N-(cyclopropylmethyl)-14β-bromonorcodeinone | 76404-89-2

• 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: N-(cyclopropylmethyl)-14β-bromonorcodeinone
• CAS: 76404-89-2
• 化学式: C₂₁H₂₂BrNO₃
• 分子量: 416.315
• InChiKey: RFGJEKYTXLXRJK-MBPVOVBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(cyclopropylmethyl)-14β-bromonorcodeinone 在 三溴化硼 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以38%的产率得到N-(cyclopropylmethyl)-14β-bromonormorphinone
  参考文献：
  名称：

  Some 14.beta.-substituted analogs of N-(cyclopropylmethyl)normorphine

  摘要：

  A series of N-(cyclopropylmethyl)-14 beta-substituted-normorphine analogues was synthesized and tested for opioid agonist and antagonist activity in the guinea pig ileum and mouse vas deferens preparations. The 14 beta-bromo compound proved to be a pure antagonist equal in potency to naloxone in the guinea pig ileum assay. In contrast to N-(cyclopropylmethyl)-14 beta-hydroxynormorphine which was a pure antagonist, the corresponding sulfur analogue was about equal to nalorphine in agonist and antagonist potency.

  DOI：

  10.1021/jm00134a018
• 作为产物：
  描述：

  N-(cyclopropylmethyl)northebaine 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 丙酮 为溶剂， 反应 0.17h， 以21%的产率得到N-(cyclopropylmethyl)-14β-bromonorcodeinone
  参考文献：
  名称：

  Some 14.beta.-substituted analogs of N-(cyclopropylmethyl)normorphine

  摘要：

  A series of N-(cyclopropylmethyl)-14 beta-substituted-normorphine analogues was synthesized and tested for opioid agonist and antagonist activity in the guinea pig ileum and mouse vas deferens preparations. The 14 beta-bromo compound proved to be a pure antagonist equal in potency to naloxone in the guinea pig ileum assay. In contrast to N-(cyclopropylmethyl)-14 beta-hydroxynormorphine which was a pure antagonist, the corresponding sulfur analogue was about equal to nalorphine in agonist and antagonist potency.

  DOI：

  10.1021/jm00134a018