(-)-(4S)-4-amino-4-phenyl-5,5,5-trifluoropentan-2-one | 1030852-36-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (-)-(4S)-4-amino-4-phenyl-5,5,5-trifluoropentan-2-one
• 英文别名: (S)-(+)-4-amino-4-phenyl-5,5,5-trifluoro-2-pentanone；(S)-4-amino-5,5,5-trifluoro-4-phenylpentan-2-one；4-amino-5,5,5-trifluoro-4-phenylpentan-2-one；(4S)-4-amino-5,5,5-trifluoro-4-phenylpentan-2-one
• CAS: 1030852-36-8
• 化学式: C₁₁H₁₂F₃NO
• mdl: MFCD11099952
• 分子量: 231.218
• InChiKey: DRMRVGAOPWTKPZ-JTQLQIEISA-N

物化性质

• 沸点：
  292.0±40.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-(4S)-4-amino-4-phenyl-5,5,5-trifluoropentan-2-one 、 2-(三氟甲基)苯基异硫代氰酸酯 以 乙腈 为溶剂， 反应 10.0h， 以65%的产率得到(S)-(-)-6-methyl-4-trifluoromethyl-1-[2-(trifluoromethyl)phenyl]-4-phenyl-3,4-dihydropyrimidine-2(1H)-thione
  参考文献：
  名称：

  Synthesis of (S)-(-)-1,4-diaryl-6-methyl-4-trifluoromethyl-3,4-dihydropyrimidine-2(1H)-thiones

  摘要：

  (S)-(+)-4-Amino-4-aryl-5,5,5-trifluoropentan-2-one reacted with aryl isothiocyanates containing electron-withdrawing substituents to give (S)-(-)-1,4-diaryl-6-methyl-4-trifluoromethyl-3,4-dihydropyrimidine-2(1H)-thiones.

  DOI：

  10.1134/s1070428012030165
• 作为产物：
  描述：

  1-phenyl-2,2,2-trifluoroethylideneimine 、 丙酮 在 N-(8-quinolinesulfonyl)prolinamide*TFA 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (-)-(4S)-4-amino-4-phenyl-5,5,5-trifluoropentan-2-one 、 (R)-4-amino-5,5,5-trifluoro-4-phenylpentan-2-one
  参考文献：
  名称：

  N-（杂芳烃磺酰基）脯氨酰胺-丙酮与芳基三卤代甲基酮之间的羟醛催化反应

  摘要：

  可以通过使用N-（8-喹啉磺酰基）脯氨酰胺作为有机催化剂，通过丙酮与三卤代甲基酮的催化对映选择性交联醇醛缩合反应来制备具有季手性碳中心的对映体富集的三卤代甲基取代的醇。MO计算表明，磺酰亚胺质子和8-喹啉基氮原子之间的氢键在施加反应的对映选择性方面起重要作用。

  DOI：

  10.1021/ol2001039

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。
• Asymmetric organocatalytic mannich reaction of 1-aryl-2,2,2-trifluoroethylidenecarbamic acid derivatives with acetone
  作者：N. M. Golovach、V. N. Tkachuk、V. A. Sukach、M. V. Vovk

  DOI：10.1134/s1070428012090060

  日期：2012.9

  Mannich reactions of ethyl 1-aryl-2,2,2-trifluoroethylidenecarbamates and ureas with acetone in the presence of L-proline gave 1-aryl-3-oxo-1-(trifluoromethyl)butylcarbamates and ureas with an enantiomeric excess of 24-54%.
• 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.
• 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 (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.