(S)-2-amino-6,8-dibromo-4-(nitromethyl)-4H-chromene-3-carbonitrile | 1384291-01-3

• 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-6,8-dibromo-4-(nitromethyl)-4H-chromene-3-carbonitrile
• 英文别名: (S)-2-amino-6,8-dibromo-4-nitromethyl-4H-chromene-3-carbonitrile；(4S)-2-amino-6,8-dibromo-4-(nitromethyl)-4H-chromene-3-carbonitrile
• CAS: 1384291-01-3
• 化学式: C₁₁H₇Br₂N₃O₃
• 分子量: 389.003
• InChiKey: CVQVQCFTRYMYMU-QMMMGPOBSA-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：

  (E)-2,4-dibromo-6-(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 2.0h， 以76%的产率得到
  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

• 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。