(S)-2-amino-6-methyl-4-nitromethyl-4H-chromene-3-carbonitrile | 1384291-04-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (S)-2-amino-6-methyl-4-nitromethyl-4H-chromene-3-carbonitrile
• 英文别名: (4S)-2-amino-6-methyl-4-(nitromethyl)-4H-chromene-3-carbonitrile
• CAS: 1384291-04-6
• 化学式: C₁₂H₁₁N₃O₃
• 分子量: 245.238
• InChiKey: JJSGZTZCFYHKJS-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (E)-4-methyl-2-(2-nitrovinyl)phenol 、 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92%的产率得到(S)-2-amino-6-methyl-4-nitromethyl-4H-chromene-3-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

• 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.
• Enantioselective organocatalytic synthesis of medicinally privileged 2-amino-4H-chromene-3-carbonitriles via a cascade process
  作者：Zhiyun Du、Woon-Yew Siau、Jian Wang

  DOI：10.1016/j.tetlet.2011.09.030

  日期：2011.11

  An efficient organocatalytic cascade approach toward medicinally privileged 2-amino-4H-chromene-3-carbonitriles is reported. The enantioselective synthesis of these compounds is achieved in high yields and good to high ee values (up to 96% yield and 89% ee) using bifunctional amine-thiourea organocatalysts developed in our laboratory. (C) 2011 Elsevier Ltd. All rights reserved.