(4R,4aR,7R,7aR,12bS)-3-(cyclopropylmethyl)-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol | 142790-79-2

• 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)-3-(cyclopropylmethyl)-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol
• CAS: 142790-79-2
• 化学式: C₂₀H₂₅NO₃
• 分子量: 327.423
• InChiKey: IVIHXIDMGGURLL-ZLOUOWRTSA-N

物化性质

• 沸点：
  518.5±50.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  52.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-demethyl-N-cyclopropylmethyldihydrocodeine 在 氢氧化钾 、 三溴化硼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醇 、 氯仿 、 苯 为溶剂， 反应 2.17h， 生成 (4R,4aR,7R,7aR,12bS)-3-(cyclopropylmethyl)-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

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.