ethyl 3-(4-methoxyphenyl)-2,2-dimethyl-3-oxopropanoate | 874487-04-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3-(4-methoxyphenyl)-2,2-dimethyl-3-oxopropanoate
• 英文别名: Ethyl 2,2-dimethyl-3-oxo-3-(4-methoxyphenyl)propionate
• CAS: 874487-04-4
• 化学式: C₁₄H₁₈O₄
• mdl: MFCD16326829
• 分子量: 250.295
• InChiKey: JAXGZXZKVGXUIK-UHFFFAOYSA-N

物化性质

• 沸点：
  347.6±17.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 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：

  ethyl 3-(4-methoxyphenyl)-2,2-dimethyl-3-oxopropanoate 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 72.0h， 以73%的产率得到3-(4-methoxyphenyl)-4,4-dimethyl-isoxazol-5(4H)-one
  参考文献：
  名称：

  异戊醛-5（4H）-1与醛的钯催化氮杂-维蒂希型缩合

  摘要：

  本文描述了在PPh 3存在下异恶唑5（4 H）-one与羰基化合物的钯催化脱羧分子间和分子内缩合反应的发展 ，给出了各种2-azabuta-1,3-二烯或吡咯中等至高产。

  DOI：

  10.1002/chem.201304211
• 作为产物：
  描述：

  对甲氧基苯甲酰氯 、 异丁酸乙酯 在 三苯甲基钠 作用下， 生成 ethyl 3-(4-methoxyphenyl)-2,2-dimethyl-3-oxopropanoate
  参考文献：
  名称：

  AROYLATIONS OF ETHYL ISOBUTYRATE BY ALKALI TRIPHENYL-METHIDES. ISOLATION OF β-KETO ESTERS BY CHROMATOGRAPHY. USE OF A REAGENT HAVING AN AMINO GROUP^{1, 2}

  摘要：

  DOI：

  10.1021/jo01374a013

文献信息

• Facile synthesis of δ-ketoesters via formal two-carbon insertion into β-ketoesters
  作者：Yan Jiang、Song Xi、Qi Wang、Lin Fu、Ling He、Zhen Wang、Min Zhang

  DOI：10.1016/j.tetlet.2022.153656

  日期：2022.3

  A formal two-carbon insertion into β-ketoesters with vinylmetal has been developed for the rapid synthesis of δ-ketoesters. This method features high efficiency, simple operation, and mild conditions without the usage of bases and catalysts. The reaction is postulated to proceed via a tandem process involving nucleophilic addition of vinylmetal to ketone, retro-aldol reaction to give an enolate anion

  已经开发了一种正式的用乙烯基金属将双碳插入到β-酮酯中的方法，用于快速合成δ-酮酯。该方法具有效率高、操作简单、条件温和等特点，无需使用碱和催化剂。假设该反应通过串联过程进行，包括乙烯基金属与酮的亲核加成、逆醛醇反应产生烯醇化物阴离子和烯酮，最后是这两种中间体的迈克尔加成。
• A Reformatsky Type Condensation of Aroyl Chlorides with Ethyl α-Bromoisobutyrate by Means of Zinc to Form β-Keto Esters^1,2
  作者：P. L. Bayless、Charles R. Hauser

  DOI：10.1021/ja01638a007

  日期：1954.5
• Lapin,H.; Horeau,A., Gazzetta Chimica Italiana, 1963, vol. 93, p. 451 - 454
  作者：Lapin,H.、Horeau,A.

  DOI：——

  日期：——
• Radical N-heterocyclic carbene catalysis for β-ketocarbonyl synthesis
  作者：Takuya Ishii、Kazunori Nagao、Hirohisa Ohmiya

  DOI：10.1016/j.tet.2021.132212

  日期：2021.7
• Synthesis and Structure-Activity Relationships of Miticidal 4,5-Dihydropyrazole-5-thiones
  作者：Isao Tada、Minoru Motoki、Nobuyoshi Takahashi、Tetsuji Miyata、Tomoko Takechi、Toshiro Uchida、Yasushi Takagi

  DOI：10.1002/(sici)1096-9063(199610)48:2<165::aid-ps455>3.0.co;2-z

  日期：1996.10

  A series of novel 4,5-dihydropyrazole-5-thiones (DHPs) was synthesised by treating the corresponding dihydropyrazolones with Lawesson's reagent and evaluated for miticidal activity against two-spotted spider mites (Tetranychus urticae Koch). Of these, 3-(4-chlorophenyl)-4,4-dimethyl-1-phenyl-4, 5-dihydropyrazole-5-thione, 3-(4-chlorophenyl)-4-ethyl-4-methyl-1-phenyl-4,5-dihydropyrazole-5-thione, 3-(4-chlorophenyl)-1-phenyl-4,5-dihydropyrazole-5-thione-4-spirocyclopentane and 4,4-dimethyl-1-phenyl-3-(4-trifluoromethyl-phenyl)-4,5-dihydropyrazole-5-thione were highly active (pEC(50) > 4 . 0) and were more effective than the miticide dicofol (pEC(50) = 3 . 879), which has traditionally been used for the control of phytophagous mites. Structure-activity relationship (SAR) studies were performed on each position of the pyrazole ring of DHPs. The results indicated that the unsubstituted phenyl, 4-substituted phenyl and thioxo groups on the 1-, 3- and 5-positions of DHPs respectively were required for activity. Quantitative SAR studies using physicochemical parameters of substituents and the capacity factor k' as a hydrophobicity index suggested that: (a) the activities of all types of DHPs examined were mainly dominated by hydrophobicity, (b) the bulkiness of 4-substituents of the 3-phenyl ring favoured the activity and (c) the log k' optimum for all DHPs was 1 . 675, equivalent to a log P-ow value of c. 5 . 0.