4,5α-epoxy-17-methylmorphinan-6-spiro-2'-(1',3'-dioxolane) | 32295-30-0

• 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: 4,5α-epoxy-17-methylmorphinan-6-spiro-2'-(1',3'-dioxolane)
• 英文别名: Morphinan-6-one, 4,5-epoxy-17-methyl-, cyclic 1,2-ethanediyl acetal, (5I+/-)-；(4R,4aR,7aR,12bS)-3-methylspiro[1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7,2'-1,3-dioxolane]
• CAS: 32295-30-0
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: ZPQVYTJUTDKFJI-JFTQMJAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  30.93
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4,5α-epoxy-17-methylmorphinan-6-spiro-2'-(1',3'-dioxolane) 在 盐酸 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 1.0h， 以81%的产率得到4,5-epoxy-17-methylmorphinan-6-one
  参考文献：
  名称：

  Synthesis of quinolinomorphinan-4-ol derivatives as δ opioid receptor agonists

  摘要：

  The previously reported morphinan derivative SN-28 showed high selectivity and agonist activity for the delta opioid receptor. In the course of examining the structure-activity relationship of SN-28 derivatives, the derivatives with the 4-hydroxy group (SN-24, 26, 27) showed higher selectivities for the 8 receptor over the mu receptor than the corresponding SN-28 derivatives with the 3-hydroxy group (SN-11, 23, 28). Derivatives with the 4-hydroxy group showed potent agonist activities for the 5 receptor in the [S-35]GTPyS binding assay. Although the 17-cyclopropylmethyl derivative (SN-11) with a 3-hydroxy group showed the lowest selectivity for the delta receptor among the morphinan derivatives, the agonist activity toward the delta receptor was the most potent for candidates with the 3-hydroxy group. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.047
• 作为产物：
  描述：

  3-desoxynaltrexone 在 吡啶 、 platinum(IV) oxide 、 lithium aluminium tetrahydride 、 氯化亚砜 、 氢气 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 、 1,1,2,2-四氯乙烷 为溶剂， 反应 37.0h， 生成 4,5α-epoxy-17-methylmorphinan-6-spiro-2'-(1',3'-dioxolane)
  参考文献：
  名称：

  Synthesis of quinolinomorphinan-4-ol derivatives as δ opioid receptor agonists

  摘要：

  The previously reported morphinan derivative SN-28 showed high selectivity and agonist activity for the delta opioid receptor. In the course of examining the structure-activity relationship of SN-28 derivatives, the derivatives with the 4-hydroxy group (SN-24, 26, 27) showed higher selectivities for the 8 receptor over the mu receptor than the corresponding SN-28 derivatives with the 3-hydroxy group (SN-11, 23, 28). Derivatives with the 4-hydroxy group showed potent agonist activities for the 5 receptor in the [S-35]GTPyS binding assay. Although the 17-cyclopropylmethyl derivative (SN-11) with a 3-hydroxy group showed the lowest selectivity for the delta receptor among the morphinan derivatives, the agonist activity toward the delta receptor was the most potent for candidates with the 3-hydroxy group. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.047