2-amino-7-[(2-bromophenyl)methoxy]-4-(3,4-dimethoxyphenyl)-4H-chromene-3-carbonitrile | 1427317-67-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 2-amino-7-[(2-bromophenyl)methoxy]-4-(3,4-dimethoxyphenyl)-4H-chromene-3-carbonitrile
• CAS: 1427317-67-6
• 化学式: C₂₅H₂₁BrN₂O₄
• 分子量: 493.357
• InChiKey: WMNQBWVHOFTKRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  86.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-7-[(2-bromophenyl)methoxy]-4-(3,4-dimethoxyphenyl)-4H-chromene-3-carbonitrile 在 palladium diacetate 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以58%的产率得到(3,4-dimethoxyphenyl)-(3-hydroxy-6H-benzo[c]chromen-2-yl)methanone
  参考文献：
  名称：

  Intramolecular Heck Reaction on Bromobenzyloxy-Substituted Chromenes: Formation of Chelated Ketones

  摘要：

  Heck reaction on 2-bromobenzyloxy-substituted 4H-chromene derivatives using Pd(OAc)(2) in Aliquat 336 and N,N-dimethylformamide mixture leads to intramolecular heteroannulation along with hydrolysis, affording chelated 6H-benzo[c]chromen-2-yl ketones. The method offers Pd(0)-catalysis and regioselectivity in product formation. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.655358
• 作为产物：
  描述：

  间苯二酚 在 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 生成 2-amino-7-[(2-bromophenyl)methoxy]-4-(3,4-dimethoxyphenyl)-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  Intramolecular Heck Reaction on Bromobenzyloxy-Substituted Chromenes: Formation of Chelated Ketones

  摘要：

  Heck reaction on 2-bromobenzyloxy-substituted 4H-chromene derivatives using Pd(OAc)(2) in Aliquat 336 and N,N-dimethylformamide mixture leads to intramolecular heteroannulation along with hydrolysis, affording chelated 6H-benzo[c]chromen-2-yl ketones. The method offers Pd(0)-catalysis and regioselectivity in product formation. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.655358

文献信息

• Intramolecular Heck Reaction on Bromobenzyloxy-Substituted Chromenes: Formation of Chelated Ketones
  作者：Amarendra Patra、Tanusri Mahapatra

  DOI：10.1080/00397911.2012.655358

  日期：2013.6.3

  Heck reaction on 2-bromobenzyloxy-substituted 4H-chromene derivatives using Pd(OAc)(2) in Aliquat 336 and N,N-dimethylformamide mixture leads to intramolecular heteroannulation along with hydrolysis, affording chelated 6H-benzo[c]chromen-2-yl ketones. The method offers Pd(0)-catalysis and regioselectivity in product formation. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.