[(4R,4aS,7R,7aR,12bS)-7-(1,3-dioxoisoindol-2-yl)-4a-hydroxy-3-prop-2-enyl-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl] acetate | 160359-58-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: [(4R,4aS,7R,7aR,12bS)-7-(1,3-dioxoisoindol-2-yl)-4a-hydroxy-3-prop-2-enyl-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl] acetate
• CAS: 160359-58-0
• 化学式: C₂₉H₂₈N₂O₆
• 分子量: 500.551
• InChiKey: USYIAZVXOSWAKX-CMZTTYMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  96.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(4R,4aS,7R,7aR,12bS)-7-(1,3-dioxoisoindol-2-yl)-4a-hydroxy-3-prop-2-enyl-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl] acetate 在 一水合肼 作用下， 以 乙醇 为溶剂， 以44%的产率得到β-naloxamine
  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：

  邻苯二甲酸亚胺 、 [(4R,4aS,7S,7aR,12bS)-4a,7-dihydroxy-3-prop-2-enyl-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl] acetate 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 苯 为溶剂， 反应 1.0h， 以30%的产率得到[(4R,4aS,7R,7aR,12bS)-7-(1,3-dioxoisoindol-2-yl)-4a-hydroxy-3-prop-2-enyl-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl] acetate
  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