3-(1-methylpiperidin-4-yl)phenol hydrochloride | 105788-12-3

• 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: 3-(1-methylpiperidin-4-yl)phenol hydrochloride
• 英文别名: 3-(1-methyl-[4]piperidyl)-phenol; hydrochloride；3-(1-Methyl-4-piperidinyl)phenol hydrochloride；3-(1-methylpiperidin-4-yl)phenol;hydrochloride
• CAS: 105788-12-3
• 化学式: C₁₂H₁₇NO*ClH
• 分子量: 227.734
• InChiKey: BKWSDVYMIKFHTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  23.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(1-methylpiperidin-4-yl)phenol 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 3-(1-methylpiperidin-4-yl)phenol hydrochloride
  参考文献：
  名称：

  Effect of the 3- and 4-Methyl Groups on the Opioid Receptor Properties of N-Substituted trans-3,4-Dimethyl-4-(3-hydroxyphenyl)piperidines

  摘要：

  N-substituted trans-3,4-dimethy1-4-(3-hydroxyphenyOpiperidines (2a,b) are opioid receptor antagonists where the antagonist properties are not due to the type of N-substituent. In order to gain a better understanding of the contribution that the 3- and 4-methyl groups make to the pure antagonist properties of 2a,b, we synthesized analogues of 2a,b that lacked the 4-methyl (5a,b), 3-methyl (6a,b), and both the 3- and 4-methyl group (7a,b) and compared their opioid receptor properties. We found that (1) all N-methyl and N-phenylpropyl substituted compounds were nonselective opioid antagonists (2) all N-phenylpropyl analogues were more potent than their N-methyl counterparts, and (3) compounds 2a,b which have both a 3- and 4-methyl substituent, were more potent antagonists than analogues 5a,b, 6a,b, and 7a,b. We also found that the removal of 3-methyl substituent of N-methyl and N-phenylpropyl 3-methyl-4-(3-hydroxyphenyl)piperazines (8a,b) gives (4a,b), which are opioid antagonists.

  DOI：

  10.1021/jm500184j

文献信息

• Effect of the 3- and 4-Methyl Groups on the Opioid Receptor Properties of N-Substituted <i>trans</i>-3,4-Dimethyl-4-(3-hydroxyphenyl)piperidines
  作者：Chad M. Kormos、Juan Pablo Cueva、Moses G. Gichinga、Scott P. Runyon、James B. Thomas、Lawrence E. Brieaddy、S. Wayne Mascarella、Brian P. Gilmour、Hernán A. Navarro、F. Ivy Carroll

  DOI：10.1021/jm500184j

  日期：2014.4.10

  N-substituted trans-3,4-dimethy1-4-(3-hydroxyphenyOpiperidines (2a,b) are opioid receptor antagonists where the antagonist properties are not due to the type of N-substituent. In order to gain a better understanding of the contribution that the 3- and 4-methyl groups make to the pure antagonist properties of 2a,b, we synthesized analogues of 2a,b that lacked the 4-methyl (5a,b), 3-methyl (6a,b), and both the 3- and 4-methyl group (7a,b) and compared their opioid receptor properties. We found that (1) all N-methyl and N-phenylpropyl substituted compounds were nonselective opioid antagonists (2) all N-phenylpropyl analogues were more potent than their N-methyl counterparts, and (3) compounds 2a,b which have both a 3- and 4-methyl substituent, were more potent antagonists than analogues 5a,b, 6a,b, and 7a,b. We also found that the removal of 3-methyl substituent of N-methyl and N-phenylpropyl 3-methyl-4-(3-hydroxyphenyl)piperazines (8a,b) gives (4a,b), which are opioid antagonists.