7α-<(1R)-1-hydroxy-1-methyl-3-<4-(allyloxy)phenyl>propyl>-6,14-endo-ethenotetrahydronorthebaine | 98704-52-0

• 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: 7α-<(1R)-1-hydroxy-1-methyl-3-<4-(allyloxy)phenyl>propyl>-6,14-endo-ethenotetrahydronorthebaine
• 英文别名: 7α-{(1R)-1-hydroxy-1-methyl-3-[4-(allyloxy)phenyl]propyl}-6,14-endo-ethenotetrahydronorthebaine
• CAS: 98704-52-0
• 化学式: C₃₃H₃₉NO₅
• 分子量: 529.676
• InChiKey: WMCIKFKPZFBPAO-GIZYTINFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  39.0
• 可旋转键数：
  9.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  69.18
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  溴甲基环丙烷 、 7α-<(1R)-1-hydroxy-1-methyl-3-<4-(allyloxy)phenyl>propyl>-6,14-endo-ethenotetrahydronorthebaine 在 sodium carbonate 、 sodium iodide 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 以77%的产率得到7α-<(1R)-1-hydroxy-1-methyl-3-<4-(allyloxy)phenyl>propyl>-6,14-endo-ethenotetrahydro-N-(cyclopropylmethyl)northebaine
  参考文献：
  名称：

  Hybromet: a ligand for purifying opioid receptors

  摘要：

  Condensation of the Grignard reagent derive from 2-[4-(allyloxy)phenyl]ethyl bromide (4b) with 7 alpha-acetyl-6,14-endo-ethenotetrahydrothebaine (5) furnished the (R) tertiary carbinol, 7, which upon methoxymercuration followed by treatment with the KBr gave the bromomercurio compound 10 (Hybromet). The corresponding N-cyclopropylmethyl analogue, 11, was prepared also. The bromomercurio compound, 1, and the mercaptobenzothiazole derivative, 3, gave allyl phenyl ether when treated with BAL at room temperature. Similar treatment of 10 with BAL gave 7 in high yield. Binding studies using rat brain homogenates indicated that 7, 13, and 14 have moderately high affinities for mu rather than delta binding sites. Although much weaker, 10 showed preferential mu binding also. These results along with the fact that 10 reacted smoothly with sulfhydryl groups suggest that Hybromet would be a suitable ligand for use in affinity chromatography.

  DOI：

  10.1021/jm00150a032
• 作为产物：
  描述：

  在 ethyl azodicarboxylate 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 7α-<(1R)-1-hydroxy-1-methyl-3-<4-(allyloxy)phenyl>propyl>-6,14-endo-ethenotetrahydronorthebaine
  参考文献：
  名称：

  Hybromet: a ligand for purifying opioid receptors

  摘要：

  Condensation of the Grignard reagent derive from 2-[4-(allyloxy)phenyl]ethyl bromide (4b) with 7 alpha-acetyl-6,14-endo-ethenotetrahydrothebaine (5) furnished the (R) tertiary carbinol, 7, which upon methoxymercuration followed by treatment with the KBr gave the bromomercurio compound 10 (Hybromet). The corresponding N-cyclopropylmethyl analogue, 11, was prepared also. The bromomercurio compound, 1, and the mercaptobenzothiazole derivative, 3, gave allyl phenyl ether when treated with BAL at room temperature. Similar treatment of 10 with BAL gave 7 in high yield. Binding studies using rat brain homogenates indicated that 7, 13, and 14 have moderately high affinities for mu rather than delta binding sites. Although much weaker, 10 showed preferential mu binding also. These results along with the fact that 10 reacted smoothly with sulfhydryl groups suggest that Hybromet would be a suitable ligand for use in affinity chromatography.

  DOI：

  10.1021/jm00150a032