2,4-diphenylpyrano[3,2-c]chromen-5(2H)-one | 10173-98-5

• 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-diphenylpyrano[3,2-c]chromen-5(2H)-one
• 英文别名: 2,4-diphenyl-2H,5H-pyrano[3,2-c]chromen-5-one；2,4-diphenyl-2H-pyrano[3,2-c]chromen-5-one；3,4-<2',4'-Diphenyl-1',2'-pyrano>-cumarin
• CAS: 10173-98-5
• 化学式: C₂₄H₁₆O₃
• 分子量: 352.389
• InChiKey: GHEBXDBEUNZJIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.36
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  39.44
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (E)-3-(1,3-diphenylallyl)-4-hydroxy-2H-chromen-2-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 反应 1.0h， 以282 mg的产率得到2,4-diphenylpyrano[3,2-c]chromen-5(2H)-one
  参考文献：
  名称：

  HFIP Promoted C3 Alkylation of Lawsone and 4-Hydroxycoumarin with Alcohols by Dehydrative Cross-Coupling

  摘要：

  An environmentally benign system for the direct alkylation of lawsones and 4-hydroxycoumarins with alcohols in 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) is reported. The reaction proceeded smoothly via a dehydrative cross-coupling process by utilizing the unique properties of HFIP. A variety of alkylated products and subsequent one-pot cyclized products (pyranonaphthoquinones and pyranocoumarins) could be obtained in 40-93% yields.

  DOI：

  10.1021/acs.joc.0c01207

文献信息

• CDC Reaction and Subsequent Cyclization for the Synthesis of 2-Hydroxy-3-alkyl-1,4-naphthoquinones and Pyranonaphthoquinones
  作者：Dongping Cheng、Lijun Wu、Huawei Lv、Xiaoliang Xu、Jizhong Yan

  DOI：10.1021/acs.joc.6b02787

  日期：2017.2.3

  coupling (CDC) reaction and subsequent cyclization of 2-hydroxy-1,4-naphthoquinone (lawsone) and 1,3-diarylpropene promoted by DDQ has been developed. 2-Hydroxy-3-alkyl-1,4-naphthoquinones and pyranonaphthoquinones with potential pharmaceutical applications are obtained in moderate to good yields. The reaction is also compatible for 4-hydroxycoumarins.

  已经开发了无金属的交叉脱氢偶联（CDC）反应以及随后由DDQ促进的2-羟基-1,4-萘醌（草酮）和1,3-二芳基丙烯的环化反应。以中等至良好的产率获得了具有潜在药物应用的2-羟基-3-烷基-1,4-萘醌和吡喃并萘醌。该反应也与4-羟基香豆素相容。