7-amino-9-phenyl-6-(trifluoromethyl)-6H-benzo[c]chromene-8-carbonitrile

• 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: 7-amino-9-phenyl-6-(trifluoromethyl)-6H-benzo[c]chromene-8-carbonitrile
• 化学式: C₂₁H₁₃F₃N₂O
• 分子量: 366.342
• InChiKey: YEXFVGCMITZCAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-nitro-2-(trifluoromethyl)-2H-chromene 、 2-(1-苯基亚乙基)丙二腈 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以41%的产率得到7-amino-9-phenyl-6-(trifluoromethyl)-6H-benzo[c]chromene-8-carbonitrile
  参考文献：
  名称：

  Domino reaction of 3-nitro-2-(trifluoromethyl)-2H-chromenes with 2-(1-phenylalkylidene)malononitriles: synthesis of functionalized 6-(trifluoromethyl)-6H-dibenzo[b,d]pyrans and a rare case of [1,5] sigmatropic shift of the nitro group

  摘要：

  A variety of functionalized 6-(trifluoromethyl)-6H-dibenzo[b,d]pyrans were easily synthesized in good yields under mild conditions by a domino reaction of 3-nitro-2-(trifluoromethyl)-2H-chromenes with 2-(1-phenylethylidene)- and 2-(1-phenylpropylidene)malononitriles. In the latter case, intermediate 7-amino-10-methyl-10-nitro-9-phenyl-6-(trifluoromethyl)-10,10a-dihydro-6H-benzo[c]chromene-8-carbonitriles were isolated as a result of a rare [1,5] sigmatropic shift of the nitro group. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.031

文献信息

• Domino reaction of 3-nitro-2-(trifluoromethyl)-2H-chromenes with 2-(1-phenylalkylidene)malononitriles: synthesis of functionalized 6-(trifluoromethyl)-6H-dibenzo[b,d]pyrans and a rare case of [1,5] sigmatropic shift of the nitro group
  作者：Vladislav Yu. Korotaev、Alexey Yu. Barkov、Vyacheslav Ya. Sosnovskikh

  DOI：10.1016/j.tet.2013.09.031

  日期：2013.11

  A variety of functionalized 6-(trifluoromethyl)-6H-dibenzo[b,d]pyrans were easily synthesized in good yields under mild conditions by a domino reaction of 3-nitro-2-(trifluoromethyl)-2H-chromenes with 2-(1-phenylethylidene)- and 2-(1-phenylpropylidene)malononitriles. In the latter case, intermediate 7-amino-10-methyl-10-nitro-9-phenyl-6-(trifluoromethyl)-10,10a-dihydro-6H-benzo[c]chromene-8-carbonitriles were isolated as a result of a rare [1,5] sigmatropic shift of the nitro group. (c) 2013 Elsevier Ltd. All rights reserved.