(4R)-4-amino-5,5,5-trifluoro-4-(4-methoxyphenyl)pentan-2-one | 1212262-35-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4R)-4-amino-5,5,5-trifluoro-4-(4-methoxyphenyl)pentan-2-one
• CAS: 1212262-35-5
• 化学式: C₁₂H₁₄F₃NO₂
• mdl: MFCD11099960
• 分子量: 261.244
• InChiKey: XUVFNTSJXAVQHH-LLVKDONJSA-N

物化性质

• 沸点：
  337.3±42.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R)-4-amino-5,5,5-trifluoro-4-(4-methoxyphenyl)pentan-2-one 、 氯乙酰氯 以 甲苯 为溶剂， 反应 4.0h， 以79%的产率得到S-(+)-2-chloro-N-(1,1,1-trifluoro-2-(4-methoxyphenyl)-4-oxopentan-2-yl)acetamide
  参考文献：
  名称：

  Synthesis of (7S)-(−)-7-aryl-5-methyl-7-trifluoromethyl-1,3,6,7-tetrahydro-2H-1,4-diazepin-2-ones

  摘要：

  Acylation of (S)-(-)-4-amino-4-aryl-5,5,5-trifluoropentan-2-ones with chloroacetyl chloride gave the corresponding chloroacetamides which were treated with sodium azide and then with triphenylphosphine to obtain triphenyl-lambda(5)-phosphanylideneaminoacetic acid amides. The latter underwent thermal (boiling toluene) or base-catalyzed (NaOH/MeOH) intramolecular cyclization with elimination of triphenylphosphine oxide and formation of (7S)-(-)-7-aryl-5-methyl-7-trifluoromethyl-1,3,6,7-tetrahydro-2H-1,4-diazepin-2-ones.

  DOI：

  10.1134/s1070428010040044
• 作为产物：
  描述：

  2,2,2-trifluoro-1-(4-methoxyphenyl)ethan-1-imine 、 丙酮 在 L-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 反应 72.0h， 生成 (-)-(4S)-4-amino-4-(4-methoxyphenyl)-5,5,5-trifluoropentan-2-one 、 (4R)-4-amino-5,5,5-trifluoro-4-(4-methoxyphenyl)pentan-2-one
  参考文献：
  名称：

  Convenient enantioselective synthesis of β-trifluoromethyl-β-aminoketones by organocatalytic asymmetric Mannich reaction of aryl trifluoromethyl ketimines with acetone

  摘要：

  The L-proline-catalyzed asymmetric Mannich reaction has been performed between aryl trifluoromethyl ketimines and acetone to provide, for the first time, chiral beta-aryl-beta-trifluoromethyl-beta-aminoketones in high yields and with 74-92% enantiomeric excesses. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.02.023

文献信息

• Convenient enantioselective synthesis of β-trifluoromethyl-β-aminoketones by organocatalytic asymmetric Mannich reaction of aryl trifluoromethyl ketimines with acetone
  作者：Volodymyr A. Sukach、Nataliya M. Golovach、Volodymyr V. Pirozhenko、Eduard B. Rusanov、Mykhaylo V. Vovk

  DOI：10.1016/j.tetasy.2008.02.023

  日期：2008.4

  The L-proline-catalyzed asymmetric Mannich reaction has been performed between aryl trifluoromethyl ketimines and acetone to provide, for the first time, chiral beta-aryl-beta-trifluoromethyl-beta-aminoketones in high yields and with 74-92% enantiomeric excesses. (c) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of (7S)-(−)-7-aryl-5-methyl-7-trifluoromethyl-1,3,6,7-tetrahydro-2H-1,4-diazepin-2-ones
  作者：M. V. Vovk、N. M. Golovach、V. A. Sukach、O. N. Chernyuk、O. V. Manoilenko

  DOI：10.1134/s1070428010040044

  日期：2010.4

  Acylation of (S)-(-)-4-amino-4-aryl-5,5,5-trifluoropentan-2-ones with chloroacetyl chloride gave the corresponding chloroacetamides which were treated with sodium azide and then with triphenylphosphine to obtain triphenyl-lambda(5)-phosphanylideneaminoacetic acid amides. The latter underwent thermal (boiling toluene) or base-catalyzed (NaOH/MeOH) intramolecular cyclization with elimination of triphenylphosphine oxide and formation of (7S)-(-)-7-aryl-5-methyl-7-trifluoromethyl-1,3,6,7-tetrahydro-2H-1,4-diazepin-2-ones.