trans-1-benzyl-4-(dimethylamino)-4-phenylcyclohexanol | 1616501-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: trans-1-benzyl-4-(dimethylamino)-4-phenylcyclohexanol
• CAS: 1616501-68-8
• 化学式: C₂₁H₂₇NO
• 分子量: 309.451
• InChiKey: UXKFNWQITCAPCS-MEMLXQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  23.47
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  trans-1-benzyl-4-(dimethylamino)-4-phenylcyclohexanol 在 三甲基氯硅烷 作用下， 以 水 、 丁酮 为溶剂， 以92%的产率得到trans-1-benzyl-4-(dimethylamino)-4-phenylcyclohexanol hydrochloride
  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：

  1,4-环己二酮单乙二醇缩酮 在 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 trans-1-benzyl-4-(dimethylamino)-4-phenylcyclohexanol
  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