(2S,4R)-4-羟基吡咯烷-2-羧酸((S)-1-苯乙基)酰胺 | 1032574-48-3

• 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
• 中文名称: (2S,4R)-4-羟基吡咯烷-2-羧酸((S)-1-苯乙基)酰胺
• 英文名称: (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid ((S)-1-phenylethyl)amide
• 英文别名: (2S,4R)-4-hydroxy-N-((S)-1-phenylethyl)pyrrolidine-2-carboxamide；trans-4-hydroxy-N-((S)-1-phenylethyl)pyrrolidine-2-carboxamide；trans-4-hydroxy-(L)-prolinamide；N-[(2s,4r)-4-hydroxyprolyl]-(s)-1-phenylethylamine；(2S,4R)-4-hydroxy-N-[(1S)-1-phenylethyl]pyrrolidine-2-carboxamide
• CAS: 1032574-48-3
• 化学式: C₁₃H₁₈N₂O₂
• 分子量: 234.298
• InChiKey: MGNKVDGSPPZYJV-WCQGTBRESA-N

物化性质

• 熔点：
  161-164 °C(Solvent: Diethyl ether ; Ligroine)
• 沸点：
  485.8±45.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  61.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2S,4R)-1-(叔丁氧羰基)-4-((叔丁基二甲基甲硅烷基)氧基)吡咯烷-2-羧酸 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 37.0h， 生成 (2S,4R)-4-羟基吡咯烷-2-羧酸((S)-1-苯乙基)酰胺
  参考文献：
  名称：

  醛与硝基烯烃不对称迈克尔加成反应中简单的4-羟基脯氨酰胺有机催化剂的结构反应性研究

  摘要：

  合成了一系列简单的4-羟基脯氨酰胺，发现它们可以作为有机催化剂，以极高的收率（98％），全非对映选择性（99：1，syn：anti）和对映选择性（98）将醛不对称共轭加成至硝基烯烃。％ee，代表syn）。此外，实现了低催化剂负载量（5mol％）和低醛摩尔过量（1.5当量）的使用。

  DOI：

  10.1002/adsc.201100028
• 作为试剂：
  描述：

  5,7-二溴靛红 、 丙酮 在 (2S,4R)-4-羟基吡咯烷-2-羧酸((S)-1-苯乙基)酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 48.17h， 以51%的产率得到
  参考文献：
  名称：

  trans-4-Hydroxy-l-prolinamide as an efficient catalyst for direct asymmetric aldol reaction of acetone with isatins

  摘要：

  Prolinamide (2S,4R)-4-hydroxy-N-((S)-1-phenylethyl)pyrrolidine-2-carboxamide was found to be an efficient organocatalyst (10 mol %) for the direct asymmetric aldol reactions of isatins with acetone at -35 degrees C in THF and afforded the product in 79% yield with 74% ee. We have generalised the methodology for the direct asymmetric aldol reaction between isatin derivatives and acetone, and the corresponding aldol products were obtained in high yields (up to 99%) and with moderate enantioselectivities (up to 80%). This method has been applied to the enantioselective synthesis of (S)-convolutamydine. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.04.008

文献信息

• An Enantioselective Biginelli Reaction Catalyzed by a Simple Chiral Secondary Amine and Achiral Brønsted Acid by a Dual-Activation Route
  作者：Junguo Xin、Lu Chang、Zongrui Hou、Deju Shang、Xiaohua Liu、Xiaoming Feng

  DOI：10.1002/chem.200701581

  日期：2008.3.27

  An enantioselective Biginelli reaction that proceeds by a dual-activation route has been developed by using a combined catalyst of a readily available trans-4-hydroxyproline-derived secondary amine and a Bronsted acid. Aromatic, heteroaromatic, and fused-ring aldehydes were found to be suitable substrates for this multicomponent reaction. The corresponding dihydropyrimidines were obtained in moderate-to-good

  通过使用容易获得的反式4-羟基脯氨酸衍生的仲胺和布朗斯台德酸的组合催化剂，已经开发了通过双活化途径进行的对映选择性比吉内利反应。发现芳族，杂芳族和稠环醛是该多组分反应的合适底物。在温和条件下，以中等至良好的收率获得了相应的二氢嘧啶，收率高达98％ee。根据实验结果和观察到的产物的绝对构型，提出了一个合理的过渡态来解释激活和不对称诱导的起源。
• Direct asymmetric aldol reactions catalysed by trans-4-hydroxy-(S)-prolinamide in solvent-free conditions
  作者：Geeta Devi Yadav、Surendra Singh

  DOI：10.1016/j.tetasy.2015.09.003

  日期：2015.11

  Direct asymmetric aldol reactions between 4-nitrobenzaldehyde and cyclohexanone were catalysed by trans-4-hydroxy-(S)-prolinamide (10 mol %) in the presence of CH3COOH (10 mol %) as the co-catalyst under solvent-free conditions at 15 degrees C. (2S,4R)-4-Hydroxy-N-((S)-1-phenylethyl)pyrrolidine-2-carboxamide 2 efficiently, catalysed the asymmetric aldol reaction to afford the product in >99% yield and with 95% ee with an antilsyn ratio of 88:12 after 18 h. The additional trans-hydroxyl group on (S)-prolinamide and (S)-1-phenylethylamine both influenced the ee of the predominant anti aldol product. Different benzaldehyde derivatives with cyclohexanone gave the corresponding aldol products in 38-89% yields and with 56-94% ee with antilsyn (100:0-71:29). Catalyst 2 can be used up to 5 continuous cycles for asymmetric aldol reactions between 4-nitrobenzaldehyde and cyclohexanone with overall 91% yield and 86% yield of anti-product with anti/syn (98:2). (C) 2015 Elsevier Ltd. All rights reserved.