulsants incorporating a dextromethorphan moiety

  摘要：

  Dextromethorphan 1 is an effective neuroprotectant in animal models of epilepsy and ischemia but showed side-effects during clinical trials limiting its potential use in a clinical setting. Here we describe the enantioselective and enantiospecific syntheses and the initial in vitro and in vivo biological evaluation of new hybrid structures between 1 and a previously disclosed alpha-amino amide anticonvulsant (3). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00271-1