(R)-2-amino-6,8-dibromo-4-(nitromethyl)-4H-chromene-3-carbonitrile | 1374979-97-1

• 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: (R)-2-amino-6,8-dibromo-4-(nitromethyl)-4H-chromene-3-carbonitrile
• 英文别名: (R)-2-amino-6,8-dibromo-4-nitromethyl-4H-chromene-3-carbonitrile；(4R)-2-amino-6,8-dibromo-4-(nitromethyl)-4H-chromene-3-carbonitrile
• CAS: 1374979-97-1
• 化学式: C₁₁H₇Br₂N₃O₃
• 分子量: 389.003
• InChiKey: CVQVQCFTRYMYMU-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 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：

  、 丙二腈 在 3-[[[3,5-双（三氟甲基）苯基]氨基]-4-[[（（1R，2R）-1,2-二苯基-2-（1-哌啶基）乙基]氨基]-3-环丁烯-1，2-二酮 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以85%的产率得到(R)-2-amino-6,8-dibromo-4-(nitromethyl)-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  Chiral bifunctional squaramide catalyzed asymmetric tandem Michael-cyclization reaction: efficient synthesis of optically active 2-amino-4H-chromene-3-carbonitrile derivatives

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2013.07.010

文献信息

• 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。
• Novel thiophosphonodiamides as efficient hydrogen bond donor catalysts in tandem Michael addition–cyclization of malononitrile and 2-(E)-2-nitrovinylphenols
  作者：Keling Hu、Youming Wang、Zhenghong Zhou、Chuchi Tang

  DOI：10.1016/j.tet.2013.11.099

  日期：2014.1

  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.
• 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.