(E)-6-chloro-3-(1,3-diphenylallyl)-4-hydroxy-2H-chromen-2-one | 1198104-39-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: (E)-6-chloro-3-(1,3-diphenylallyl)-4-hydroxy-2H-chromen-2-one
• 英文别名: 6-chloro-3-[(E)-1,3-diphenylprop-2-enyl]-4-hydroxychromen-2-one
• CAS: 1198104-39-0
• 化学式: C₂₄H₁₇ClO₃
• 分子量: 388.85
• InChiKey: OFFVKOKGRVVGDM-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-氯-4-羟基香豆素 、 1,3-diphenyl-3-hydroxypropene 在 碘 作用下， 以 硝基甲烷 为溶剂， 反应 1.0h， 以77%的产率得到(E)-6-chloro-3-(1,3-diphenylallyl)-4-hydroxy-2H-chromen-2-one
  参考文献：
  名称：

  Molecular iodine-catalyzed C3-alkylation of 4-hydroxycoumarins with secondary benzyl alcohols

  摘要：

  A highly efficient method for the C-C bond formation via molecular iodine-catalyzed C3-alkylation reaction of 4-hydroxycoumarins with benzylic, benzhydrylic, allylic, and propargyl alcohols at 50 degrees C in MeNO2 is described. The 3-alkylated-4-hydroxycoumarins were obtained in good yields (up to 97%). By applying this reaction as the key step, a multi-substituted pyranocoumarin can easily be synthesized in a one-pot procedure. The advantages of this method are broad scope, mild conditions, and easy handling since water is the only side product. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.007

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。