(S)-4-fluoro-N-benzoyl-phenylalanine methylester | 143051-64-3

• 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: (S)-4-fluoro-N-benzoyl-phenylalanine methylester
• 英文别名: methyl (2S)-2-benzamido-3-(4-fluorophenyl)propanoate
• CAS: 143051-64-3
• 化学式: C₁₇H₁₆FNO₃
• 分子量: 301.317
• InChiKey: YQYWKWRQZUBMSB-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (Z)-2-Benzoylamino-3-(4-fluoro-phenyl)-acrylic acid methyl ester 在 {Rh[(S)-Xyl-BDPAB]}BF₄ 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 0.17h， 生成 (S)-4-fluoro-N-benzoyl-phenylalanine methylester
  参考文献：
  名称：

  铑催化衍生自1,1'-联萘-2,2'-二胺的氨基膦配体

  摘要：

  通过1,1反应合成手性配体2,2'-双（二环己基膦氨基）-1,1'-联萘基和2,2'-双[双（3,5-二甲基苯基）膦氨基] -1,1'-联萘基′-联萘-2，2′-二胺分别与二环己基氯膦和双（3，5-二甲基苯基）氯膦。这些配体在Rh催化的各种酰胺基丙烯酸和酯的不对称加氢中的应用提供了具有出色对映选择性（高达99％ee和定量收率）的手性氨基酸衍生物。

  DOI：

  10.1016/s0040-4039(02)01510-1

文献信息

• Rhodium-catalyzed asymmetric hydrogenation with aminophosphine ligands derived from 1,1′-binaphthyl-2,2′-diamine
  作者：Rongwei Guo、Xingshu Li、Jing Wu、Wai Him Kwok、Jian Chen、Michael C.K Choi、Albert S.C Chan

  DOI：10.1016/s0040-4039(02)01510-1

  日期：2002.9

  Chiral ligands 2,2′-bis(dicyclohexylphosphinoamino)-1,1′-binaphthyl and 2,2′-bis[bis(3,5-dimethylphenyl)phosphinoamino]-1,1′-binaphthyl were synthesized by reacting 1,1′-binaphthyl-2,2′-diamine with dicyclohexylchlorophosphine and bis(3,5-dimethylphenyl)chlorophosphine, respectively. Application of these ligands to the Rh-catalyzed asymmetric hydrogenation of a variety of amidoacrylic acids and esters

  通过1,1反应合成手性配体2,2'-双（二环己基膦氨基）-1,1'-联萘基和2,2'-双[双（3,5-二甲基苯基）膦氨基] -1,1'-联萘基′-联萘-2，2′-二胺分别与二环己基氯膦和双（3，5-二甲基苯基）氯膦。这些配体在Rh催化的各种酰胺基丙烯酸和酯的不对称加氢中的应用提供了具有出色对映选择性（高达99％ee和定量收率）的手性氨基酸衍生物。
• A new type of chiral-pyridoxamines for catalytic asymmetric transamination of α-keto acids
  作者：Jianfeng Chen、Junyu Zhao、Xing Gong、Dongfang Xu、Baoguo Zhao

  DOI：10.1016/j.tetlet.2016.09.005

  日期：2016.10

  A new type of chiral pyridoxamines bearing an adjacent chiral stereocenter has been developed via multi-step synthesis. The pyridoxamines displayed catalytic activity in asymmetric transamination of α-keto acids to give a variety of optically active amino acids in 27–78% yields with 34–62% ee’s under very mild conditions. This work provides a synthetic strategy to construct new chiral pyridoxamines

  通过多步合成已经开发了一种新型的带有相邻手性立体中心的手性吡ido胺。吡ido胺在非常温和的条件下，在α-酮酸的不对称转氨反应中显示出催化活性，从而以27-78％的产率提供了34-62％ee的多种光学活性氨基酸。这项工作提供了使用溴吡啶7作为关键合成子来构建新的手性吡ido胺的合成策略，也代表了手性吡x胺在不对称催化中的早期应用实例。
• A comparison of the asymmetric hydrogenation catalyzed by rhodium complexes containing chiral ligands with a binaphthyl unit and those with a 5,5′,6,6′,7,7′,8,8′-octahydro-binaphthyl unit
  作者：Fu-Yao Zhang、Wai Him Kwok、Albert S.C. Chan

  DOI：10.1016/s0957-4166(01)00399-8

  日期：2001.9

  The chiral ligands H8–BINAPO and H8–BDPAB were synthesized by reacting chlorodiphenylphosphine with H8–BINOL and H8–BINAM, respectively. Applications of these ligands in the Rh-catalyzed enantioselective hydrogenation of a variety of (Z)-acetamido-3-arylacrylic acid methyl esters provided chiral amino acid derivatives with good to excellent enantioselectivities (H8–BINAPO: up to 84.0% e.e.; H8–BDPAB:

  通过使氯二苯基膦分别与H 8 -BINOL和H 8 -BINAM反应合成手性配体H 8 -BINAPO和H 8 -BDPAB 。这些配体在多种（Z）-乙酰氨基-3-芳基丙烯酸甲酯的Rh催化对映选择性氢化中的应用提供了具有良好至优异对映选择性的手性氨基酸衍生物（H 8 -BINAPO：高达84.0％ee; H 8 –BDPAB：ee高达97.1％）。在乙酰胺基丙烯酸的氢化中，当使用[Rh（H 8 -BDPAB）] +催化剂时，获得了99％ee 。[Rh（H 8）的催化活性和对映选择性-BINAPO）] +和[Rh（H 8 -BDPAB）] +明显优于使用相应的含BINAPO（最高64％ee）和BDPAB（最高92.6％ee）的铑催化剂获得的那些。
• Unusual amino acids
  作者：Hans-Walter Krause、Hans-Jörn Kreuzfeld、Christian Döbler

  DOI：10.1016/s0957-4166(00)80262-1

  日期：1992.4

  Few (Z)-alpha-N-benzoylamino-beta-(fluorophenyl)-acrylic acids and their esters were prepared by known procedures and hydrogenated to the corresponding optically active alpha-benzoyl-beta-(fluorophenyl)-alanine derivatives with optical yields up to 90% using the rhodium complexes of "PROPRAPHOS" and O,N-bis(diphenylphosphino)-2-exo-hydroxy, 3-endo-methylamino-norbornane as chiral catalysts. The method proved to be apt for upscaling the preparation. Deacylation of the obtained amino acids gave the hydrochlorides of the fluorinated phenylalanines in very pure state.
• The synthesis of new chiral phosphine–phosphinites, phosphine–phosphoramidite, and phosphine–phosphite ligands and their applications in asymmetric hydrogenation
  作者：Xian Jia、Xingshu Li、Wing Sze Lam、Stanton H.L Kok、Lijin Xu、Gui Lu、Chi-Hung Yeung、Albert S.C Chan

  DOI：10.1016/j.tetasy.2004.05.046

  日期：2004.7

  New chiral phosphine-phosphinite, phosphine–phosphoramidite ligands and phosphine–phosphite 1a, 1b, 2 and 3 have been synthesized and examined in the enantioselective hydrogenation of dehydroamino acid derivatives and α-aryl enamides. The results demonstrate that both rhodium-1b and rhodium-2 complexes were highly efficient catalysts in asymmetric hydrogenation reactions (up to 99.6% ee was obtained)

  合成了新的手性膦-亚膦酸酯，膦-亚磷酰胺配体和膦-亚磷酸酯1a，1b，2和3，并在脱氢氨基酸衍生物和α-芳基酰胺的对映选择性加氢中进行了研究。结果表明，铑-1b和铑-2络合物都是不对称氢化反应中的高效催化剂（获得高达99.6％ee）。