2-amino-5,5,5-trifluoropentanoic acid | 2365-80-2

• 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: 2-amino-5,5,5-trifluoropentanoic acid
• 英文别名: 2-azaniumyl-5,5,5-trifluoropentanoate
• CAS: 2365-80-2
• 化学式: C₅H₈F₃NO₂
• mdl: MFCD00190648
• 分子量: 171.119
• InChiKey: KTZZIDWVKLDWBF-UHFFFAOYSA-N

物化性质

• 熔点：
  254-256 °C
• 沸点：
  206.7±40.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  2-amino-5,5,5-trifluoropentanoic acid 在 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 4.0h， 生成 (2R)-2-amino-5,5,5-trifluoropentanoic acid
  参考文献：
  名称：

  MODULATORS OF SESTRIN-GATOR2 INTERACTION AND USES THEREOF

  摘要：

  本发明提供了化合物、其组合物以及使用相同的方法。

  公开号：

  US20170114080A1
• 作为产物：
  描述：

  2-(benzylamino)-5,5,5-trifluoropentanoic acid 在 20% palladium hydroxide-activated charcoal 、 氢气 、 溶剂黄146 作用下， 反应 17.0h， 生成 2-amino-5,5,5-trifluoropentanoic acid
  参考文献：
  名称：

  [EN] MODULATORS OF SESTRIN-GATOR2 INTERACTION AND USES THEREOF
  [FR] MODULATEURS DE L'INTERACTION SESTRINE-GATOR2 ET UTILISATIONS DE CES DERNIERS

  摘要：

  本发明提供了化合物、其组合物以及使用相同的方法。

  公开号：

  WO2018200625A1

文献信息

• Fluoro- and trifluoroalkyl-containing heterocyclic sulfonamide inhibitors of beta amyloid production and derivatives thereof
  申请人：Wyeth

  公开号：US20040198778A1

  公开（公告）日：2004-10-07

  Compounds of Formula (I), 1 are provided where T is CHO, CON, or C(OH)R 1 R 2 ; R 1 and R 2 are hydrogen, optionally substituted lower alkyl, CF 3 , optionally substituted alkenyl, or optionally substituted alkynyl; R 3 is hydrogen or optionally substituted lower alkyl; R 4 is (CF 3 ) n alkyl, (CF 3 ) n (substitutedalkyl), (CF 3 ) n alkylphenyl, (CF 3 ) n alkyl(substitutedphenyl), or (F) n cycloalkyl; n=1-3; R 5 is hydrogen, halogen, CF 3 , diene fused to Y when Y═C, or substituted diene fused to Y when Y═C; W, Y and Z are C, CR 6 or N where at least one of W, Y or Z are C; R 6 is hydrogen, halogen, or optionally substituted lower alkyl; X is O, S, SO 2 , or NR 7 ; R 7 is hydrogen, optionally substituted lower alkyl, optionally substituted benzyl, or optionally substituted phenyl; and R 8 is lower alkyl, CF 3 , or optionally substituted phenyl. Methods of preparing and using these compounds for inhibiting beta amyloid production and for treatment of Alzheimer's Disease and Down's syndrome are also described.

  提供了具有式(I)的化合物，其中T为CHO、CON或C(OH)R1R2；R1和R2为氢、可选择取代的较低烷基、CF3、可选择取代的烯烃或可选择取代的炔烃；R3为氢或可选择取代的较低烷基；R4为( )n烷基、( )n(取代烷基)、( )n烷基苯基、( )n烷基(取代苯基)或(F)n环烷基；n=1-3；R5为氢、卤素、 、与Y融合的双烯烃（当Y为C时）、或与Y融合的取代双烯烃（当Y为C时）；W、Y和Z为C、CR6或N，其中至少有一个为C；R6为氢、卤素或可选择取代的较低烷基；X为O、S、SO2或NR7；R7为氢、可选择取代的较低烷基、可选择取代的苄基或可选择取代的苯基；R8为较低烷基、 或可选择取代的苯基。还描述了制备和使用这些化合物来抑制β淀粉样蛋白的产生，以及治疗阿尔茨海默病和唐氏综合征的方法。
• Fluorine containing amino acids and their derivatives. 7. Synthesis and antitumor activity of α- and γ-substituted methotrexate analogs
  作者：Tadahiko Tsushima、Kenji Kawada、Shoichi Ishihara、Naomi Uchida、Osamu Shiratori、Junko Higaki、Masaharu Hirata

  DOI：10.1016/s0040-4020(01)86044-0

  日期：1988.1

  afforded a number of fluorine containing α amino acids such as β-fluorinated-alanines, 2-amino-n,n,n-trifluoroalkanoic acids, and fluorinated glutamic acids as well as other γ-heteroatom substituted glutamic acids. Here, an efficient enzymatic optical resolution using hog kidney acylase was conducted to obtain both optical isomers of 2-amino-n,n,n-trifluoroalkanoic acids. In addition, a novel sulfoxide

  α-取代的丙二酸酯的三种类型的反应，二氟甲基化，与n，n，n-三氟烷基磺酸酯的烷基化以及与2-取代的丙烯酸酯的Michael加成反应，可方便地得到许多含氟的α氨基酸，​​例如β-氟代丙氨酸。 ，2-氨基-n，n，n-三氟链烷酸和氟化谷氨酸以及其他γ-杂原子取代的谷氨酸。在此，进行了使用猪肾酰基转移酶的有效酶促光学拆分，以获得2-氨基-n，n，n-三氟链烷酸的两种旋光异构体。另外，在α-二氟甲基-α-亚磺酰丙二酸二乙酯的碱催化反应中观察到了新的亚砜重排。最后，获得的α-和γ-取代的谷氨酸用于抗肿瘤药甲氨蝶呤的化学修饰，以显示出显着的构效关系。特别是，氟取代对观察到体内抗肿瘤活性。
• Synthesis and physical chemical properties of 2-amino-4-(trifluoromethoxy)butanoic acid – a CF₃O-containing analogue of natural lipophilic amino acids
  作者：Ivan S. Kondratov、Ivan G. Logvinenko、Nataliya A. Tolmachova、Roman N. Morev、Maria A. Kliachyna、Florian Clausen、Constantin G. Daniliuc、Günter Haufe

  DOI：10.1039/c6ob02436j

  日期：——

  2-Amino-2-(trifluoromethoxy)butanoic acid (O-trifluoromethyl homoserine) was synthesized as a racemate and in both enantiomeric forms. The measured pKa and log D values establish the compound as a promising analogue of natural aliphatic amino acids.

  合成了外消旋体和两种对映体形式的2-氨基-2-（三氟甲氧基）丁酸（O-三氟甲基高丝氨酸）。测得的p K a和log  D值确定该化合物为天然脂族氨基酸的有前途的类似物。
• The Synthesis of Tenuazonic and Congeneric Tetramic Acids
  作者：Stanton A. Harris、Linda V. Fisher、Karl Folkers

  DOI：10.1021/jm00328a014

  日期：1965.7
• Inhibition of the mammalian .beta.-lactamase renal dipeptidase (dehydropeptidase-I) by Z-2-(acylamino)-3-substituted-propenoic acids
  作者：Donald W. Graham、Wallace T. Ashton、Louis Barash、Jeannette E. Brown、Ronald D. Brown、Laura F. Canning、Anna Chen、James P. Springer、Edward F. Rogers

  DOI：10.1021/jm00389a018

  日期：1987.6

  The title enzyme deactivates the potent carbapenem antibiotic imipenem in the kidney, producing low antibiotic levels in the urinary tract. A series of (Z)-2-(acylamino)-3-substituted-propenoic acids (3) are specific, competitive inhibitors of the enzyme capable of increasing the urinary concentration of imipenem in vivo. Many of the compounds were prepared in one step from an alpha-keto acid and a primary amide. The optimum R2 groups are 2,2-dimethyl, -dichloro, and -dibromocyclopropyl. With R2 = 2,2-dimethylcyclopropyl (DMCP), a wide variety of R3 groups including alkyl, oxa- and thiaalkyl, and alkyl groups containing acidic, basic, and neutral substituents give effective inhibitors with Ki values of 0.02-1 microM and a range of pharmacokinetic properties. By resolution of enantiomers and X-ray crystallography, the enzyme-inhibitory activity of the DMCP group was found to reside with the 1S isomer. The cysteinyl compound 176 (cilastatin, MK-0791) has the desired pharmacological properties and has been chosen for combination with imipenem.