2,2,2-trichloroethyl (4bS,8aS,9S)-3-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate | 214326-07-5

• 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: 2,2,2-trichloroethyl (4bS,8aS,9S)-3-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate
• CAS: 214326-07-5
• 化学式: C₁₉H₂₂Cl₃NO₃
• 分子量: 418.748
• InChiKey: VHRMHBQPSRHELO-HFTRVMKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  26.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 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：

  2,2,2-trichloroethyl (4bS,8aS,9S)-3-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate 在 sodium hydroxide 、 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 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
• 作为产物：
  描述：

  右美沙芬 在 三溴化硼 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 2,2,2-trichloroethyl (4bS,8aS,9S)-3-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate
  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