1-(2,4-dimethoxyphenyl)-3-phenyl-1,3-propanedione | 80370-26-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(2,4-dimethoxyphenyl)-3-phenyl-1,3-propanedione
• 英文别名: 1-(2,4-dimethoxyphenyl)-3-phenylpropane-1,3-dione；1-(2,4-Dimethoxy-phenyl)-3-phenyl-propan-1,3-dion
• CAS: 80370-26-9
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: AEEAKBXAXKZQPA-UHFFFAOYSA-N

物化性质

• 熔点：
  37-40 °C
• 沸点：
  463.7±35.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2,4-dimethoxyphenyl)-3-phenyl-1,3-propanedione 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以84%的产率得到7-甲氧基黄酮
  参考文献：
  名称：

  K₂CO₃-Catalyzed Synthesis of Chromones and 4-Quinolones through the Cleavage of Aromatic C–O Bonds

  摘要：

  Phenol-derived electrophiles are favorable substrates because phenols are naturally abundant or can be readily prepared from other aromatic compounds. However, the cleavage of aromatic C-O bonds Is a great challenge because of their high energy. K2CO3-catalyzed intramolecular cyclization of 1-(2-alkoxyphenyl)-3-akylpropane-1,3-dlone and 3-(alkylimino)-1-(2-methoxyphenyl)-2-methylpropan-1-one derivatives via the selective cleavage of aromatic C-O bonds Is reported. The corresponding chromone and 4-quinolone derivatives were obtained in reasonable yields.

  DOI：

  10.1021/ol300908g
• 作为产物：
  描述：

  2,4-二甲氧基苯甲酸 在 乙醚 、 硫酸 、 sodium 作用下， 生成 1-(2,4-dimethoxyphenyl)-3-phenyl-1,3-propanedione
  参考文献：
  名称：

  Perkin; Schiess, Journal of the Chemical Society, 1904, vol. 85, p. 162

  摘要：

  DOI：

文献信息

• Synthesis of Dibenzoylmethane Derivaives and Inhibition of Mutagenicity in Salmonella typhimurium.
  作者：Tominari CHOSHI、Shigenori HORIMOTO、Ching Y. WANG、Hisamitsu NAGASE、Masataka ICHIKAWA、Eiichi SUGINO、Satoshi HIBINO

  DOI：10.1248/cpb.40.1047

  日期：——

  Twenty dibenzoylmethanes with methyl, methoxy, bromo, chloro, or fluoro substitution on either one or both benzene rings were synthesized and assayed for inhibition of the mutagenicity of 2-nitrofluorene in S. typhimurium TA98. 2, 2-Dimethoxy, 3, 3-dimethoxy and 3, 3, 4, 4-tetramethoxydibenzoylmethane was as active as dibenzoylmethane. None of the halogen-substituted dibenzoylmethanes were active. These results demonstrate that dibenzoylmethanes can inhibit the mutagenicity of 2-nitrofluorene, and that modifications made on the benzene rings of dibenzoylmethane cannot enhance the antimutagencity of this parent compound.

  合成了20种二苯甲酰甲烷，它们在一个或两个苯环上分别带有甲基、甲氧基、溴、氯或氟取代基，并测定了它们对S. typhimurium TA98株2-硝基芴致突变性的抑制作用。2,2-二甲氧基、3,3-二甲氧基和3,3,4,4-四甲氧基二苯甲酰甲烷与二苯甲酰甲烷同样有效。所有含卤素取代的二苯甲酰甲烷均无效。这些结果表明二苯甲酰甲烷能抑制2-硝基芴的致突变性，在二苯甲酰甲烷的苯环上作修饰并不能增强其母体化合物的抗致突变性。
• Significant Enhancement in the Efficiency and Selectivity of Iron-Catalyzed Oxidative Cross-Coupling of Phenols by Fluoroalcohols
  作者：Eden Gaster、Yulia Vainer、Almog Regev、Sachin Narute、Kavitha Sudheendran、Aviya Werbeloff、Hadas Shalit、Doron Pappo

  DOI：10.1002/anie.201409694

  日期：2015.3.27

  Significant enhancement of both the rate and the chemoselectivity of iron‐catalyzed oxidative coupling of phenols can be achieved in fluorinated solvents, such as 1,1,1,3,3,3‐hexafluoropropan‐2‐ol (HFIP), 2,2,2‐trifluoroethanol (TFE), and 1‐phenyl‐2,2,2‐trifluoroethanol. The generality of this effect was examined for the cross‐coupling of phenols with arenes and polycyclic aromatic hydrocarbons (PAHs)

  在氟化溶剂（例如1,1,1,3,3,3-六氟丙烷-2-醇（HFIP），2,2）中，可以显着提高苯酚的铁催化氧化偶联的速率和化学选择性。 ，2-三氟乙醇（TFE）和1-苯基-2-2,2,2-三氟乙醇。考察了苯酚与芳烃和多环芳烃（PAHs）以及苯酚与β-二羰基化合物的交叉偶联的普遍性。新的条件仅在四个合成步骤中就用于合成2'''-dehydroxycalodeninB。
• Metal‐Free, DBU‐Mediated, Microwave‐Assisted Synthesis of Benzo[ <i>c</i> ]xanthones by Tandem Reactions of Alkynyl‐1,3‐diketones
  作者：Yi‐En Liang、Balaji D. Barve、Yao‐Haur Kuo、Hsu‐Wei Fang、Ting‐Shen Kuo、Wen‐Tai Li

  DOI：10.1002/adsc.202001169

  日期：2021.1.19

  base‐mediated, green, microwave‐assisted efficient preparation of a diverse benzoxanthone library from variety of readily accessible γ‐alkynyl 1,3‐diketones is reported. The synthesis is based on tandem reactions involving intramolecular cyclization, propargyl‐allenyl isomerization, and electrocyclization in one pot. Some of the benzoxanthones are also synthesized by the one‐pot reaction of 1,3‐diketone and

  据报道，可以通过碱介导的，绿色的，微波辅助的方法，从各种容易获得的γ-炔基1,3-二酮中高效​​制备各种苯并蒽酮文库。该合成基于串联反应，涉及一分子内的分子内环化，炔丙基-烯丙基异构化和电环化。在碱性加热条件下，1,3-二酮与炔基溴的一锅反应也合成了一些苯并氧杂蒽。这种转变还导致一个新的C-C键和一个新的C-O键的构建。
• Robinson; Turner, Journal of the Chemical Society, 1918, vol. 113, p. 876
  作者：Robinson、Turner

  DOI：——

  日期：——
• Bradley; Robinson, Journal of the Chemical Society, 1926, p. 2363
  作者：Bradley、Robinson

  DOI：——

  日期：——