N-demethyl-N-phenylethyl-14-hydroxycodeinone | 32968-91-5

• 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: N-demethyl-N-phenylethyl-14-hydroxycodeinone
• 英文别名: 4,5α-epoxy-14-hydroxy-3-methoxy-17-phenethyl-morphin-7-en-6-one；(4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-3-(2-phenylethyl)-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
• CAS: 32968-91-5
• 化学式: C₂₅H₂₅NO₄
• 分子量: 403.478
• InChiKey: ZSGUQJSQTAFYND-AKAGGGOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-demethyl-N-phenylethyl-14-hydroxycodeinone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以50%的产率得到(4R,4aS,7S,7aR,12bS)-9-methoxy-3-(2-phenylethyl)-1,2,4,7,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7-diol
  参考文献：
  名称：

  Synthesis of N-Demethyl-N-Substituted-14-Hydroxycodeine and Morphine Derivatives⁺

  摘要：

  A fews representatives (1b-d) of a novel group of structurally related morphine-antagonist compounds have been prepared in stereochemically homogeneous form. The employed procedures involve O-demethylation either of the corresponding codeine derivatives 2b-d, or those of the N-alkylated analogues 2b,c, synthesized from N-demethylthebaine (7a) by means of N-alkylation and subsequent transformations of 7b,d, - compounds selected from the resulting functionalized thebaines 7b-e.

  DOI：

  10.1080/00397919208021649
• 作为产物：
  描述：

  14-hydroxycodeine diacatate 在 盐酸 、 ammonium hydroxide 、 甲酸 、 双氧水 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 N-demethyl-N-phenylethyl-14-hydroxycodeinone
  参考文献：
  名称：

  Synthesis of N-Demethyl-N-Substituted-14-Hydroxycodeine and Morphine Derivatives⁺

  摘要：

  A fews representatives (1b-d) of a novel group of structurally related morphine-antagonist compounds have been prepared in stereochemically homogeneous form. The employed procedures involve O-demethylation either of the corresponding codeine derivatives 2b-d, or those of the N-alkylated analogues 2b,c, synthesized from N-demethylthebaine (7a) by means of N-alkylation and subsequent transformations of 7b,d, - compounds selected from the resulting functionalized thebaines 7b-e.

  DOI：

  10.1080/00397919208021649

文献信息

• Seki,I., Chemical and pharmaceutical bulletin, 1970, vol. 18, p. 671 - 676
  作者：Seki,I.

  DOI：——

  日期：——
• Synthesis of N-Demethyl-N-Substituted-14-Hydroxycodeine and Morphine Derivatives⁺
  作者：Sándor Hosztafi、Csaba Simon、Sándor Makleit

  DOI：10.1080/00397919208021649

  日期：1992.9

  A fews representatives (1b-d) of a novel group of structurally related morphine-antagonist compounds have been prepared in stereochemically homogeneous form. The employed procedures involve O-demethylation either of the corresponding codeine derivatives 2b-d, or those of the N-alkylated analogues 2b,c, synthesized from N-demethylthebaine (7a) by means of N-alkylation and subsequent transformations of 7b,d, - compounds selected from the resulting functionalized thebaines 7b-e.