(R)-3-cyano-2-phenylpropionic acid | 674776-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3-cyano-2-phenylpropionic acid
• 英文别名: (R)-α-phenyl-β-cyanopropionic acid；(2R)-3-cyano-2-phenylpropanoic acid
• CAS: 674776-40-0
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: XBZQKMPPVQSLHI-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-cyano-2-phenylpropionic acid 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 1,4-二氧六环 、 水 、 溶剂黄146 为溶剂， 20.0 ℃ 、405.3 kPa 条件下， 反应 36.0h， 生成 (R)-4-(tert-butoxycarbonylamino)-2-phenylbutanoic acid
  参考文献：
  名称：

  Stereoselective synthesis of both enantiomers of N-Boc-α-aryl-γ-aminobutyric acids

  摘要：

  Esterification of racemic alpha-aryl-beta-cyanopropionic acid chlorides with either (R)- or (S)-N-phenylpantolactam as the chiral auxiliary in the presence of Et3N resulted in the predominant formation of (alphaR,3'R)- or (alphaS,3'S)-configured pantolactam cyano ester, respectively, in nearly quantitative yields with diastereomeric ratios of up to 93:7. Column chromatography of the diastereoenriched cyano esters, followed by hydrolysis of the resulting diastereopure cyano esters under essentially nonracemizing conditions gave enantiopure alpha-aryl-beta-cyanopropionic acids, which were readily converted in high yields into enantiopure (OER)- and (alphaS)-configured N-tert-butoxycarbonyl-alpha-aryl-gamma-aminobutyric acid (GABA) derivatives of potential biological interest. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.035
• 作为产物：
  描述：

  (3R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 3-cyano-2-phenylpropionate 在 lithium hydroxide 、 3 A molecular sieve 、 五氯化磷 、 双氧水 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 水 为溶剂， 反应 8.5h， 生成 (R)-3-cyano-2-phenylpropionic acid
  参考文献：
  名称：

  Stereoselective synthesis of both enantiomers of N-Boc-α-aryl-γ-aminobutyric acids

  摘要：

  Esterification of racemic alpha-aryl-beta-cyanopropionic acid chlorides with either (R)- or (S)-N-phenylpantolactam as the chiral auxiliary in the presence of Et3N resulted in the predominant formation of (alphaR,3'R)- or (alphaS,3'S)-configured pantolactam cyano ester, respectively, in nearly quantitative yields with diastereomeric ratios of up to 93:7. Column chromatography of the diastereoenriched cyano esters, followed by hydrolysis of the resulting diastereopure cyano esters under essentially nonracemizing conditions gave enantiopure alpha-aryl-beta-cyanopropionic acids, which were readily converted in high yields into enantiopure (OER)- and (alphaS)-configured N-tert-butoxycarbonyl-alpha-aryl-gamma-aminobutyric acid (GABA) derivatives of potential biological interest. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.035

文献信息

• Nitrilase Activity Screening on Structurally Diverse Substrates: Providing Biocatalytic Tools for Organic Synthesis
  作者：Carine Vergne-Vaxelaire、Franck Bordier、Aurélie Fossey、Marielle Besnard-Gonnet、Adrien Debard、Aline Mariage、Virginie Pellouin、Alain Perret、Jean-Louis Petit、Mark Stam、Marcel Salanoubat、Jean Weissenbach、Véronique De Berardinis、Anne Zaparucha

  DOI：10.1002/adsc.201201098

  日期：2013.6.17

  carboxylic acid building blocks, a β‐substituted phenylpropanoic acid, a cyclic γ‐keto carboxylic acid and a mononitrile monocarboxylic acid, were achieved from the corresponding nitrile substrates, using three new nitrilases (two from Sphingomonas wittichii and one from Syntrophobacter fumaroxidans). Improvements of nitrilase activities through the optimization of reaction parameters and the preparative

  针对25种结构多样的底物进行高通量的候选腈水解酶筛选，使我们能够创建125种经过实验验证的腈水解酶的广泛集合。通过基因组方法从700种多样的原核物种和一个作为亚硝化酶家族多样性代表的元基因组中选择了这些酶。通过提供大量经过测试的腈水解酶及其指定的底物，该酶标物的酶促筛选扩展了用于化学合成的生物催化工具箱。三个例子说明了我们酶的合成潜力。使用三个新的腈水解酶（其中两个来自腈水解酶）从相应的腈底物上合成了羧酸结构单元，β-取代的苯基丙酸，环状的γ-酮基羧酸和单腈一元羧酸Sphingomonas wittichii和一种来自Sumtrophobacter fumaroxidans的细菌。通过这三个实例，通过优化反应参数和制备型生物催化合成方法改善了腈水解酶的活性。
• Stereoselective synthesis of both enantiomers of N-Boc-α-aryl-γ-aminobutyric acids
  作者：Pelayo Camps、Diego Muñoz-Torrero、Laura Sánchez

  DOI：10.1016/j.tetasy.2003.10.035

  日期：2004.1

  Esterification of racemic alpha-aryl-beta-cyanopropionic acid chlorides with either (R)- or (S)-N-phenylpantolactam as the chiral auxiliary in the presence of Et3N resulted in the predominant formation of (alphaR,3'R)- or (alphaS,3'S)-configured pantolactam cyano ester, respectively, in nearly quantitative yields with diastereomeric ratios of up to 93:7. Column chromatography of the diastereoenriched cyano esters, followed by hydrolysis of the resulting diastereopure cyano esters under essentially nonracemizing conditions gave enantiopure alpha-aryl-beta-cyanopropionic acids, which were readily converted in high yields into enantiopure (OER)- and (alphaS)-configured N-tert-butoxycarbonyl-alpha-aryl-gamma-aminobutyric acid (GABA) derivatives of potential biological interest. (C) 2003 Elsevier Ltd. All rights reserved.