(4R,4aR,7R,7aR,12bS)-9-methoxy-3-propyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol | 142790-74-7

• 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: (4R,4aR,7R,7aR,12bS)-9-methoxy-3-propyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol
• CAS: 142790-74-7
• 化学式: C₂₀H₂₇NO₃
• 分子量: 329.439
• InChiKey: GGTKBBXGZSCVBN-VYCUNPCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,4aR,7R,7aR,12bS)-9-methoxy-3-propyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol 在 三溴化硼 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以53%的产率得到(4R,4aR,7R,7aR,12bS)-3-propyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol
  参考文献：
  名称：

  Stereoselective synthesis of β-naltrexol, β-naloxol β-naloxamine, β-naltrexamine and related compounds by the application of the mitsunobu reac

  摘要：

  As a continuation of our work, aimed at adopting the Mitsunobu reaction in the morphine series, a few representatives of dihydroisocodeines and dihydroisomorphines and their 14 beta-hydroxy analogues were prepared. p-Nitrobenzoic acid was used as carboxylic acid and the prepared esters were cleaved to obtain the title compounds. Using phthalimide as acidic component several new 6 beta-phthalimidodihydromorphine and dihydrocodeine derivatives and their 14 beta-hydroxy analogues have been synthesized. Cleavage of the phthalimido derivatives with hydrazine hydrate afforded the corresponding 6 beta-amino derivatives.

  DOI：

  10.1016/s0040-4020(01)85541-1
• 作为产物：
  描述：

  N-demethyl-N-propyl-dihydrocodeine 在 氢氧化钾 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醇 、 苯 为溶剂， 反应 1.17h， 生成 (4R,4aR,7R,7aR,12bS)-9-methoxy-3-propyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol
  参考文献：
  名称：

  Stereoselective synthesis of β-naltrexol, β-naloxol β-naloxamine, β-naltrexamine and related compounds by the application of the mitsunobu reac

  摘要：

  As a continuation of our work, aimed at adopting the Mitsunobu reaction in the morphine series, a few representatives of dihydroisocodeines and dihydroisomorphines and their 14 beta-hydroxy analogues were prepared. p-Nitrobenzoic acid was used as carboxylic acid and the prepared esters were cleaved to obtain the title compounds. Using phthalimide as acidic component several new 6 beta-phthalimidodihydromorphine and dihydrocodeine derivatives and their 14 beta-hydroxy analogues have been synthesized. Cleavage of the phthalimido derivatives with hydrazine hydrate afforded the corresponding 6 beta-amino derivatives.

  DOI：

  10.1016/s0040-4020(01)85541-1

文献信息

• Synthesis of N-Demethyl-N-Substituted Dihydroisomorphine and Dihydroisocodeine Derivatives⁺
  作者：Sándor Hosztafi、Csaba Simon、Sándor Makleit

  DOI：10.1080/00397919208020486

  日期：1992.6

  Several new N-demethyl-N-alkyl derivatives (1p, 1r, 1s, 1m, 1n and 1o) of dihydroisomorphine and dihydroisocodeine, and N-demethyl-N-cyclopropylmethylisocodeine (2g) have been prepared. The presented synthetic procedure allows a convenient access to a series of structurally related, stereochemically homogeneous substances for studies of the agonist/antagonist properties.