6α-hydroxymethyl-3-methoxy-17-methylmorphinan-4,14β-diol | 1033438-81-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 6α-hydroxymethyl-3-methoxy-17-methylmorphinan-4,14β-diol
• CAS: 1033438-81-1
• 化学式: C₁₉H₂₇NO₄
• 分子量: 333.428
• InChiKey: VRMXGFDIEGWHIP-GGCQVYRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.42
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  73.16
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6α-hydroxymethyl-3-methoxy-17-methylmorphinan-4,14β-diol 、 甲基磺酰氯 以 吡啶 为溶剂， 反应 3.0h， 生成 6α-methanesulfonyloxymethyl-3-methoxy-17-methylmorphinan-4,14β-diol
  参考文献：
  名称：

  Syntheses of 4,6′-epoxymorphinan derivatives and their pharmacologies

  摘要：

  A modi. cation of the message site in the skeleton of naltrexone was carried out to improve the potency and selectivity of the compound for an opioid receptor subtype. In the course of conversion, we synthesized 7-membered ring ether derivatives, which had an inserted OCH2 group between 4- and 6-positions of morphinan skeleton. One of the 7-membered ring ether derivatives possessed more potent antagonistic activity than naltrexone for the l opioid receptor. Another compound possessing 17-methyl group derived from noroxycodone may be a l opioid receptor partial agonist and showed analgesic activity. We are currently examining the subtype selectivity of these compounds. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.082
• 作为产物：
  描述：

  4,14β-dihydroxy-3-methoxy-17-methylmorphinan-6α-calbaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以60%的产率得到6α-hydroxymethyl-3-methoxy-17-methylmorphinan-4,14β-diol
  参考文献：
  名称：

  Syntheses of 4,6′-epoxymorphinan derivatives and their pharmacologies

  摘要：

  A modi. cation of the message site in the skeleton of naltrexone was carried out to improve the potency and selectivity of the compound for an opioid receptor subtype. In the course of conversion, we synthesized 7-membered ring ether derivatives, which had an inserted OCH2 group between 4- and 6-positions of morphinan skeleton. One of the 7-membered ring ether derivatives possessed more potent antagonistic activity than naltrexone for the l opioid receptor. Another compound possessing 17-methyl group derived from noroxycodone may be a l opioid receptor partial agonist and showed analgesic activity. We are currently examining the subtype selectivity of these compounds. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.082