14-benzyloxy-17-cyclopropylmethyl-4,5α-epoxymorphinan-6-spiro-2'-dioxolane | 220556-51-4

• 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: 14-benzyloxy-17-cyclopropylmethyl-4,5α-epoxymorphinan-6-spiro-2'-dioxolane
• 英文别名: (4'R,4'aS,7'aR,12'bS)-3'-(cyclopropylmethyl)-4'a-phenylmethoxyspiro[1,3-dioxolane-2,7'-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline]
• CAS: 220556-51-4
• 化学式: C₂₉H₃₃NO₄
• 分子量: 459.585
• InChiKey: NQQIKSLLKHTHSE-AOGFTHLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  40.16
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  14-benzyloxy-17-cyclopropylmethyl-4,5α-epoxymorphinan-6-spiro-2'-dioxolane 在 盐酸 、 氯化铵 、 锌 作用下， 以 甲醇 、 水 为溶剂， 反应 5.5h， 生成 14-benzyloxy-17-cyclopropylmethyl-4-hydroxymorphinan-6-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 14-Alkoxymorphinans. 16. 14-O-Alkyl Derivatives of the m-Opioid Receptor Antagonist Cyprodime

  摘要：

  The 14-O-benzyl derivatives of cyprodime and 3-hydroxycyprodime (compounds (5) and (6), respectively) were synthesized in several steps from 3-desoxynaltrexone (2a) and naltrexone (2), respectively. In the mouse vas deferens preparation it was found that a 14-O-benzyl group could enhance mu opioid receptor affinity in cyprodime while the mu affinity of 3-hydroxycyprodime was not changed.

  DOI：

  10.3987/com-98-s60
• 作为产物：
  描述：

  3-desoxynaltrexone 在 甲烷磺酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 Petroleum ether 为溶剂， 反应 18.0h， 生成 14-benzyloxy-17-cyclopropylmethyl-4,5α-epoxymorphinan-6-spiro-2'-dioxolane
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 14-Alkoxymorphinans. 16. 14-O-Alkyl Derivatives of the m-Opioid Receptor Antagonist Cyprodime

  摘要：

  The 14-O-benzyl derivatives of cyprodime and 3-hydroxycyprodime (compounds (5) and (6), respectively) were synthesized in several steps from 3-desoxynaltrexone (2a) and naltrexone (2), respectively. In the mouse vas deferens preparation it was found that a 14-O-benzyl group could enhance mu opioid receptor affinity in cyprodime while the mu affinity of 3-hydroxycyprodime was not changed.

  DOI：

  10.3987/com-98-s60