Benzoic acid (1R,4S,5R)-5-(3-isopropoxy-phenyl)-2,4-dimethyl-2-aza-bicyclo[3.3.1]non-7-yl ester | 444904-25-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: Benzoic acid (1R,4S,5R)-5-(3-isopropoxy-phenyl)-2,4-dimethyl-2-aza-bicyclo[3.3.1]non-7-yl ester
• CAS: 444904-25-0
• 化学式: C₂₆H₃₃NO₃
• 分子量: 407.553
• InChiKey: LBLWVLIDPLUVAG-HNPRQGKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (1R,4S,5R)-5-(3-isopropoxy-phenyl)-2,4-dimethyl-2-aza-bicyclo[3.3.1]non-7-yl ester 在 lithium hydroxide 、 三乙酰氧基硼氢化钠 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 26.5h， 生成 (-)-(1R,4S,5S)-5-[3-(1-methylethoxy)phenyl]-4-methyl-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]nonan-7-ol
  参考文献：
  名称：

  Discovery of an Opioid κ Receptor Selective Pure Antagonist from a Library of N-Substituted 4β-Methyl-5-(3-hydroxyphenyl)morphans

  摘要：

  A library of compounds biased toward opioid receptor antagonist activity was prepared by incorporating N-phenylpropyl-4p-methyl-5-(3-hydroxyphenyl)morphans as the core scaffold using simultaneous solution phase synthetic methodology. From this library, N-phenylpropyl-4beta-methyl-5-(3-hydroxyphenyl)-7alpha-[3-(1-piperidinyl)propanamido]morphan [(-)-3b] was identified as the first potent and selective k opioid receptor antagonist from the 5-phenylmorphan class of opioids.

  DOI：

  10.1021/jm020084h
• 作为产物：
  描述：

  (-)-(1R,4S,5S)-5-[3-(1-methylethoxy)phenyl]-2,4-dimethyl-2-azabicyclo[3.3.1]nonan-7-one 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 Benzoic acid (1R,4S,5R)-5-(3-isopropoxy-phenyl)-2,4-dimethyl-2-aza-bicyclo[3.3.1]non-7-yl ester
  参考文献：
  名称：

  Discovery of an Opioid κ Receptor Selective Pure Antagonist from a Library of N-Substituted 4β-Methyl-5-(3-hydroxyphenyl)morphans

  摘要：

  A library of compounds biased toward opioid receptor antagonist activity was prepared by incorporating N-phenylpropyl-4p-methyl-5-(3-hydroxyphenyl)morphans as the core scaffold using simultaneous solution phase synthetic methodology. From this library, N-phenylpropyl-4beta-methyl-5-(3-hydroxyphenyl)-7alpha-[3-(1-piperidinyl)propanamido]morphan [(-)-3b] was identified as the first potent and selective k opioid receptor antagonist from the 5-phenylmorphan class of opioids.

  DOI：

  10.1021/jm020084h