α-amino-α-trifluoromethyl-phenylacetic acid | 127048-25-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: α-amino-α-trifluoromethyl-phenylacetic acid
• 英文别名: (+/-)-α-phenyl-α-trifluoromethylglycine；2-(trifluoromethyl)phenylglycine；α-CF3-PhGly；2-Amino-3,3,3-trifluoro-2-phenylpropanoic acid
• CAS: 127048-25-3
• 化学式: C₉H₈F₃NO₂
• 分子量: 219.163
• InChiKey: FUPRWUOOEKSLDF-UHFFFAOYSA-N

物化性质

• 熔点：
  245 °C (sublm)
• 沸点：
  309.5±42.0 °C(Predicted)
• 密度：
  1.420±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  α-amino-α-trifluoromethyl-phenylacetic acid 、 三甲基硅烷化重氮甲烷 在 甲醇 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 0.5h， 以70%的产率得到α-phenyl-α-trifluoromethylglycine methyl ester
  参考文献：
  名称：

  Efficient preparation of enantiomerically pure α-aryl-α-trifluoromethylglycines via Auto Seeded Programmed Polythermic Preferential Crystallization of 5-aryl-5-trifluoromethylhydantoins

  摘要：

  Both pure enantiomers of alpha-phenyl- (or alpha-(p-methoxyphenyl))-alpha-trifluoromethyl-glycine and their corresponding methyl esters were obtained on a preparative scale using the following four-step sequence: the preparation of 5-aryl-5-trifluoromethylhydantoins by a Bucherer-Bergs reaction starting from trifluoromethyl aryl ketones, optical resolution by Auto Seeded Programmed Polythermic Preferential Crystallization (AS3PC), basic hydrolysis of the enantiopure hydantoins by means of aqueous barium hydroxide, and esterification of the amino acids with trimethylsilyldiazomethane. Hydantoins 5 and 6 were proven to crystallize as conglomerates using first second harmonic generation and then X-ray powder diffraction. The absolute stereochemistry of (+)-5-phenyl-5-trifluoromethylhydantoin 5b was established to be (S) by X-ray diffraction analysis on a single-crystal. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.029
• 作为产物：
  描述：

  1-phenyl-2,2,2-trifluoroethylideneimine 在 盐酸 、 三乙胺 作用下， 反应 22.0h， 生成 α-amino-α-trifluoromethyl-phenylacetic acid
  参考文献：
  名称：

  α-氨基-α-三氟甲基-苯基乙腈：用于19 F NMR测定酸的对映体纯度的潜在试剂

  摘要：

  α氨基α三氟甲基-苯基乙腈，光子晶体（CF 3）（CN）NH 2，2，其中，所述氨基位于一个拥挤的，手性，季碳中心，已经研究了作为潜在的试剂19 F NMR通过转化为相应的非对映异构酰胺确定手性酸的对映体纯度。由胺2制备的R，R / S，S与R，S / S，R非对映异构酰胺（8a–j）的19 F NMR化学位移（Δδ）的差异十种手性酸的含量最高为0.266 ppm。十个示例中的八个具有的Δδ超过了0.02 ppm的有用最小值。这些值明显优于其他已知试剂的值。

  DOI：

  10.1016/s0040-4020(01)80341-0

文献信息

• α-Amino-α-trifluoromethyl-phenylacetonitrile: A potential reagent for 19F NMR determination of enantiomeric purity of acids
  作者：Miroslav Koos、Harry S. Mosher

  DOI：10.1016/s0040-4020(01)80341-0

  日期：——

  the amino group is located on a crowded, chiral, quaternary carbon center, has been studied as a potential reagent for the 19F NMR determination of enantiomeric purity of chiral acids by conversion to their corresponding diastereomeric amides. The differences in the 19F NMR chemical shifts (Δδ) of the R,R/S,S versus R,S/S,R diastereomeric amides (8a–j) prepared from amine 2 and ten chiral acids range

  α氨基α三氟甲基-苯基乙腈，光子晶体（CF 3）（CN）NH 2，2，其中，所述氨基位于一个拥挤的，手性，季碳中心，已经研究了作为潜在的试剂19 F NMR通过转化为相应的非对映异构酰胺确定手性酸的对映体纯度。由胺2制备的R，R / S，S与R，S / S，R非对映异构酰胺（8a–j）的19 F NMR化学位移（Δδ）的差异十种手性酸的含量最高为0.266 ppm。十个示例中的八个具有的Δδ超过了0.02 ppm的有用最小值。这些值明显优于其他已知试剂的值。
• Efficient preparation of enantiomerically pure α-aryl-α-trifluoromethylglycines via Auto Seeded Programmed Polythermic Preferential Crystallization of 5-aryl-5-trifluoromethylhydantoins
  作者：Thibaut Martin、Cédrik Massif、Nicolas Wermester、Julie Linol、Séverine Tisse、Pascal Cardinael、Gérard Coquerel、Jean-Philippe Bouillon

  DOI：10.1016/j.tetasy.2010.11.029

  日期：2011.1

  Both pure enantiomers of alpha-phenyl- (or alpha-(p-methoxyphenyl))-alpha-trifluoromethyl-glycine and their corresponding methyl esters were obtained on a preparative scale using the following four-step sequence: the preparation of 5-aryl-5-trifluoromethylhydantoins by a Bucherer-Bergs reaction starting from trifluoromethyl aryl ketones, optical resolution by Auto Seeded Programmed Polythermic Preferential Crystallization (AS3PC), basic hydrolysis of the enantiopure hydantoins by means of aqueous barium hydroxide, and esterification of the amino acids with trimethylsilyldiazomethane. Hydantoins 5 and 6 were proven to crystallize as conglomerates using first second harmonic generation and then X-ray powder diffraction. The absolute stereochemistry of (+)-5-phenyl-5-trifluoromethylhydantoin 5b was established to be (S) by X-ray diffraction analysis on a single-crystal. (C) 2010 Elsevier Ltd. All rights reserved.