2-Methoxy-1-(4-methoxy-benzyl)-5-methyl-cyclohexa-2,5-dienecarboxylic acid methyl ester | 176959-92-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-Methoxy-1-(4-methoxy-benzyl)-5-methyl-cyclohexa-2,5-dienecarboxylic acid methyl ester
• 英文别名: Methyl 2-methoxy-1-[(4-methoxyphenyl)methyl]-5-methylcyclohexa-2,5-diene-1-carboxylate
• CAS: 176959-92-5
• 化学式: C₁₈H₂₂O₄
• 分子量: 302.37
• InChiKey: XUCIMOMGZHDMJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Methoxy-1-(4-methoxy-benzyl)-5-methyl-cyclohexa-2,5-dienecarboxylic acid methyl ester 在 lithium aluminium tetrahydride 、 sodium azide 、 三氟甲磺酸 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 4.25h， 生成 5,10-methano-3-methoxy-10-(methoxymethyl)-5-methyl-5,6,7,9,10,11-hexahydrotetrazolo[1,2-i]-9-benzazonine
  参考文献：
  名称：

  Asymmetric Syntheses, Opioid Receptor Affinities, and Antinociceptive Effects of 8-Amino-5,9-methanobenzocyclooctenes, a New Class of Structural Analogues of the Morphine Alkaloids

  摘要：

  Several 8-amino-5,9-methanobenzocyclooctenes have been prepared by asymmetric organic synthesis techniques. Opioid receptor affinity studies have revealed the virtual absence of enantioselectivity for receptor binding, particularly at the mu-receptor, for the (+)-3a-f and the (-)-3a-f series. It is noteworthy that inversion of configuration at the nitrogen-bearing carbon atom [(5S,8S,9S)-8-amino-3-hydroxy-5,9-methano-9-(methoxymethyl)-5-methylbenzocyclooctene, (+)-3a vs (5S,8S,9R)-8-amino-3-hydroxy-5,9-methanoxymethyl)-5-methylbenzocyclooctene, (dl)-22] resulted in a >10-fold increase in kappa-receptor affinity. Antinociceptive studies demonstrated that (dl)-22 was a full kappa-agonist while (+)-3a and (-)-3a did not possess kappa-activity. Although both (dl)-22 and (+)-3a/(-)-3a had high affinity for the mu-receptor, these compounds did not act as high-affinity agonists or antagonists at this receptor.

  DOI：

  10.1021/jm950817g
• 作为产物：
  描述：

  2-甲氧基-5-甲基苯甲酸甲酯 、 4-甲氧基溴苄 在 间戊二烯 、 氨 、 lithium 、 叔丁醇 作用下， 生成 2-Methoxy-1-(4-methoxy-benzyl)-5-methyl-cyclohexa-2,5-dienecarboxylic acid methyl ester
  参考文献：
  名称：

  Asymmetric Syntheses, Opioid Receptor Affinities, and Antinociceptive Effects of 8-Amino-5,9-methanobenzocyclooctenes, a New Class of Structural Analogues of the Morphine Alkaloids

  摘要：

  Several 8-amino-5,9-methanobenzocyclooctenes have been prepared by asymmetric organic synthesis techniques. Opioid receptor affinity studies have revealed the virtual absence of enantioselectivity for receptor binding, particularly at the mu-receptor, for the (+)-3a-f and the (-)-3a-f series. It is noteworthy that inversion of configuration at the nitrogen-bearing carbon atom [(5S,8S,9S)-8-amino-3-hydroxy-5,9-methano-9-(methoxymethyl)-5-methylbenzocyclooctene, (+)-3a vs (5S,8S,9R)-8-amino-3-hydroxy-5,9-methanoxymethyl)-5-methylbenzocyclooctene, (dl)-22] resulted in a >10-fold increase in kappa-receptor affinity. Antinociceptive studies demonstrated that (dl)-22 was a full kappa-agonist while (+)-3a and (-)-3a did not possess kappa-activity. Although both (dl)-22 and (+)-3a/(-)-3a had high affinity for the mu-receptor, these compounds did not act as high-affinity agonists or antagonists at this receptor.

  DOI：

  10.1021/jm950817g