(E)-ethyl 3-(2-(1-hydroxy-2-nitroethyl)phenyl)acrylate | 1446512-56-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-ethyl 3-(2-(1-hydroxy-2-nitroethyl)phenyl)acrylate
• CAS: 1446512-56-6
• 化学式: C₁₃H₁₅NO₅
• 分子量: 265.266
• InChiKey: IVVNVHVGYIYVTA-ABZNLYFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  89.67
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 3-(2-(1-hydroxy-2-nitroethyl)phenyl)acrylate 在 盐酸 、 锌 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以65%的产率得到ethyl 2-((4S)-1,2,3,4-tetrahydro-4-hydroxyisoquinolin-1-yl)acetate
  参考文献：
  名称：

  Asymmetric synthesis of 1,2,3-trisubstituted indanes via an enantioselective copper(II)-catalyzed asymmetric nitroaldol reaction followed by an intramolecular Michael cyclization

  摘要：

  Herein we describe a novel approach for the synthesis of a chiral 1,2,3-trisubstituted indane, a privileged substructure in medicinal chemistry, via an enantioselective nitroaldol reaction and subsequent intramolecular Michael addition. The asymmetric copper(II)-catalyzed reactions of ortho-formyl cinnamates, ortho-formyl cinnamonitrile, or ortho-formyl alpha-benzalketones with nitromethane were carried out using the C1-symmetric chiral secondary diamine L1 as a ligand, which afforded the nitroaldol products in high yields (up to 92%) and with good to excellent enantioselectivities (up to 97%) under mild conditions. The notable effect of the base and the dosage of nitromethane on the reaction are also discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.05.005
• 作为产物：
  描述：

  硝基甲烷 、 (E)-ethyl 3-(2-formylphenyl)acrylate 在 C₁₅H₂₈N₂ 、 copper(II) acetate monohydrate 、 N,N-二异丙基乙胺 、 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到(E)-ethyl 3-(2-(1-hydroxy-2-nitroethyl)phenyl)acrylate
  参考文献：
  名称：

  Asymmetric synthesis of 1,2,3-trisubstituted indanes via an enantioselective copper(II)-catalyzed asymmetric nitroaldol reaction followed by an intramolecular Michael cyclization

  摘要：

  Herein we describe a novel approach for the synthesis of a chiral 1,2,3-trisubstituted indane, a privileged substructure in medicinal chemistry, via an enantioselective nitroaldol reaction and subsequent intramolecular Michael addition. The asymmetric copper(II)-catalyzed reactions of ortho-formyl cinnamates, ortho-formyl cinnamonitrile, or ortho-formyl alpha-benzalketones with nitromethane were carried out using the C1-symmetric chiral secondary diamine L1 as a ligand, which afforded the nitroaldol products in high yields (up to 92%) and with good to excellent enantioselectivities (up to 97%) under mild conditions. The notable effect of the base and the dosage of nitromethane on the reaction are also discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.05.005