(2S)-3,3,3-trifluoro-2-methylpropanoic acid | 160290-20-0

• 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: (2S)-3,3,3-trifluoro-2-methylpropanoic acid
• 英文别名: (S)-α-trifluoromethylpropanoic acid；(S)-3,3,3-trifluoro-2-methylpropanoic acid
• CAS: 160290-20-0
• 化学式: C₄H₅F₃O₂
• 分子量: 142.078
• InChiKey: DQOGDQIDOONUSK-REOHCLBHSA-N

物化性质

• 沸点：
  139.5±35.0 °C(Predicted)
• 密度：
  1.340±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (2S)-3,3,3-trifluoro-2-methylpropanoic acid 以 乙醚 为溶剂， 生成 (S)-3,3,3-Trifluoro-2-methyl-propionic acid methyl ester
  参考文献：
  名称：

  Preparation of Optically Active 2-(Trifluoromethyl)alkan-1-ols by Catalytic Asymmetric Hydrogenation.

  摘要：

  在Ru-2, 2'-双(二苯基膦)-1, 1'-联萘（Ru-BINAP）和Rh-BINAP的催化下，对（E）-2-（三氟甲基）-2-烯-1-醇进行了加氢反应，获得了良好的对映体过量（ee为71-83%）。在Ru-BINAP的催化下，2-（三氟甲基）丙烯酸被转化为相应的饱和酸，其酯化和还原反应产生了光学活性2-（三氟甲基）-1-丙醇，ee为80%。

  DOI：

  10.1248/cpb.44.477
• 作为产物：
  描述：

  (2S,3S)-1,3-dihydroxybutan-2-aminium (S)-3,3,3-trifluoro-2-methylpropanoate 在 盐酸 作用下， 以 水 为溶剂， 以100%的产率得到(2S)-3,3,3-trifluoro-2-methylpropanoic acid
  参考文献：
  名称：

  Synthesis of ( R )- and ( S )-α-trifluoromethyl propanoic acids via asymmetric hydrogenation followed by salt resolution

  摘要：

  A highly enantioselective synthesis of (R)- and (S)-alpha-trifluoromethyl (CF3) propanoic acids has been achieved via asymmetric hydrogenation of 2-trifluoromethylacrylic acid using RuBINAP-Cl-2 catalyst followed by salt resolution with threoninol. Both enantiomers can be obtained as threoninol salts in good yield and with high enantiomeric excess. Amide coupling conditions that minimize racemization of the chiral acid have also been developed. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.07.004

文献信息

• PYRIDINYL PYRAZOLES AS MODULATORS OF RORyT
  申请人：Janssen Pharmaceutica NV

  公开号：US20190382350A1

  公开（公告）日：2019-12-19

  The present invention comprises compounds of Formula I. wherein: R 1 , R 3 , R 4 , R 5 , R 6 , and Q are defined in the specification. The invention also comprises a method of treating or ameliorating a ROR-γ-t mediated syndrome, disorder or disease, including wherein the syndrome, disorder or disease is selected from the group consisting of rheumatoid arthritis, psoriatic arthritis, and psoriasis. The invention also comprises a method of modulating RORγt activity in a mammal by administration of a therapeutically effective amount of at least one compound of Formula I.

  本发明涵盖了Formula I的化合物。 其中： R1、R3、R4、R5、R6和Q在规范中有定义。 该发明还涵盖了一种治疗或改善ROR-γ-t介导的综合症、疾病或疾病的方法，包括综合症、疾病或疾病选自类风湿性关节炎、银屑病性关节炎和牛皮癣的群组。该发明还涵盖了通过给哺乳动物施用至少一种Formula I化合物的治疗有效量来调节RORγt活性的方法。
• PHENYL SUBSTITUTED PYRAZOLES AS MODULATORS OF RORgT
  申请人：Janssen Pharmaceutica NV

  公开号：US20190382349A1

  公开（公告）日：2019-12-19

  The present invention comprises compounds of Formula I. wherein: R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and Q are defined in the specification. The invention also comprises a method of treating or ameliorating a ROR-γ-t mediated syndrome, disorder or disease, including wherein the syndrome, disorder or disease is selected from the group consisting of rheumatoid arthritis, psoriatic arthritis, and psoriasis. The invention also comprises a method of modulating RORγt activity in a mammal by administration of a therapeutically effective amount of at least one compound of Formula I.

  本发明涵盖了Formula I的化合物。 其中： R1、R3、R4、R5、R6、R7、R8和Q在规范中有定义。 该发明还涵盖了一种治疗或改善ROR-γ-t介导的综合征、疾病或疾病的方法，包括综合征、疾病或疾病选自类风湿性关节炎、银屑病性关节炎和牛皮癣的群组。该发明还涵盖了通过给哺乳动物施用至少一种Formula I化合物的治疗有效量来调节RORγt活性的方法。
• Lipase mediated preparation of the enantiomers of 3,3,3-trifluoro-2-methylpropanoic acid
  作者：Petr Beier、Alexandra M. Z. Slawin、David O’Hagan

  DOI：10.1016/j.tetasy.2004.07.014

  日期：2004.8

  The preparation of both enantiomers of 3,3,3-trifluoro-2-methylpropanoic acid by a lipase mediated kinetic resolution of the racemate is described.

  描述了通过脂肪酶介导的外消旋体的动力学拆分制备3,3,3-三氟-2-甲基丙酸的两种对映体。
• Synthesis of ( R )- and ( S )-α-trifluoromethyl propanoic acids via asymmetric hydrogenation followed by salt resolution
  作者：Ming Z. Chen、Neal W. Sach、Philippe Nuhant、Olugbeminiyi O. Fadeyi、John Trujillo、Vincent Lombardo、Louise Bernier、Ray Unwalla、Andrew C. Flick

  DOI：10.1016/j.tetasy.2016.07.004

  日期：2016.10

  A highly enantioselective synthesis of (R)- and (S)-alpha-trifluoromethyl (CF3) propanoic acids has been achieved via asymmetric hydrogenation of 2-trifluoromethylacrylic acid using RuBINAP-Cl-2 catalyst followed by salt resolution with threoninol. Both enantiomers can be obtained as threoninol salts in good yield and with high enantiomeric excess. Amide coupling conditions that minimize racemization of the chiral acid have also been developed. (C) 2016 Elsevier Ltd. All rights reserved.
• Preparation of Optically Active 2-(Trifluoromethyl)alkan-1-ols by Catalytic Asymmetric Hydrogenation.
  作者：Katsuhiko ISEKI、Yoshichika KUROKI、Takabumi NAGAI、Yoshiro KOBAYASHI

  DOI：10.1248/cpb.44.477

  日期：——

  The hydrogenation of (E)-2-(trifluoromethyl)alk-2-en-1-ols catalyzed by Ru-2, 2'-bis(diphynylphosphino)-1, 1'-binaphthyl (Ru-BINAP) and Rh-BINAP was carried out with good enantiomeric excess (71-83% ee). Ru-BINAP-catalyzed hydrogenation converted 2-(trifluoromethyl)acrylic acid to the corresponding saturated acid whose esterification and reduction provided optically active 2-(trifluoromethyl)propan-1-ol in 80% ee.

  在Ru-2, 2'-双(二苯基膦)-1, 1'-联萘（Ru-BINAP）和Rh-BINAP的催化下，对（E）-2-（三氟甲基）-2-烯-1-醇进行了加氢反应，获得了良好的对映体过量（ee为71-83%）。在Ru-BINAP的催化下，2-（三氟甲基）丙烯酸被转化为相应的饱和酸，其酯化和还原反应产生了光学活性2-（三氟甲基）-1-丙醇，ee为80%。