(S)-2-trifluoroacetylamino-5-methoxy-1,2,3,4-terahydronaphthalene | 735279-24-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (S)-2-trifluoroacetylamino-5-methoxy-1,2,3,4-terahydronaphthalene
• 英文别名: (S)-2-trifluoroacetylamino-5-methoxy-1,2,3,4-tetrahydronaphthalene；2,2,2-trifluoro-N-[(2S)-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl]acetamide
• CAS: 735279-24-0
• 化学式: C₁₃H₁₄F₃NO₂
• 分子量: 273.255
• InChiKey: QTVYIWGAEBMAEV-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• 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：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-trifluoroacetylamino-5-methoxy-1,2,3,4-terahydronaphthalene 在 盐酸 、 四(三苯基膦)钯 、 三溴化硼 、 sodium carbonate 、 溶剂黄146 、 三乙胺 、 lithium chloride 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 8.0h， 生成 (S)-5-(2,6-Dimethoxy-phenyl)-1,2,3,4-tetrahydro-naphthalen-2-ylamine
  参考文献：
  名称：

  Novel 2-Aminotetralin and 3-AminoChroman Derivatives as Selective Serotonin 5-HT₇ Receptor Agonists and Antagonists

  摘要：

  The understanding of the physiological role of the G-protein coupled serotonin 5-HT7 receptor is largely rudimentary. Therefore, selective and potent pharmacological tools will add to the understanding of serotonergic effects mediated through this receptor. In this report, we describe two compound classes, chromans and tetralins, encompassing compounds with nanomolar affinity for the 5-HT7 receptor and with good selectivity. Within theses classes, we have discovered both agonists and antagonists that can be used for further understanding of the pharmacology of the 5-HT7 receptor.

  DOI：

  10.1021/jm0498102
• 作为产物：
  描述：

  (R)-tert-butyl 4-iodo-1-(3-methoxyphenyl)-butan-2-yl(2,2,2-trifluoroacetyl)carbamate 在 indium(III) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以26%的产率得到(S)-(-)-2-trifluoroacetylamino-7-methoxy-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Synthesis of (S)-2-amino-7-methoxytetralin and isoindolo[1,2-a]isoquinolinone derivatives from l-aspartic acid

  摘要：

  This paper describes a new total synthesis for (S)-2-amino-7-methoxytetralin, (S)-7-MeO-AT, from L-aspartic acid in an overall yield of 10% over nine steps. The major loss was ascribed to a key intramolecular Friedel-Crafts cyclization step, which afforded up to 36% yield. Attempts to perform a Friedel-Crafts cyclization of an intermediate phthalimide protected amino alcohol 13 did not give the desired protected (S)-7-MeO-AT. On the other hand, two new isoindolo[1,2-alpha]isoquinolinone derivatives 14 and 15, were isolated in 21 and 11% yield, respectively. The yield of 15 was improved to 70%. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2014.06.008

文献信息

• Novel 2-Aminotetralin and 3-AminoChroman Derivatives as Selective Serotonin 5-HT₇ Receptor Agonists and Antagonists
  作者：Pär Holmberg、Daniel Sohn、Robert Leideborg、Patrizia Caldirola、Pavel Zlatoidsky、Sverker Hanson、Nina Mohell、Susanne Rosqvist、Gunnar Nordvall、Anette M. Johansson、Rolf Johansson

  DOI：10.1021/jm0498102

  日期：2004.7.1

  The understanding of the physiological role of the G-protein coupled serotonin 5-HT7 receptor is largely rudimentary. Therefore, selective and potent pharmacological tools will add to the understanding of serotonergic effects mediated through this receptor. In this report, we describe two compound classes, chromans and tetralins, encompassing compounds with nanomolar affinity for the 5-HT7 receptor and with good selectivity. Within theses classes, we have discovered both agonists and antagonists that can be used for further understanding of the pharmacology of the 5-HT7 receptor.
• Synthesis of (S)-2-amino-7-methoxytetralin and isoindolo[1,2-a]isoquinolinone derivatives from l-aspartic acid
  作者：Jon Erik Aaseng、Odd R. Gautun

  DOI：10.1016/j.tet.2014.06.008

  日期：2014.8

  This paper describes a new total synthesis for (S)-2-amino-7-methoxytetralin, (S)-7-MeO-AT, from L-aspartic acid in an overall yield of 10% over nine steps. The major loss was ascribed to a key intramolecular Friedel-Crafts cyclization step, which afforded up to 36% yield. Attempts to perform a Friedel-Crafts cyclization of an intermediate phthalimide protected amino alcohol 13 did not give the desired protected (S)-7-MeO-AT. On the other hand, two new isoindolo[1,2-alpha]isoquinolinone derivatives 14 and 15, were isolated in 21 and 11% yield, respectively. The yield of 15 was improved to 70%. (C) 2014 Published by Elsevier Ltd.