17-cyclopropylmethyl-4,5α-epoxymorphinan-6-spiro-2'-(1',3'-dioxolane) | 1000410-52-5

• 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: 17-cyclopropylmethyl-4,5α-epoxymorphinan-6-spiro-2'-(1',3'-dioxolane)
• CAS: 1000410-52-5
• 化学式: C₂₂H₂₇NO₃
• 分子量: 353.461
• InChiKey: KMEFMGYHSWPFKB-NLEAXPPASA-N

物化性质

• 沸点：
  501.4±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  17-cyclopropylmethyl-4,5α-epoxymorphinan-6-spiro-2'-(1',3'-dioxolane) 在 盐酸 、 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 1,1,2,2-四氯乙烷 为溶剂， 反应 5.0h， 生成 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 、 氯化亚砜 、 氢气 、 对甲苯磺酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 33.0h， 生成 17-cyclopropylmethyl-4,5α-epoxymorphinan-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