(1R,2S,3S)-2-(3-hydroxy-2-nitroindan-1-yl)-1-phenylethanone | 1446512-63-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,3S)-2-(3-hydroxy-2-nitroindan-1-yl)-1-phenylethanone
• 英文别名: 2-[(1R,2S,3S)-3-hydroxy-2-nitro-2,3-dihydro-1H-inden-1-yl]-1-phenylethanone
• CAS: 1446512-63-5
• 化学式: C₁₇H₁₅NO₄
• 分子量: 297.31
• InChiKey: LAELLHQBJQIOSU-PVAVHDDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  硝基甲烷 、 ortho-formyl chalcone 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 、 硝基甲烷 为溶剂， 反应 60.0h， 以58%的产率得到
  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