(S)-2-trifluoroacetylamino-1,2,3,4-tetrahydro-naphthalene | 1262722-75-7

• 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-1,2,3,4-tetrahydro-naphthalene
• 英文别名: 2,2,2-trifluoro-N-[(2S)-1,2,3,4-tetrahydronaphthalen-2-yl]acetamide
• CAS: 1262722-75-7
• 化学式: C₁₂H₁₂F₃NO
• 分子量: 243.229
• InChiKey: YYYXOONORQHFOM-JTQLQIEISA-N

物化性质

• 沸点：
  338.9±42.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-trifluoroacetylamino-1,2,3,4-tetrahydro-naphthalene 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 22.5h， 以81%的产率得到(S)-1,2,3,4-四氢-2-萘胺
  参考文献：
  名称：

  Asymmetric catalytic aziridination of dihydronaphthalenes for the preparation of substituted 2-aminotetralins

  摘要：

  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.

  DOI：

  10.1016/j.tet.2010.11.010
• 作为产物：
  描述：

  (S)-2-(p-methylbenzenesulfonyl)amino-1,2,3,4-tetrahydronaphthalene 、 三氟乙酸酐 在 三乙胺 、 samarium diiodide 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 2.5h， 以82%的产率得到(S)-2-trifluoroacetylamino-1,2,3,4-tetrahydro-naphthalene
  参考文献：
  名称：

  Asymmetric catalytic aziridination of dihydronaphthalenes for the preparation of substituted 2-aminotetralins

  摘要：

  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.

  DOI：

  10.1016/j.tet.2010.11.010

文献信息

• Chemoenzymatic Dynamic Kinetic Resolution of Primary Amines Catalyzed by CAL-B at 38–40 °C
  作者：Florent Poulhès、Nicolas Vanthuyne、Michèle P. Bertrand、Stéphane Gastaldi、Gérard Gil

  DOI：10.1021/jo201256w

  日期：2011.9.2

  The (R)-selective chemoenzymatic dynamic kinetic resolution of primary amines was performed at 38-40 degrees C in MTBE, in good to high yields and with high enantiomeric excesses. These reactions associating CAL-B to octanethiol as radical racemizing agent were carried out in the presence of methyl beta-methoxy propanoate as acyl donor, under photochemical irradiation at 350 nm in glassware.