(S)-3-amino-1-(nitromethyl)-1H-benzo[f]chromene-2-carbonitrile | 1384291-09-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: (S)-3-amino-1-(nitromethyl)-1H-benzo[f]chromene-2-carbonitrile
• 英文别名: (S)-3-amino-1-nitromethyl-1H-benzo[f]chromene-2-carbonitrile；3-amino-1-(nitromethyl)-1H-benzo[f]chromene-2-carbonitrile
• CAS: 1384291-09-1
• 化学式: C₁₅H₁₁N₃O₃
• 分子量: 281.271
• InChiKey: LAZWRRAICYFEAU-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  102.18
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1-((E)-2-nitrovinyl)-2-naphthol 、 丙二腈 在 N-((S)-3-methyl-1-(piperidin-1-yl)butan-2-yl)-N'-((S)-3-(methyl-1-(piperidin-1-yl)butan-2-yl)propan-2-yl)-P-phenylphosphonothioic diamide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以84%的产率得到(S)-3-amino-1-(nitromethyl)-1H-benzo[f]chromene-2-carbonitrile
  参考文献：
  名称：

  Novel thiophosphonodiamides as efficient hydrogen bond donor catalysts in tandem Michael addition–cyclization of malononitrile and 2-(E)-2-nitrovinylphenols

  摘要：

  From L-amino acid, three chiral thiophosphonodiamides were prepared as new hydrogen bond donor organocatalysts. Under the mediation of the catalyst derived from L-valine, a tandem Michael addition/cyclization reaction between (E)-2-(2-nitrovinyl)phenols and malononitrile proceeds smoothly, giving pharmaceutically valuable 2-amino-4H-chromene-3-carbonitriles in high yields with 66-95% ee within 2 h. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.099

文献信息

• Enantioselective synthesis of 2-amino-4-(nitromethyl)-4<i>H</i>-chromene-3-carbonitriles from 2-iminochromenes
  作者：Gamze Koz、Omer Koz、Necdet Coskun

  DOI：10.1080/00397911.2016.1177728

  日期：2016.5.18

  ABSTRACT A series of medicinally important 2-amino-4-(nitromethyl)-4H-chromene-3-carbonitriles were synthesized using enantioselective conjugate addition of nitromethane to 2-iminochromenes. The reactions were performed using L8-Cu (II) catalytic system and moderate to good enantioselectivities (62–88%) and yields (66–96%) were obtained. GRAPHICAL ABSTRACT

  摘要 利用硝基甲烷与 2-亚氨基色烯的对映选择性共轭加成，合成了一系列具有药用价值的 2-氨基-4-(硝基甲基)-4H-色烯-3-腈。使用 L8-Cu (II) 催化体系进行反应，获得了中等至良好的对映选择性 (62-88%) 和产率 (66-96%)。图形概要
• Chiral bifunctional squaramide catalyzed asymmetric tandem Michael-cyclization reaction: efficient synthesis of optically active 2-amino-4H-chromene-3-carbonitrile derivatives
  作者：Keling Hu、Aidang Lu、Youming Wang、Zhenghong Zhou、Chuchi Tang

  DOI：10.1016/j.tetasy.2013.07.010

  日期：2013.8

  We have developed an efficient bifunctional squaramide catalyst for the asymmetric tandem Michael addition-cyclization of malononitrile to functionalized nitroolefins. This organocatalytic asymmetric reaction provides convenient and valuable access to highly functionalized 2-amino-4H-chromene derivatives, which possess important biological activities, in good yields with moderate to high enantioselectivities (up to 95% ee). (C) 2013 Elsevier Ltd. All rights reserved.
• C3-Symmetric cinchonine-squaramide as a recyclable efficient organocatalyst for tandem Michael addition–cyclisation of malononitrile and nitrovinylphenols
  作者：Wenxing Lv、Chao Guo、Ze Dong、Shi Tang、Bin Liu、Chune Dong

  DOI：10.1016/j.tetasy.2016.05.011

  日期：2016.8

  The tandem enantioselective Michael addition/cyclisation reaction of malononitrile and nitrovinylphenols was catalysed by a recoverable C-3-symmetric cinchonine-squaramide organocatalyst la to afford the 2-amino-4H-chromene-3-carbonitrile derivatives in excellent yields (up to 95%) and with excellent enantioselectivities (up to 98% ee) under mild reaction conditions. Furthermore, this catalyst can be easily recovered four times without loss in activity or enantioselectivity. (C) 2016 Elsevier Ltd. All rights reserved.