7α-(1-hydroxy-1-methylethyl)-6-(cyclopropylmethoxy)-6-demethoxy-6,7,8,14-tetrahydro-6,14-endo-ethenothebaine | 1228362-68-2

• 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-(1-hydroxy-1-methylethyl)-6-(cyclopropylmethoxy)-6-demethoxy-6,7,8,14-tetrahydro-6,14-endo-ethenothebaine
• CAS: 1228362-68-2
• 化学式: C₂₇H₃₅NO₄
• 分子量: 437.579
• InChiKey: XBRWPQQUIFDDTE-JZGHPPSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  51.16
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  7α-(1-hydroxy-1-methylethyl)-6-(cyclopropylmethoxy)-6-demethoxy-6,7,8,14-tetrahydro-6,14-endo-ethenothebaine 在 水 、 potassium hydroxide 作用下， 以 乙二醇 为溶剂， 反应 8.0h， 以61%的产率得到7α-(1-hydroxy-1-methylethyl)-6-(cyclopropylmethoxy)-6-demethoxy-6,7,8,14-tetrahydro-6,14-endo-ethenooripavine
  参考文献：
  名称：

  Synthesis and opioid activity of novel 6-substituted-6-demethoxy-ethenomorphinans

  摘要：

  A set of novel 6-substituted orvinols was synthesized and pharmacologically characterized in order to explore the effect of the polarity and steric effects of these new moieties on the opioid activity. It was revealed that longer 6-O-alkyl chains led to increased agonistic activities, while the lack of C6-etheral oxygen gave rise to an antagonistic profile at the opioid receptors in the mouse ileum. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.068
• 作为产物：
  描述：

  溴甲烷 、 7α-acetyl-6-(cyclopropylmethoxy)-6-demethoxy-6,7,8,14-tetrahydro-6,14-endo-ethenothebaine 在 magnesium 、 水 、 氯化铵 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 以75%的产率得到7α-(1-hydroxy-1-methylethyl)-6-(cyclopropylmethoxy)-6-demethoxy-6,7,8,14-tetrahydro-6,14-endo-ethenothebaine
  参考文献：
  名称：

  Synthesis and opioid activity of novel 6-substituted-6-demethoxy-ethenomorphinans

  摘要：

  A set of novel 6-substituted orvinols was synthesized and pharmacologically characterized in order to explore the effect of the polarity and steric effects of these new moieties on the opioid activity. It was revealed that longer 6-O-alkyl chains led to increased agonistic activities, while the lack of C6-etheral oxygen gave rise to an antagonistic profile at the opioid receptors in the mouse ileum. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.068