Trifluoro-methanesulfonic acid 3-[(3R,4R)-1-((S)-3-cyclohexyl-3-hydroxy-propyl)-3,4-dimethyl-piperidin-4-yl]-phenyl ester | 862911-59-9

• 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: Trifluoro-methanesulfonic acid 3-[(3R,4R)-1-((S)-3-cyclohexyl-3-hydroxy-propyl)-3,4-dimethyl-piperidin-4-yl]-phenyl ester
• CAS: 862911-59-9
• 化学式: C₂₃H₃₄F₃NO₄S
• 分子量: 477.588
• InChiKey: CADMDEXYPQNJIH-BULFRSBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid 3-[(3R,4R)-1-((S)-3-cyclohexyl-3-hydroxy-propyl)-3,4-dimethyl-piperidin-4-yl]-phenyl ester 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 lithium hydroxide 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  SAR and biological evaluation of novel trans-3,4-dimethyl-4-arylpiperidine derivatives as opioid antagonists

  摘要：

  The phenolic hydroxy group of opiate-derived ligands is of known importance for biological activity. We have developed a SAR study around LY255582 by comparing the effect of the hydroxy group in the 2- and 4-position of the phenyl ring. Also, we have proved that the 3-position of the phenyl ring is optimal for opioid activity. Furthermore, we have successfully replaced the hydroxy group in LY255582 by carbamate and carboxamide groups. The new analogs have high affinity for the opioid receptors comparable to the corresponding phenol. Carboxamide analog 12 has an improved metabolism profile and proved to be efficacious in in vivo studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.123
• 作为产物：
  描述：

  N-苯基双(三氟甲烷磺酰)亚胺 、 (+)-1-(3(S)-3-hydroxy-3-cyclohexylpropyl)-3(R),4(R)-dimethyl-4-(3-hydroxyphenyl)piperidine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到Trifluoro-methanesulfonic acid 3-[(3R,4R)-1-((S)-3-cyclohexyl-3-hydroxy-propyl)-3,4-dimethyl-piperidin-4-yl]-phenyl ester
  参考文献：
  名称：

  SAR and biological evaluation of novel trans-3,4-dimethyl-4-arylpiperidine derivatives as opioid antagonists

  摘要：

  The phenolic hydroxy group of opiate-derived ligands is of known importance for biological activity. We have developed a SAR study around LY255582 by comparing the effect of the hydroxy group in the 2- and 4-position of the phenyl ring. Also, we have proved that the 3-position of the phenyl ring is optimal for opioid activity. Furthermore, we have successfully replaced the hydroxy group in LY255582 by carbamate and carboxamide groups. The new analogs have high affinity for the opioid receptors comparable to the corresponding phenol. Carboxamide analog 12 has an improved metabolism profile and proved to be efficacious in in vivo studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.123