(+/-)-trans-N-[2-(7-methoxy-3-phenyl-1,2,3,4-tetrahydro-naphthalen-1-yl)ethyl]cyclobutyl carboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+/-)-trans-N-[2-(7-methoxy-3-phenyl-1,2,3,4-tetrahydro-naphthalen-1-yl)ethyl]cyclobutyl carboxamide
• 英文别名: N-[2-[(1S,3R)-7-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl]ethyl]cyclobutanecarboxamide
• 化学式: C₂₄H₂₉NO₂
• 分子量: 363.5
• InChiKey: CHNMYFQAXCNAFN-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(7-methoxy-3-phenyl-1,2,3,4-tetrahydro-naphthalen-1-yl)ethylamine hydrochloride 、 环丁基甲酰氯 在 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以33%的产率得到(+/-)-cis-N-[2-(7-methoxy-3-phenyl-1,2,3,4-tetrahydro-naphthalen-1-yl)ethyl]cyclobutyl carboxamide
  参考文献：
  名称：

  Design and synthesis of 3-phenyl tetrahydronaphthalenic derivatives as new selective MT2 melatoninergic ligands

  摘要：

  Tetrahydronaphthalenic analogues of melatonin have been synthesized and evaluated as melatonin receptor ligands. Introduction of a phenyl substituent in the 3-position of the tetraline ring allows to obtain MT2 selective ligands. Activity and MT2 selectivity can be modulated with suitable modifications of the N-acyl substituent. The (+)-(RR)-cis enantiomer of the N-[2-(7-methoxy-3-phenyl-1,2,3,4-tetrahydro-naphthalen-1-yl)ethyl]cyclobutyl carboxamide (14) is one of the most MT2 selective ligands described until now and behaves as an antagonist. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00473-x

文献信息

• Design and synthesis of 3-phenyl tetrahydronaphthalenic derivatives as new selective MT2 melatoninergic ligands
  作者：Saı̈d Yous、Sophie Durieux-Poissonnier、Emmanuelle Lipka-Belloli、Halim Guelzim、Christophe Bochu、Valérie Audinot、Jean A Boutin、Philippe Delagrange、Caroline Bennejean、Pierre Renard、Daniel Lesieur

  DOI：10.1016/s0968-0896(02)00473-x

  日期：2003.3

  Tetrahydronaphthalenic analogues of melatonin have been synthesized and evaluated as melatonin receptor ligands. Introduction of a phenyl substituent in the 3-position of the tetraline ring allows to obtain MT2 selective ligands. Activity and MT2 selectivity can be modulated with suitable modifications of the N-acyl substituent. The (+)-(RR)-cis enantiomer of the N-[2-(7-methoxy-3-phenyl-1,2,3,4-tetrahydro-naphthalen-1-yl)ethyl]cyclobutyl carboxamide (14) is one of the most MT2 selective ligands described until now and behaves as an antagonist. (C) 2002 Elsevier Science Ltd. All rights reserved.