(-)-(R)-α-phenyl-α-trifluoromethylglycine | 1281952-37-1

• 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: (-)-(R)-α-phenyl-α-trifluoromethylglycine
• 英文别名: 3,3,3-Trifluoro-2-phenylalanine；(2R)-2-amino-3,3,3-trifluoro-2-phenylpropanoic acid
• CAS: 1281952-37-1
• 化学式: C₉H₈F₃NO₂
• 分子量: 219.163
• InChiKey: FUPRWUOOEKSLDF-MRVPVSSYSA-N

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：

  (-)-(R)-α-phenyl-α-trifluoromethylglycine 、 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， 生成 (-)-(R)-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：

  5-Phenyl-5-(trifluormethyl)imidazolidin-2,4-dion 在 barium hydroxide octahydrate 作用下， 以 乙醇 、 水 为溶剂， 反应 120.0h， 生成 (-)-(R)-α-phenyl-α-trifluoromethylglycine
  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

文献信息

• 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.