diethyl 2-acetamido-2-[(1S)-1-(3-methoxyphenyl)-2-nitroethyl]propanedioate

• 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: diethyl 2-acetamido-2-[(1S)-1-(3-methoxyphenyl)-2-nitroethyl]propanedioate
• 化学式: C₁₈H₂₄N₂O₈
• 分子量: 396.397
• InChiKey: CHVQKFAYYGUJSI-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-methoxy-3-(2-nitro-vinyl)-benzene 、 乙酰氨基丙二酸二乙酯 在 Methyl-4,6-O-benzylidene-2,3-dideoxy-α-D-glucopyranosido[2,3-h]-N-3-hydroxypropyl-1,4,7,10-tetraoxa-13-azacyclopentadecane 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 以34%的产率得到
  参考文献：
  名称：

  Enantioselective Michael addition of malonates to aromatic nitroalkenes catalyzed by monosaccharide-based chiral crown ethers

  摘要：

  The asymmetric Michael addition of diethyl malonate and alpha-substituted diethyl malonates to aromatic nitroalkenes was carried out under mild reaction conditions in a solid-liquid phase transfer reaction in the presence of alpha-D-glucopyranoside- and alpha-D-mannopyranoside-based crown ethers as the catalysts. The use of D-glucose-based lariat ether 1 gave the best results. The substituents of the beta-nitrostyrene and the diethyl malonate had a significant impact on the chemical yields and enantioselectivity. The addition of diethyl-2-acetamidomalonate to aromatic nitroalkenes afforded the corresponding Michael adducts in moderate to high enantiomeric excess (ee up to 99%). The reaction of diethyl-2-methylmalonate with 2-nitro-beta-nitrostyrene gave the adduct with 93% enantiomeric excess in the presence of crown catalyst 1. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.12.007

文献信息

• Asymmetric C–C bond formation via Darzens condensation and Michael addition using monosaccharide-based chiral crown ethers
  作者：Péter Bakó、Zsolt Rapi、György Keglevich、Tamás Szabó、Péter L. Sóti、Tamás Vígh、Alajos Grűn、Tamás Holczbauer

  DOI：10.1016/j.tetlet.2011.01.094

  日期：2011.3

  phase asymmetric Darzens condensations were promoted by d-glucose- and d-mannose-based crown ethers. The corresponding aromatic and heteroaromatic α,β-epoxyketones were obtained with moderate to high enantioselectivities (up to 96%) as well as diastereoselectivities (up to 98:2) under mild reaction conditions. The absolute configurations of several of the epoxyketones were determined by single crystal

  d-葡萄糖和d-甘露糖基冠醚促进了液相-液相不对称Darzens缩合反应。在温和的反应条件下，获得了具有中等至高对映选择性（最高96％）以及非对映选择性（最高98：2）的相应芳族和杂芳族α，β-环氧酮。通过单晶X射线分析确定几种环氧酮的绝对构型。乙酰氨基丙二酸二乙酯在反式-β-硝基烯烃中的迈克尔加成反应是在固-液两相系统中，在以d-葡萄糖为基础的冠状催化剂存在下，ee高达99％。
• Enantioselective Michael addition of malonates to aromatic nitroalkenes catalyzed by monosaccharide-based chiral crown ethers
  作者：Zsolt Rapi、Balázs Démuth、György Keglevich、Alajos Grűn、László Drahos、Péter L. Sóti、Péter Bakó

  DOI：10.1016/j.tetasy.2013.12.007

  日期：2014.1

  The asymmetric Michael addition of diethyl malonate and alpha-substituted diethyl malonates to aromatic nitroalkenes was carried out under mild reaction conditions in a solid-liquid phase transfer reaction in the presence of alpha-D-glucopyranoside- and alpha-D-mannopyranoside-based crown ethers as the catalysts. The use of D-glucose-based lariat ether 1 gave the best results. The substituents of the beta-nitrostyrene and the diethyl malonate had a significant impact on the chemical yields and enantioselectivity. The addition of diethyl-2-acetamidomalonate to aromatic nitroalkenes afforded the corresponding Michael adducts in moderate to high enantiomeric excess (ee up to 99%). The reaction of diethyl-2-methylmalonate with 2-nitro-beta-nitrostyrene gave the adduct with 93% enantiomeric excess in the presence of crown catalyst 1. (C) 2013 Elsevier Ltd. All rights reserved.