diethyl 2-acetamido-2-(1-nitro-4-phenylbutan-2-yl)malonate | 1556013-87-6

• 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-(1-nitro-4-phenylbutan-2-yl)malonate
• 英文别名: Diethyl 2-acetamido-2-(1-nitro-4-phenylbutan-2-yl)propanedioate；diethyl 2-acetamido-2-(1-nitro-4-phenylbutan-2-yl)propanedioate
• CAS: 1556013-87-6
• 化学式: C₁₉H₂₆N₂O₇
• 分子量: 394.425
• InChiKey: WHXCBBXZXCQZBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (4-硝基丁-3-烯基)苯 、 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 24.0h， 以88%的产率得到diethyl 2-acetamido-2-(1-nitro-4-phenylbutan-2-yl)malonate
  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

• 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.