(R)-4-amino-5,5,5-trifluoro-4-phenylpentan-2-one | 1212218-67-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-4-amino-5,5,5-trifluoro-4-phenylpentan-2-one
• 英文别名: 4-amino-5,5,5-trifluoro-4-phenylpentan-2-one；(4R)-4-amino-5,5,5-trifluoro-4-phenylpentan-2-one
• CAS: 1212218-67-1
• 化学式: C₁₁H₁₂F₃NO
• mdl: MFCD11099957
• 分子量: 231.218
• InChiKey: DRMRVGAOPWTKPZ-SNVBAGLBSA-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：

  (R)-4-amino-5,5,5-trifluoro-4-phenylpentan-2-one 、 氯乙酰氯 以 甲苯 为溶剂， 反应 4.0h， 以96%的产率得到S-(-)-2-chloro-N-(1,1,1-trifluoro-4-oxo-2-phenylpentan-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：

  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

• 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.
• <i>N</i>-(Heteroarenesulfonyl)prolinamides-Catalyzed Aldol Reaction between Acetone and Aryl Trihalomethyl Ketones
  作者：Noriyuki Hara、Ryota Tamura、Yasuhiro Funahashi、Shuichi Nakamura

  DOI：10.1021/ol2001039

  日期：2011.4.1

  can be prepared by the catalytic enantioselective cross-aldol reaction of acetone with trihalomethyl ketones by using N-(8-quinolinesulfonyl)prolinamide as an organocatalyst. The MO calculations elucidate that the hydrogen bonding between the sulfonimide proton and the 8-quinolyl nitrogen atom plays an important role in exerting the enantioselectivity of the reaction.

  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。
• 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.