8-but-3-inyloxy-1,4-dioxaspiro[4.5]decane | 1565377-92-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-but-3-inyloxy-1,4-dioxaspiro[4.5]decane
• 英文别名: 8-But-3-ynoxy-1,4-dioxaspiro[4.5]decane
• CAS: 1565377-92-5
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: KPCXYMDSELJHLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-but-3-inyloxy-1,4-dioxaspiro[4.5]decane 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 水 、 丙酮 为溶剂， 反应 49.0h， 生成 4-(4-triethylsilanylbut-3-ynyloxy)cyclohexanone
  参考文献：
  名称：

  Discovery of Spiro[cyclohexane-dihydropyrano[3,4-b]indole]-amines as Potent NOP and Opioid Receptor Agonists

  摘要：

  We report the discovery of spiro[cyclohexane-pyrano[3,4-b]indole]-amines, as functional nociceptin/orphanin FQ peptide (NOP) and opioid receptor agonists with strong efficacy in preclinical models of acute and neuropathic pain. Utilizing 4-(dimethylamino)-4-phenylcyclo-hexanone 1 and tryptophol in an oxa-Pictet-Spengler reaction led to the formation of spiroether 2, representing a novel NOP and opioid peptide receptor agonistic chemotype. This finding initially stems from the systematic derivatization of 1, which resulted in alcohols 3-5, ethers 6 and 7, amines 8-10, 22-24, and 26-28, amides 11 and 25, and urea 12, many with low nanomolar binding affinities at the NOP and mu opioid peptide (MOP) receptors.

  DOI：

  10.1021/ml500116x
• 作为产物：
  描述：

  4-羟基环己酮 在 对甲苯磺酸 、 1,8-二氨基萘 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 116.0h， 生成 8-but-3-inyloxy-1,4-dioxaspiro[4.5]decane
  参考文献：
  名称：

  Discovery of Spiro[cyclohexane-dihydropyrano[3,4-b]indole]-amines as Potent NOP and Opioid Receptor Agonists

  摘要：

  We report the discovery of spiro[cyclohexane-pyrano[3,4-b]indole]-amines, as functional nociceptin/orphanin FQ peptide (NOP) and opioid receptor agonists with strong efficacy in preclinical models of acute and neuropathic pain. Utilizing 4-(dimethylamino)-4-phenylcyclo-hexanone 1 and tryptophol in an oxa-Pictet-Spengler reaction led to the formation of spiroether 2, representing a novel NOP and opioid peptide receptor agonistic chemotype. This finding initially stems from the systematic derivatization of 1, which resulted in alcohols 3-5, ethers 6 and 7, amines 8-10, 22-24, and 26-28, amides 11 and 25, and urea 12, many with low nanomolar binding affinities at the NOP and mu opioid peptide (MOP) receptors.

  DOI：

  10.1021/ml500116x