(S)-ethyl 2-(4-methoxyphenylamino)-4-oxo-4-(2-oxooxazolidin-3-yl)butanoate

• 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)-ethyl 2-(4-methoxyphenylamino)-4-oxo-4-(2-oxooxazolidin-3-yl)butanoate
• 英文别名: ethyl (2S)-2-(4-methoxyanilino)-4-oxo-4-(2-oxo-1,3-oxazolidin-3-yl)butanoate
• 化学式: C₁₆H₂₀N₂O₆
• 分子量: 336.345
• InChiKey: BKCIKIOAMVCDJZ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  甲氧苯胺 、 3-[(E)-3-(ethoxycarbonyl)propenoyl]-2-oxazolidinone 在 iodido(R-binaphtholato)samarium 作用下， 以 二氯甲烷 为溶剂， 反应 18.17h， 生成 (R)-ethyl 2-(4-methoxyphenylamino)-4-oxo-4-(2-oxooxazolidin-3-yl)butanoate 、 (S)-ethyl 2-(4-methoxyphenylamino)-4-oxo-4-(2-oxooxazolidin-3-yl)butanoate
  参考文献：
  名称：

  碘（联萘）钐催化芳香胺与N-链烯酰基恶唑烷酮的对映选择性共轭加成反应

  摘要：

  碘（联萘）钐催化芳香胺与 N-链烯酰恶唑烷酮的迈克尔加成反应，提供对映体过量高达 88% 的 β-氨基酸衍生物。对温度对不对称诱导的影响的研究揭示了两个反应中的同相转化。非线性效应的观察表明包括二聚体在内的几种活性物质之间存在平衡。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008）

  DOI：

  10.1002/ejoc.200700861

文献信息

• Samarium Iodobinaphtholate: An Efficient Catalyst for Enantioselective Aza-Michael Additions of O-Benzylhydroxylamine to N-Alkenoyloxazolidinones
  作者：Dorian Didier、Abdelkrim Meddour、Sophie Bezzenine-Lafollée、Jacqueline Collin

  DOI：10.1002/ejoc.201100041

  日期：2011.5

  Samarium diiodide is an efficient catalyst for the aza-Michael addition of O-benzylhydroxylamine to α,β-unsaturated N-acyloxazolidinones leading to mixtures of the Michael adduct and the product resulting from its amidation. Samarium iodobinaphtholate catalyzed reactions selectively afford the Michael adducts with enantiomeric excesses up to 88 %. An isoinversion effect with temperature is observed

  二碘化钐是一种有效的催化剂，用于将 O-苄基羟胺与 α,β-不饱和 N-酰基恶唑烷酮进行氮杂-迈克尔加成，从而形成迈克尔加合物及其酰胺化产物的混合物。碘联萘酸钐催化的反应选择性地提供对映体过量高达 88% 的迈克尔加合物。在 -40 °C 时观察到对映体过量最高的温度的同位倒置效应。
• Insight into the structure of the precatalyst and active species for samarium iodo binaphtholate catalysed aminolysis of epoxides
  作者：Myriam Martin、Sophie Bezzenine、Jacqueline Collin

  DOI：10.1016/j.tetasy.2010.04.035

  日期：2010.7

  Samarium iodo binaphtholate is an efficient Lewis acid catalyst for the enantioselective carbon-nitrogen bond formation such as aza-Michael reactions and the aminolysis of epoxides allowing highly enantioenriched aminoalcohols and aminoacids building blocks to be prepared. Various studies including the relationship between enantiomeric excess and temperature and observation of non linear effects for these reactions indicate the importance of the amine for the formation of the catalytic species. Results support the proposal of dimeric or more aggregated structures for samarium iodo binaphtholate and of a bimetallic active species for the aminolysis of epoxides. (C) 2010 Elsevier Ltd. All rights reserved.
• Enantioselective aza-Michael reactions catalyzed by samarium iodobinaphtholate
  作者：Iréna Reboule、Richard Gil、Jacqueline Collin

  DOI：10.1016/j.tetasy.2005.10.022

  日期：2005.11

  Samarium iodobinaphtholate is an efficient enantioselective catalyst for the Michael addition of aromatic amines to fumaryl oxazolidinone affording aspartic acid derivatives in good yields. Influence of temperature on the addition of p-anisidine revealed an isoinversion effect with the maximum enantiomeric excess of 88% at -40 degrees C. (c) 2005 Elsevier Ltd. All rights reserved.
• Enantioselective Conjugate Addition of Aromatic Amines toN-Alkenoyloxazolidinones Catalyzed by Iodido(binaphtholato)samarium
  作者：Iréna Reboule、Richard Gil、Jacqueline Collin

  DOI：10.1002/ejoc.200700861

  日期：2008.1

  Iodido(binaphtholato)samarium catalyzes the Michael addition of aromatic amines to N-alkenoyloxazolidinones affording β-amino acid derivatives with enantiomeric excesses of up to 88 %. A study of the effect of temperature on the asymmetric induction revealed an isoinversion in two reactions. The observation of a non-linear effect suggests an equilibrium between several active species including dimers

  碘（联萘）钐催化芳香胺与 N-链烯酰恶唑烷酮的迈克尔加成反应，提供对映体过量高达 88% 的 β-氨基酸衍生物。对温度对不对称诱导的影响的研究揭示了两个反应中的同相转化。非线性效应的观察表明包括二聚体在内的几种活性物质之间存在平衡。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008）