(-)-11α-(2-cyanoethyl)-7-hydroxy-6α-(hydroxymethyl)-8-methoxy-3-methyl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine | 102977-05-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 6,7-苯并吗啡烷
• 英文名称: (-)-11α-(2-cyanoethyl)-7-hydroxy-6α-(hydroxymethyl)-8-methoxy-3-methyl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine
• CAS: 102977-05-9
• 化学式: C₁₈H₂₄N₂O₃
• 分子量: 316.4
• InChiKey: VKAFXCVBYJYYCX-IYOUNJFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  76.72
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (-)-11α-(2-cyanoethyl)-7-hydroxy-6α-(hydroxymethyl)-8-methoxy-3-methyl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine 在 lithium aluminium tetrahydride 、 硫酸 、 甲基三苯基碘化膦 、 三溴化硼 、 sodium cyanoborohydride 、 potassium carbonate 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 95.0h， 生成 8-phenethyl-11-propyl-7,8,9,10-tetrahydro-1H,6H-7,10a-methanobenzofuro[3,4-de]azocin-3-ol
  参考文献：
  名称：

  Preparation and analgesic activity of (-)-11.alpha.-substituted 1,2,3,4,5,6-hexahydro-6.alpha.,7-(methyleneoxy)-2,6-methano-3-benzazocines

  摘要：

  Dihydrocodeinone oxime (1) under Beckmann rearrangement conditions gave a product (2) that facilitated the preparation of (-)-11 alpha-substituted 1,2,3,4,5,6-hexahydro-6 alpha,7-(methyleneoxy)-2,6-methano-3-benzazocines, a hitherto little-examined series of morphine partial structures. Compounds 7a and 12 gave good levels of agonist antinociceptive activity. Masking of the 8-oxygen function, as in 6 and 8, dramatically reduced mouse hot-plate activity, as did its loss (9).

  DOI：

  10.1021/jm00160a022
• 作为产物：
  描述：

  二氢可待因酮 在 sodium tetrahydroborate 、 氯化亚砜 、 盐酸羟胺 、 水 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 (-)-11α-(2-cyanoethyl)-7-hydroxy-6α-(hydroxymethyl)-8-methoxy-3-methyl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine
  参考文献：
  名称：

  Preparation and analgesic activity of (-)-11.alpha.-substituted 1,2,3,4,5,6-hexahydro-6.alpha.,7-(methyleneoxy)-2,6-methano-3-benzazocines

  摘要：

  Dihydrocodeinone oxime (1) under Beckmann rearrangement conditions gave a product (2) that facilitated the preparation of (-)-11 alpha-substituted 1,2,3,4,5,6-hexahydro-6 alpha,7-(methyleneoxy)-2,6-methano-3-benzazocines, a hitherto little-examined series of morphine partial structures. Compounds 7a and 12 gave good levels of agonist antinociceptive activity. Masking of the 8-oxygen function, as in 6 and 8, dramatically reduced mouse hot-plate activity, as did its loss (9).

  DOI：

  10.1021/jm00160a022

文献信息

• Cittern, Peter A.; Kapoor, Vijay K.; Parfitt, Robert T., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 1039 - 1040
  作者：Cittern, Peter A.、Kapoor, Vijay K.、Parfitt, Robert T.

  DOI：——

  日期：——