rac-(6Ξ)-6,14-epoxy-17-methyl-7,8-seco-morphinan-3-ol

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - Oxamorphinans
• 英文名称: rac-(6Ξ)-6,14-epoxy-17-methyl-7,8-seco-morphinan-3-ol
• 英文别名: (1R,9R,10S)-10,12,16-trimethyl-11-oxa-16-azatetracyclo[7.4.3.01,10.02,7]hexadeca-2(7),3,5-trien-4-ol
• 化学式: C₁₇H₂₃NO₂
• 分子量: 273.375
• InChiKey: KOIWWLNSZWPHPI-OMILXILMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  rac-3-methoxy-17-methyl-7,8-seco-morphin-6-en-14-ol 在 氢溴酸 作用下， 反应 0.17h， 生成 rac-(6Ξ)-6,14-epoxy-17-methyl-7,8-seco-morphinan-3-ol
  参考文献：
  名称：

  5-Allyl-9-oxobenzomorphans. 3. Potent narcotic antagonists and analgesics-antagonists in the series of substituted 2',9.beta.-dihydroxy-6,7-benzomorphans

  摘要：

  5-Allyl-2'-methoxy-2-methyl-9-oxo-6,7-benzomorphan methiodide (1) has been converted in a selective two-step process to the corresponding 9beta-hydroxy intermediates 4 and 6, which in turn were transformed via modified von Braun demethylation-acylation to the amides 11 and 21, respectively. These were reduced and demethylated to give a series of 5-allyl-2',9beta-dihydroxy-2-substituted 6,7-benzomorphans 13 and 23, some of which have been found to be highly potent narcotic antagonists and/or analgesics. The resolution of the most interesting compounds (23a and 23b) and pharmacological properties of the optical isomers are also described. Reduction of the double bond in 13 and 23 to give 14 and 24, with one exception, did not appreciably alter pharmacological profiles, while cyclization to the tetrahydrofuranobenzomorphans 25 substantially reduced the level of activities.

  DOI：

  10.1021/jm00215a012

文献信息

• 5-Allyl-9-oxobenzomorphans. 3. Potent narcotic antagonists and analgesics-antagonists in the series of substituted 2',9.beta.-dihydroxy-6,7-benzomorphans
  作者：Michel Saucier、Jean Paul Daris、Yvon Lambert、Ivo Monkovic、Anthony W. Pircio

  DOI：10.1021/jm00215a012

  日期：1977.5

  5-Allyl-2'-methoxy-2-methyl-9-oxo-6,7-benzomorphan methiodide (1) has been converted in a selective two-step process to the corresponding 9beta-hydroxy intermediates 4 and 6, which in turn were transformed via modified von Braun demethylation-acylation to the amides 11 and 21, respectively. These were reduced and demethylated to give a series of 5-allyl-2',9beta-dihydroxy-2-substituted 6,7-benzomorphans 13 and 23, some of which have been found to be highly potent narcotic antagonists and/or analgesics. The resolution of the most interesting compounds (23a and 23b) and pharmacological properties of the optical isomers are also described. Reduction of the double bond in 13 and 23 to give 14 and 24, with one exception, did not appreciably alter pharmacological profiles, while cyclization to the tetrahydrofuranobenzomorphans 25 substantially reduced the level of activities.