2,4-bis(4-bromophenyl)pyrano[3,2-c]chromen-5(4H)-one | 1204525-23-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 2,4-bis(4-bromophenyl)pyrano[3,2-c]chromen-5(4H)-one
• 英文别名: 2,4-bis(4-bromophenyl)-4H-pyrano[3,2-c]chromen-5-one
• CAS: 1204525-23-4
• 化学式: C₂₄H₁₄Br₂O₃
• 分子量: 510.181
• InChiKey: UAPDSOCOSQJESH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 、 1,3-bis(4-bromophenyl)-2-propen-1-one 在 tin(II) trifluoromethanesulfonate 、 tert-butylammonium hexafluorophosphate(V) 作用下， 以 neat (no solvent) 为溶剂， 反应 3.0h， 以70%的产率得到2,4-bis(4-bromophenyl)pyrano[3,2-c]chromen-5(4H)-one
  参考文献：
  名称：

  Alkaline earth metal catalyzed cascade, one-pot, solvent-free, and scalable synthesis of pyranocoumarins and benzo[b]pyrans

  摘要：

  Ca(OTf)(2) catalyzed, cascade, one-pot, conjugate addition and annulation of various nucleophiles to the alpha,beta-unsaturated carbonyl compounds for the synthesis of biologically potent pyranocoumarins and benzo[b]pyrans has been illustrated. This one-pot, solvent-free, green-synthesis employs simple reaction conditions, with high yields and endures the substrate diversity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.02.023

文献信息

• DDQ-Mediated Tandem Synthesis of Functionalized Pyranocoumarins from 4-Hydroxycoumarins and 1,3-Diarylallylic Compounds
  作者：Xufeng Lin、Zhenxing He、Yuanxun Zhu、Yanguang Wang

  DOI：10.3987/com-10-11906

  日期：——

  simple and efficient DDQ-mediated oxidative cross-coupling between 4-hydroxycoumarin and 1,3-diarylallylic compounds was developed. The reaction furnished functionalized pyranocoumarins in a single step without using any metal catalyst. The tandem process involves an intermolecular C-C bond formation and an intramolecular C-O bond formation through double oxidative C-H activation.

  开发了一种简单有效的 DDQ 介导的 4-羟基香豆素和 1,3-二芳基烯丙基化合物之间的氧化交叉偶联。该反应在一个步骤中提供了官能化的吡喃香豆素，而不使用任何金属催化剂。串联过程涉及通过双氧化 CH 活化形成分子间 CC 键和形成分子内 CO 键。
• Alkaline earth metal catalyzed cascade, one-pot, solvent-free, and scalable synthesis of pyranocoumarins and benzo[b]pyrans
  作者：Srinivasarao Yaragorla、Pyare Lal Saini、Garima Singh

  DOI：10.1016/j.tetlet.2015.02.023

  日期：2015.3

  Ca(OTf)(2) catalyzed, cascade, one-pot, conjugate addition and annulation of various nucleophiles to the alpha,beta-unsaturated carbonyl compounds for the synthesis of biologically potent pyranocoumarins and benzo[b]pyrans has been illustrated. This one-pot, solvent-free, green-synthesis employs simple reaction conditions, with high yields and endures the substrate diversity. (C) 2015 Elsevier Ltd. All rights reserved.