(S)-2-amino-4-nitromethyl-4H-chromene-3-carbonitrile | 1374979-98-2

• 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-4-nitromethyl-4H-chromene-3-carbonitrile
• 英文别名: 2-amino-4-(nitromethyl)-4H-chromene-3-carbonitrile；(4S)-2-amino-4-(nitromethyl)-4H-chromene-3-carbonitrile
• CAS: 1374979-98-2
• 化学式: C₁₁H₉N₃O₃
• 分子量: 231.211
• InChiKey: GVHATMLORGLBJM-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  反-2-羟基-β-硝基苯乙烯 、 丙二腈 在 CSCS 作用下， 以 二氯甲烷 为溶剂， 反应 24.17h， 以95%的产率得到(S)-2-amino-4-nitromethyl-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  C3-Symmetric cinchonine-squaramide as a recyclable efficient organocatalyst for tandem Michael addition–cyclisation of malononitrile and nitrovinylphenols

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2016.05.011

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
• Efficient organocatalytic asymmetric synthesis of 2-amino-4H-chromene-3-carbonitrile derivatives
  作者：Yu Gao、Wen Yang、Da-Ming Du

  DOI：10.1016/j.tetasy.2012.02.019

  日期：2012.3

  enantioselective tandem Michael addition–cyclization of malononitrile to nitroalkenes for the direct synthesis of chiral 2-amino-4H-chromene-3-carbonitrile derivatives was investigated. Good yields and enantioselectivities (up to 91% ee) were achieved. This organocatalytic asymmetric tandem Michael addition–cyclization provides an efficient route toward the synthesis of optically active functionalized chromenes

  的有机催化对映选择性串联迈克尔丙二腈的加成环化硝基烯烃为手性2-氨基-4-直接合成ħ色烯-3-甲腈衍生物进行了研究。获得了良好的收率和对映选择性（高达91％ee）。这种有机催化不对称串联的迈克尔加成环化为合成光学活性官能化二苯甲基提供了一条有效途径。
• Highly efficient enantioselective three-component synthesis of 2-amino-4H-chromenes catalysed by chiral tertiary amine-thioureas
  作者：Gaosheng Yang、Chongrong Luo、Xiaolong Mu、Tingting Wang、Xin-Yuan Liu

  DOI：10.1039/c2cc30731f

  日期：——

  A three-component cascade reaction of salicylaldehyde, malononitrile/cyanoacetate and nitromethane catalysed by chiral tertiary amino-thioureas was developed, which leads to the production of highly functionalized 2-amino-4H-chromenes in good yields with good to excellent enantioselectivities.

  在手性叔胺硫脲的催化下，开发了水杨醛、丙二腈/氰基乙酸酯和硝基甲烷的三组分级联反应，从而以良好的产率和良好至卓越的对映选择性制备出高度官能化的 2-氨基-4H-苯并吡喃。
• 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.