3-[3,4-二甲基-1-(2-苯基乙基)哌啶-4-基]苯酚 | 82970-72-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 3-[3,4-二甲基-1-(2-苯基乙基)哌啶-4-基]苯酚
• 英文名称: (+/-)-1-(2-phenylethyl)-3(R^*),4(R^*)-dimethyl-4-(3-hydroxyphenyl)piperidine
• 英文别名: 3-(3,4-Dimethyl-1-phenethyl-piperidin-4-yl)-phenol；3-[(3R,4R)-3,4-dimethyl-1-(2-phenylethyl)piperidin-4-yl]phenol
• CAS: 82970-72-7
• 化学式: C₂₁H₂₇NO
• 分子量: 309.451
• InChiKey: ULOGPOOAAOSAOC-LAUBAEHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[3,4-二甲基-1-(2-苯基乙基)哌啶-4-基]苯酚 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 3-((3R,4R)-3,4-二甲基-1-苯乙基-哌啶-4-基)-苯甲酸甲酯
  参考文献：
  名称：

  反式3,4-二甲基-4-（3-羧酰胺基苯基）哌啶：一类新型的微选择阿片类拮抗剂。

  摘要：

  反式-3,4-二甲基-4-（3-羧酰胺基苯基）哌啶构成了一类新型的微阿片受体拮抗剂。发现CONH（2）组是酚OH部分的有效等排体。在哌啶氮位置的结构活性关系导致鉴定了几个配体，这些配体对克隆的人微阿片样物质受体具有高亲和力，良好的选择性micro / delta，micro / kappa和有效的体外拮抗剂活性。

  DOI：

  10.1016/j.bmcl.2003.09.012
• 作为产物：
  描述：

  1,4,5,6-Tetrahydro-4-(3-methoxyphenyl)-N,N,1,4-tetramethyl-3-pyridinemethanamine 在 platinum on activated charcoal 盐酸 、 Proton Sponge 、 氯甲酸乙烯酯 、 氢溴酸 、 氢气 、 碳酸氢钠 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 3-[3,4-二甲基-1-(2-苯基乙基)哌啶-4-基]苯酚
  参考文献：
  名称：

  Structure-activity relationships of trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine antagonists for .mu.- and .kappa.-opioid receptors

  摘要：

  A series of racemic N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines were evaluated for opioid agonist and antagonist activity at mu and kappa receptors. Several highly potent mu and kappa antagonists were discovered; however, no compounds with high selectivity for either the mu or kappa receptor were identified. Importantly, no derivative was found to have significant opioid agonist activity. Two derivatives were resolved, and the activities of the enantiomers were investigated. Only a limited stereochemical effect on opioid receptor selectivities was observed. The structure-activity relationships described establish the existence of an important lipophilic binding site distal to the nitrogen for both mu and kappa receptors and confirm the pure opioid antagonist pharmacophore nature of the trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine structure.

  DOI：

  10.1021/jm00072a001

文献信息

• trans -3,4-Dimethyl-4-(3-carboxamidophenyl)piperidines: A novel class of μ-Selective opioid antagonists
  作者：Bertrand Le Bourdonnec、Serge Belanger、Joel A. Cassel、Gabriel J. Stabley、Robert N. DeHaven、Roland E. Dolle

  DOI：10.1016/j.bmcl.2003.09.012

  日期：2003.12

  trans-3,4-Dimethyl-4-(3-carboxamidophenyl)piperidines constitute a novel class of micro opioid receptor antagonists. The CONH(2) group was found to be an effective isostere of the phenolic OH moiety. Structure-activity relationships at the piperidine nitrogen position led to the identification of several ligands displaying high affinity toward the cloned human micro opioid receptors, good selectivity

  反式-3,4-二甲基-4-（3-羧酰胺基苯基）哌啶构成了一类新型的微阿片受体拮抗剂。发现CONH（2）组是酚OH部分的有效等排体。在哌啶氮位置的结构活性关系导致鉴定了几个配体，这些配体对克隆的人微阿片样物质受体具有高亲和力，良好的选择性micro / delta，micro / kappa和有效的体外拮抗剂活性。
• Structure-activity relationships of trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine antagonists for .mu.- and .kappa.-opioid receptors
  作者：Dennis M. Zimmerman、J. David Leander、Buddy E. Cantrell、Jon K. Reel、John Snoddy、Laurane G. Mendelsohn、Bryan G. Johnson、Charles H. Mitch

  DOI：10.1021/jm00072a001

  日期：1993.10

  A series of racemic N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines were evaluated for opioid agonist and antagonist activity at mu and kappa receptors. Several highly potent mu and kappa antagonists were discovered; however, no compounds with high selectivity for either the mu or kappa receptor were identified. Importantly, no derivative was found to have significant opioid agonist activity. Two derivatives were resolved, and the activities of the enantiomers were investigated. Only a limited stereochemical effect on opioid receptor selectivities was observed. The structure-activity relationships described establish the existence of an important lipophilic binding site distal to the nitrogen for both mu and kappa receptors and confirm the pure opioid antagonist pharmacophore nature of the trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine structure.