(-)-(4S)-4-amino-4-(4-methoxyphenyl)-5,5,5-trifluoropentan-2-one | 1030852-40-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (-)-(4S)-4-amino-4-(4-methoxyphenyl)-5,5,5-trifluoropentan-2-one
• 英文别名: (4S)-4-amino-5,5,5-trifluoro-4-(4-methoxyphenyl)pentan-2-one
• CAS: 1030852-40-4
• 化学式: C₁₂H₁₄F₃NO₂
• mdl: MFCD11099955
• 分子量: 261.244
• InChiKey: XUVFNTSJXAVQHH-NSHDSACASA-N

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：

  (-)-(4S)-4-amino-4-(4-methoxyphenyl)-5,5,5-trifluoropentan-2-one 、 三氟乙酰乙酸乙酯 以 甲苯 为溶剂， 以73%的产率得到(S)-(+)-6-(4-methoxyphenyl)-4-methyl-3-trifluoroacetyl-6-trifluoromethyl-5,6-dihydropyridin-2(1H)-one
  参考文献：
  名称：

  Synthesis of (S)-(+)-6-aryl-3-acetyl-6-trifluoromethyl-5,6-dihydropyridin-2(1H)-ones

  摘要：

  (S)-(+)-4-Amino-4-aryl-5,5,5-trifluoropentan-2-ones reacted with ethyl acetoacetate and ethyl trifluoroacetoacetate to give (S)-(+)-6-aryl-3-acetyl(or trifluoroacetyl)-6-trifluoromethyl-5,6-dihydropyridin-2(1H)-ones.

  DOI：

  10.1134/s1070428010070183
• 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

• Optically active 4-amino-4-aryl-5,5,5-trifluoropentan-2-ones: Versatile reagents for synthesis of chiral 4-trifluoromethyl-3,4-dihydroazin-2-ones
  作者：Volodymyr A. Sukach、Nataliya M. Golovach、Nina V. Melnichenko、Ivan F. Tsymbal、Mykhaylo V. Vovk

  DOI：10.1016/j.jfluchem.2008.09.003

  日期：2008.12

  (thio)ureas and isocyanates derived from enantiomerically enriched 4-amino-4-aryl-5,5,5-trifluoropentan-2-ones affords a novel synthetic access to chiral 4-trifluoromethyl-substituted 3,4-dihydropyrimidin-2(1H)-(thi)ones and 3,4-dihydro-1,3-oxazin-2-ones, respectively.

  衍生自对映异构体富集的4-氨基-4-芳基-5,5,5-三氟戊烷-2-酮的二取代（硫代）脲和异氰酸酯的环缩合提供了手性4-三氟甲基取代的3,4-二氢嘧啶的新颖合成途径-2（1 H）-（thi）ones和3,4-dihydro-1,3-oxazin-2-ones。
• Reaction of (S)-(+)-4-amino-4-aryl-5,5,5-trifluoropentan-2-ones with α-chlorobenzyl isocyanates. Synthesis of (S)-(+)-4-aryl-6-(2-arylethenyl)-4-trifluoromethyl-3,4-dihydro-pyrimidin-2(1H)-ones
  作者：N. M. Golovach、V. A. Sukach、M. V. Vovk

  DOI：10.1134/s1070428010100222

  日期：2010.10

  (S)-(+)-4-Amino-4-aryl-5,5,5-trifluoropentan-2-ones reacted with 6h-chlorobenzyl isocyanates with formation of (S)-(+)-4-aryl-6-(2-arylethenyl)-4-trifluoromethyl-3,4-dihydropyrimidin-2(1H)-ones.
• Synthesis of chiral 3-aryl-1-methyl-3-trifluoromethyl-3H-pyrrolizines
  作者：N. M. Golovach、V. A. Sukach、M. V. Vovk

  DOI：10.1134/s1070428009060281

  日期：2009.6
• 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 (S)-(+)-6-aryl-3-acetyl-6-trifluoromethyl-5,6-dihydropyridin-2(1H)-ones
  作者：N. M. Golovach、V. A. Sukach、M. V. Vovk

  DOI：10.1134/s1070428010070183

  日期：2010.7

  (S)-(+)-4-Amino-4-aryl-5,5,5-trifluoropentan-2-ones reacted with ethyl acetoacetate and ethyl trifluoroacetoacetate to give (S)-(+)-6-aryl-3-acetyl(or trifluoroacetyl)-6-trifluoromethyl-5,6-dihydropyridin-2(1H)-ones.