(+/-)-3-cyano-2-phenylpropionic acid | 442542-97-4

• 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: (+/-)-3-cyano-2-phenylpropionic acid
• 英文别名: 3-cyano-2-phenylpropanoic acid；3-cyano-2-phenylpropionic acid；α-phenyl-β-cyanopropionic acid；3-cyano-2-phenyl-propionic acid；3-Cyan-2-phenyl-propionsaeure
• CAS: 442542-97-4
• 化学式: C₁₀H₉NO₂
• mdl: MFCD20638748
• 分子量: 175.187
• InChiKey: XBZQKMPPVQSLHI-UHFFFAOYSA-N

物化性质

• 熔点：
  97 °C(Solv: benzene (71-43-2))
• 沸点：
  365.4±30.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

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：

  (+/-)-3-cyano-2-phenylpropionic acid 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 20.0 ℃ 、275.8 kPa 条件下， 反应 72.0h， 以99%的产率得到4-氨基-2-苯基丁酸
  参考文献：
  名称：

  γ-氨基酸的有效合成并尝试驱动其对映选择性。

  摘要：

  将羧酸双阴离子与溴乙腈铅加成，以良好的收率生成相应的γ-氰酸，其在氢化后产生γ-氨基酸。此两步方法改进了先前描述的结果。ee 的差是由于我们尝试通过手性酰胺诱导来驱动这种转化的对映选择性。

  DOI：

  10.3390/molecules13040716
• 作为产物：
  描述：

  (3R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 3-cyano-2-phenylpropionate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (+/-)-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

• Practical Synthesis of Diethyl Phenylsuccinate by Mg-promoted Carboxylation of Ethyl Cinnamate
  作者：Hirofumi Maekawa、Taro Murakami、Takeshi Miyazaki、Ikuzo Nishiguchi

  DOI：10.1246/cl.2011.368

  日期：2011.4.5

  Mg-promoted reduction of ethyl cinnamate (1a) in the presence of carbon dioxide gave a mixture of β-carboxylated compound 2a and α,β-dicarboxylated compound 3a. Similar reductive carboxylation of 1...

  在二氧化碳存在下，Mg 促进肉桂酸乙酯 (1a) 的还原得到 β-羧化化合物 2a 和 α,β-二羧化化合物 3a 的混合物。1的类似还原羧化...
• Electrochemical Reduction of Cinnamonitrile in the Presence of Carbon Dioxide: Synthesis of Cyano- and Phenyl-Substituted Propionic Acids
  作者：Huan Wang、Mei-Yu Lin、Kai Zhang、Su-Jiao Li、Jia-Xing Lu

  DOI：10.1071/ch08092

  日期：——

  Cyano- and phenyl-substituted propionic acids were synthesized simply and efficiently by electrocarboxylation of cinnamonitrile in undivided cells using the non-noble metal nickel as cathode and magnesium as the anode. The radical anion generated by the electroreduction of cinnamonitrile in the absence of CO2 is involved in several competitive reactions that lead to the formation of linear hydrodimers, cyclic hydrodimers, saturated dihydro products, and glutaronitrile derivatives. While under 101.325 kPa of CO2, the electrocarboxylation could easily be carried out in the absence of additional catalysts, and with good yield (84.8%). The influence of various synthetic parameters, such as the nature of the electrode, the working potential, the concentration, and the temperature, on the electrocarboxylation reaction was investigated.

  在以非贵金属镍为阴极、镁为阳极的非分裂电池中，通过对肉桂腈进行电羧化，简单而高效地合成了氰基和苯基取代的丙酸。在没有二氧化碳的情况下，肉桂腈电还原产生的自由基阴离子参与了几个竞争反应，从而形成线性氢二聚体、环状氢二聚体、饱和二氢产物和戊二腈衍生物。在二氧化碳压力为 101.325 千帕的条件下，电羧化反应可以在不使用额外催化剂的情况下轻松进行，而且产率很高（84.8%）。研究还探讨了电极性质、工作电位、浓度和温度等各种合成参数对电羧化反应的影响。
• ANTIVIRAL AGENTS
  申请人：Kumar V. Dange

  公开号：US20070287699A1

  公开（公告）日：2007-12-13

  Compounds are provided having utility for the treatment of viral infections, particularly HCV.

  提供了化合物，可用于治疗病毒感染，尤其是HCV。
• Tetrahydroquinoline derivatives useful for neurodegenerative disorders
  申请人：MERCK SHARP & DOHME LTD.

  公开号：EP0386839A2

  公开（公告）日：1990-09-12

  A class of 1,2,3,4-tetrahydroquinolines possessing at least one substituent, or a spirocyclic moiety, at the 4-position, and an acidic group or a group convertible thereto in vivo at the 2-position, are specific antagonists of N-methyl-D-aspartate (NMDA) receptors and are therefore useful in the treatment and/or prevention of neurodegenerative disorders..

  一类1,2,3,4-四氢喹啉类化合物在4-位上具有至少一个取代基或螺环分子，在2-位上具有酸性基团或在体内可转化的基团，是N-甲基-D-天冬氨酸（NMDA）受体的特异性拮抗剂，因此可用于治疗和/或预防神经退行性疾病。
• A simple synthesis of γ-aminoacids
  作者：Salvador Gil、Margarita Parra、Pablo Rodríguez

  DOI：10.1016/j.tetlet.2007.03.037

  日期：2007.5

  The addition of dianions of carboxylic acids to bromoacetonitrile, leads, in good yields, to the corresponding gamma-cyanoacids that give gamma-aminoacids on hydrogenation. This two-step methodology improves the results previously described. (c) 2007 Elsevier Ltd. All rights reserved.

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