2-(4-methoxyphenyl)-6-nitro-2H-chromene | 1133728-85-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(4-methoxyphenyl)-6-nitro-2H-chromene
• CAS: 1133728-85-4
• 化学式: C₁₆H₁₃NO₄
• 分子量: 283.284
• InChiKey: BEIIYYZKHGDMTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  61.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-6-nitro-2H-chromene 在 iron(III) chloride hexahydrate 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 (E)-5a-(4-methoxyphenyl)-11-(4-methoxystyryl)-2,9-dinitro-5a,11,11a,12-tetrahydrochromeno[2,3-b]chromene 、 (E)-5a-(4-methoxyphenyl)-11-(4-methoxystyryl)-2,9-dinitro-5a,11,11a,12-tetrahydrochromeno[2,3-b]chromene
  参考文献：
  名称：

  Iron-Catalyzed Rearrangements and Cycloaddition Reactions of 2H-Chromenes

  摘要：

  Iron(III) salts catalyze the tandem rearrangement/hetero-Diels-Alder reaction of 2H-chromenes to yield tetrahydrochromeno heterocycles. The process can occur as a homodimerization and cycloaddition process using electron-rich dienophiles. Deuterium labeling and mechanistic studies revealed a hydride shift and ortho-quinone methide cycloaddition reaction pathway.

  DOI：

  10.1021/ol202772k
• 作为产物：
  描述：

  6-nitro-4H-chromene 、 4-methoxybenzenediazonium tetrafluoroborate 在 2,6-二叔丁基-4-甲基吡啶 、 palladium diacetate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 2.5h， 以53%的产率得到2-(4-methoxyphenyl)-6-nitro-2H-chromene
  参考文献：
  名称：

  The scope of the Heck arylation of enol ethers with arenediazonium salts: a new approach to the synthesis of flavonoids

  摘要：

  The scope of the Heck arylation of cyclic and acyclic enol ethers with arenediazonium salts was evaluated. Arylation of 2,3-dihydrofuran yielded 2-aryl-2,5-dihydrofurans as the major adducts (>99:1) except when using n-Bu4NHSO4 as additive or 4-NO2PhN2BF4 as arenediazonium salt. 2,3-Dihydropyran provided mixtures of the three possible isomeric Heck adducts. Arylation of n-butylvinylether with arenediazonium bearing electron-donating groups resulted in substituted acetophenones as almost exclusive products in good overall yields, Substituted 4H-chromenes provided 2-aryl-2H-chromenes in moderate yield when applying the Pd(OAc)(2)/2,6-di-t-butyl-4-methylpyridine catalytic system, which were applied in the synthesis of flavonoids. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.017