2-(2,5-dimethoxyphenyl)-3-hydroxynaphthalene-1,4-dione | 1240385-26-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2,5-dimethoxyphenyl)-3-hydroxynaphthalene-1,4-dione
• CAS: 1240385-26-5
• 化学式: C₁₈H₁₄O₅
• 分子量: 310.306
• InChiKey: OYNUPFCIAWZBGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2,5-二甲氧基苯甲醛 、 碘正离子,苯基-,3,4-二氢-1,3,4-三羰基-2(1H)-萘自由基负离子 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以99%的产率得到2-(2,5-dimethoxyphenyl)-3-hydroxynaphthalene-1,4-dione
  参考文献：
  名称：

  Arylation of lawsone through BF3-mediated coupling of its phenyliodonium ylide with activated arenes and aromatic aldehydes

  摘要：

  Phenyliodonium ylide of lawsone, activated by BF3 center dot Et2O, reacts with electron-rich arenes to afford the corresponding 2-aryl-3-hydroxy-1,4-naphthoquinones, in a coupling reaction without metal catalysts. The same type of products, in greater variety and higher yields, are obtained from the reaction of the BF3 center dot Et2O-activated ylide with aromatic aldehydes in a synthetically and mechanistically interesting deformylation reaction. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.120

文献信息

• Styryl and functionalized aryl derivatives of lawsone through metal-free cross-coupling of its BF3-activated phenyliodonium ylide with cinnamaldehydes and arylaldehydes
  作者：Elizabeth Malamidou-Xenikaki、Maria Tsanakopoulou、Maria Chatzistefanou、Dimitra Hadjipavlou-Litina

  DOI：10.1016/j.tet.2015.06.037

  日期：2015.8

  Phenyliodonium ylide of lawsone activated with BF3 center dot Et2O reacts with cinnamaldehydes to afford 2-hydroxy-3-styryl-1,4-naphthoquinones in good to excellent yields and relatively high level of stereospecificity through deformylation of the aldehydes. The product yield is diminished with a methoxy substituted cinnamaldehyde and becomes zero with a dimethoxy substituted substrate giving rise to another product, 2-hydroxy-3-aryl-1,4-naphthoquinone. The reaction of the same ylide with salicylic aldehydes forms 2-hydroxy-3-(2-hydroxyary1)-1,4-naphthoquinones and/or benzo[d]naphtha[2,1-b]furano-5,6-diones, depending on the reaction conditions applied. Plausible reaction mechanisms explaining the formation of these products are proposed. The products showed potent antioxidant activity and inhibited lipoxygenase. (C) 2015 Elsevier Ltd. All rights reserved.