(R)-2-amino-3,3,3-trifluoropropanoic acid

• 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)-2-amino-3,3,3-trifluoropropanoic acid
• 英文别名: (R)-(+)-3,3,3-trifluoroalanine；(R)-3,3,3-trifluoroalanine；3,3,3-trifluoroalanine；L-trifluoroalanine；3,3,3-trifluoro-D-alanine；β,β,β-trifluoroalanine；(2R)-2-azaniumyl-3,3,3-trifluoropropanoate
• 化学式: C₃H₄F₃NO₂
• 分子量: 143.065
• InChiKey: HMJQKIDUCWWIBW-PVQJCKRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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)-2-amino-3,3,3-trifluoropropanoic acid 、 sodium nitrite 、 溴化钾 在 ice-salt 、 乙醚 、 水 、 magnesium sulfate 作用下， 以 硫酸 为溶剂， 反应 1.0h， 以to yield 2-bromo-3,3,3-trifluoropropanoic acid的产率得到2-溴-3,3,3-三氟丙酸
  参考文献：
  名称：

  Halogenated substituted mercaptoacylamino acids

  摘要：

  新的卤代硫醇酰胺氨基酸，其一般式为##STR1##及其碱性盐作为降压剂是有用的。

  公开号：

  US04241076A1
• 作为产物：
  描述：

  (-)-(2R)-N-benzyloxycarbonyl-3,3,3-trifluoroalanine 在 palladium dihydroxide 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以64%的产率得到(R)-2-amino-3,3,3-trifluoropropanoic acid
  参考文献：
  名称：

  New Versatile Fluorinated Chiral Building Blocks:  Synthesis and Reactivity of Optically Pure α-(Fluoroalkyl)-β-sulfinylenamines

  摘要：

  Efficient synthesis of optically pure alpha-(fluoroalkyl)-beta-sulfinyl enamines has been achieved by aza-Wittig reaction of triphenyliminophosphoranes with the corresponding alpha-fluorinated-alpha'-sulfinyl ketones. The title compounds 3,4 showed an overwhelming preference for the Z stereochemistry of the enamine form. Their general reactivity has been studied. The reaction with some electrophiles (i.e. benzyl chloroformate and benzyl and allyl bromide) occurs at the nitrogen atom providing the corresponding N,N-disubstituted enamines. Nucleophiles add smoothly to C-2: heteroatom-centered nucleophiles like methanol, ammonia, and thiophenol afford gem-disubstituted derivatives under thermodynamic control, while a C-centered nucleophile like nitromethane adds in irreversible fashion. The hydride- and deuteride-promoted reduction of 3,4 to the N-Cbz-protected (14) and N-unprotected (15) alpha-fluorinated-alpha'-sulfinyl amines has been studied. Hydride addition was stereoselective, while low stereoselection was obtained with the other tested nucleophiles. Desulfurization of the optically pure 1,1,1-trifluoro-3-sulfinyl amine 15a afforded (R)-1-(trifluoromethyl)ethylamine 17. The Pummerer rearrangement of 14 occurs in an unusual nonoxidative way affording the sulfenamide 24, that readily provided (R)-(2-H)- and -(2-D)-3,3,3-trifluoroalaninol (19) and (R)-3,3,3-trifluoroalanine (22).

  DOI：

  10.1021/jo952097r

文献信息

• Diastereoselective Trifluoromethylation of Chiral<i>N</i>-(Tolylsulfinyl)imines in the Presence of Lewis Bases
  作者：Yoshikazu Kawano、Teruaki Mukaiyama

  DOI：10.1246/cl.2005.894

  日期：2005.7

  A diastereoselctive trifluoromethylation of chiral N-(tolylsulfinyl)imines with (trifluoromethyl)trimethylsilane in the presence of Lewis bases such as tetrabutylammonium acetate or phenoxide proceeded smoothly to afford the corresponding trifluoromethylated adducts in good yields.

  一种在路易斯碱（如四丁基铵乙酸盐或酚氧基）存在下，利用(trifluoromethyl)trimethylsilane对手性N-(托烯基亚磺酰)亚胺进行的非对映体选择性三氟甲基化反应顺利进行，产物获得了良好的产率。
• Asymmetric reduction of 2-(N-arylimino)-3,3,3-trifluoropropanoic acid esters leading to enantiomerically enriched 3,3,3-trifluoroalanine
  作者：Takashi Sakai、Fengyang Yan、Setsuo Kashino、Kenji Uneyama

  DOI：10.1016/0040-4020(95)00866-7

  日期：1996.1

  2-(N-arylimino)-3,3,3-trifluoropropanoic acid esters with a chiral oxazaborolidine catalyst and subsequent oxidative removal of N-aromatic moiety with retention of the configuration. Detailed optimization studies revealed that the effects of solvents, temperature, and the structural modification of the substrate were drastic on the enantioselectivity. The absolute configuration of 1 was determined to be (R) by

  对映体富集的3,3,3-三氟丙氨酸（1）（高达62％ee）已通过手性恶唑硼烷催化剂和2-（N-芳基氨基）-3,3,3-三氟丙酸酯的不对称还原和随后氧化除去N-芳族部分并保留构型。详细的优化研究表明，溶剂，温度和底物的结构改性对对映选择性的影响很大。通过相应的N-（S）-（+）-樟脑磺酰基衍生物的X射线晶体学分析确定1的绝对构型为（R）。
• Lewis acid activation of chiral 2-trifluoromethyl-1,3-oxazolidines. Application to the stereoselective synthesis of trifluoromethylated amines, α- and β-amino acids
  作者：Nicolas Lebouvier、Christophe Laroche、Florent Huguenot、Thierry Brigaud

  DOI：10.1016/s0040-4039(02)00330-1

  日期：2002.4

  The reaction of chiral 2-trifluoromethyl-1,3-oxazolidines with various silylated nucleophiles under Lewis acid activation provides a stereoselective route to functionalized α-trifluoromethylamines. This methodology was successfully applied to the diastereoselective synthesis of trifluoromethylated homoallylic and propargylic amines, trifluoromethylated α-amino nitrile, β-aminoketone and β-aminoester

  在路易斯酸活化下，手性2-三氟甲基-1,3-恶唑烷与各种甲硅烷基化的亲核试剂的反应为官能化的α-三氟甲基胺提供了立体选择途径。该方法成功地应用于三氟甲基化的均烯丙基和炔丙基胺，三氟甲基化的α-氨基腈，β-氨基酮和β-氨基酯的非对映选择性合成。将α-氨基腈和β-氨基酯一步一步转化为（+）-3,3,3-三氟丙氨酸和（+）-4,4,4,4-三氟-3-氨基丁酸。
• Facile and Stereoselective Synthesis of Non-Racemic 3,3,3-Trifluoroalanine
  作者：Marcello Crucianelli、Natalia Battista、Pierfrancesco Bravo、Alessandro Volonterio、Matteo Zanda

  DOI：10.3390/51201251

  日期：——

  A highly stereoselective enantiodivergent synthesis of non-racemic 3,3,3-trifluoroalanine 7 is reported. The methodology is based on the reduction, by 9-BBN or DIBAH, of the chiral sulfinimine 3 derived from ethyl trifluoropyruvate, followed by acidic hydrolysis of the resulting diastereomeric sulfinamides 4 and 5.

  报告了一种高度立体选择性的非外消旋 3,3,3-三氟丙氨酸 7 的对映发散合成方法。该方法基于用 9-BBN 或 DIBAH 还原由三氟丙酮酸乙酯得到的手性亚磺酰亚胺 3，然后对得到的非对映亚磺酰胺 4 和 5 进行酸性水解。
• Halogen substituted mercaptoacylamino acids
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04154935A1

  公开（公告）日：1979-05-15

  New halogen substituted mercaptoacylamino acids which have the general formula ##STR1## ARE USEFUL AS HYPOTENSIVE AGENTS.

  新的卤代硫醇酰胺酸，其通用式为##STR1##，可作为降压剂。