(S)-(-)-2-trifluoroacetylamino-7-methoxy-1,2,3,4-tetrahydronaphthalene | 137589-11-8

• 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-7-methoxy-1,2,3,4-tetrahydronaphthalene
• 英文别名: 2,2,2-trifluoro-N-[(2S)-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl]acetamide
• CAS: 137589-11-8
• 化学式: C₁₃H₁₄F₃NO₂
• 分子量: 273.255
• InChiKey: JPOASSFANLERCW-JTQLQIEISA-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-7-methoxy-1,2,3,4-tetrahydronaphthalene 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以50%的产率得到(S)-7-甲氧基-2-氨基四氢化萘盐酸盐
  参考文献：
  名称：

  Synthesis and β-adrenergic activity of atypical β-adrenergic phenylethanolaminotetralin stereoisomers

  摘要：

  A series of substituted phenylethanolaminotetralins were synthesized as pure stereoisomers and their ability to stimulate atypical beta-adrenoceptors selectively was evaluated. The compounds in vitro relative potencies were assessed using the atypical beta response of inhibition of rat proximal colon motility and the typical beta 1 (increase in guinea-pig right atrial frequency) and beta 2 (guinea-pig tracheal relaxation and rat uterus motility inhibition) responses. Compound 42 (SR 58611A) was found to be the most potent and selective.

  DOI：

  10.1016/0223-5234(94)90095-7
• 作为产物：
  描述：

  (S)-(-)-1-oxo-2-trifluoroacetylamino-7-methoxy-1,2,3,4-tetrahydronaphthalene 在 palladium on activated charcoal 硫酸 、 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以59%的产率得到(S)-(-)-2-trifluoroacetylamino-7-methoxy-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Synthesis and β-adrenergic activity of atypical β-adrenergic phenylethanolaminotetralin stereoisomers

  摘要：

  A series of substituted phenylethanolaminotetralins were synthesized as pure stereoisomers and their ability to stimulate atypical beta-adrenoceptors selectively was evaluated. The compounds in vitro relative potencies were assessed using the atypical beta response of inhibition of rat proximal colon motility and the typical beta 1 (increase in guinea-pig right atrial frequency) and beta 2 (guinea-pig tracheal relaxation and rat uterus motility inhibition) responses. Compound 42 (SR 58611A) was found to be the most potent and selective.

  DOI：

  10.1016/0223-5234(94)90095-7

文献信息

• Asymmetric catalytic aziridination of dihydronaphthalenes for the preparation of substituted 2-aminotetralins
  作者：Jon Erik Aaseng、Silje Melnes、Gard Reian、Odd R. Gautun

  DOI：10.1016/j.tet.2010.11.010

  日期：2010.12

  An enantioselective synthesis of substituted 2-aminotetralins from dihydronaphthalenes in four steps is described. The key step is the Jacobsen's (diimine)copper-catalyzed asymmetric aziridination of dihydronaphthalenes to the respective aziridines in 33-82% yields and 60-87% enantiomeric excess. The enantioselectivity and the yield were dependent on the properties of the nitrene precursor. pTs=NIPh appeared in general to give better results than pNsN=IPh. Aziridines were ring-opened in the benzylic position by catalytic hydrogenolysis in quantitative yields, and deprotected in two steps to the respective 2-aminotetralins in 66-85% yields. The synthesis of (S)-2-aminotetralin (>98% ee) and (S)-2-amino-7-methoxytetralin (56% ee) were accomplished in 30 and 52% overall yields, respectively. (C) 2010 Elsevier Ltd. All rights reserved.
• 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.
• Synthesis and β-adrenergic activity of atypical β-adrenergic phenylethanolaminotetralin stereoisomers
  作者：R Cecchi、T Croci、R Boigegrain、S Boveri、M Baroni、G Boccardi、JP Guimbard、U Guzzi

  DOI：10.1016/0223-5234(94)90095-7

  日期：1994.1

  A series of substituted phenylethanolaminotetralins were synthesized as pure stereoisomers and their ability to stimulate atypical beta-adrenoceptors selectively was evaluated. The compounds in vitro relative potencies were assessed using the atypical beta response of inhibition of rat proximal colon motility and the typical beta 1 (increase in guinea-pig right atrial frequency) and beta 2 (guinea-pig tracheal relaxation and rat uterus motility inhibition) responses. Compound 42 (SR 58611A) was found to be the most potent and selective.