2,2-Dimethyl-3-oxo-3-o-tolyl-propionic acid methyl ester | 193828-16-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-Dimethyl-3-oxo-3-o-tolyl-propionic acid methyl ester
• 英文别名: Methyl 2,2-dimethyl-3-(2-methylphenyl)-3-oxopropanoate
• CAS: 193828-16-9
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: XVQHXBPINCKACS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-3-oxo-3-o-tolyl-propionic acid methyl ester 以 正己烷 为溶剂， 反应 96.0h， 生成 2-(7-Hydroxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-yl)-2-methyl-propionic acid methyl ester
  参考文献：
  名称：

  Solvent Dependent Photochemical Reactions of 3-(2-Alkylphenyl)-2,2-dimethyl-3-oxopropanoates and Their Related Compounds

  摘要：

  Photochemical reactions of methyl 3-(o-alkylphenyl)-2,2-dimethyl-3-oxopropanotes in hexane gave only the corresponding benzocyclobutenols. However, when irradiation was carried out in methanol, 3-oxonaphthalenones were produced together with the benzocyclobutenols. The ratio of benzocyclobutenol to naphthalenone depends on the bulkiness of the alkyl group in the ortho position. Intermediary 1,4-diradicals or dienols were efficiently trapped by oxygen to afford the corresponding peroxides and/or oxygenated compounds derived from the peroxides.

  DOI：

  10.1021/jo981433b
• 作为产物：
  描述：

  3-氧代-3-(2-甲苯基)丙酸甲酯 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 2,2-Dimethyl-3-oxo-3-o-tolyl-propionic acid methyl ester
  参考文献：
  名称：

  苯酚和环肟铜催化合成苯并恶唑

  摘要：

  报道了一种由游离酚和环肟酯催化直接合成苯并恶唑的方法。温和的反应条件耐受两种底物上的各种吸电子和给电子官能团，以中等至良好的产率提供苯并恶唑。使用该协议，证明了在一个或两个步骤中大规模合成Ezutromid和Flunoxaprofe 。提出了一种催化机制，包括通过内球电子转移和随后的环化进行铜催化胺化。

  DOI：

  10.1021/acs.orglett.1c04322

文献信息

• A Synthesis of α,α-Disubstituted Aryl-β-ketoesters
  作者：Mark Stefaniak、Fabrice Tinardon、John Wallis

  DOI：10.1055/s-1997-3249

  日期：1997.6

  applicable synthesis of alpha,alpha-disubstituted beta-ketoesters involving reaction of a substituted benzoyl chloride with methyl trimethylsilyl ketene acetal is described. Addition of boron trifluoride etherate is essential when the benzoyl chloride is nor substituted with a strongly electron withdrawing residue. The majority of experiments were conducted with the dimethylketene acetal but the process

  描述了一种普遍适用的 α，α-二取代 β-酮酯合成，包括取代苯甲酰氯与甲基三甲基甲硅烷基乙烯酮缩醛的反应。当苯甲酰氯未被强吸电子残基取代时，添加三氟化硼醚合物是必不可少的。大多数实验是用二甲基乙烯酮缩醛进行的，但该过程同样适用于环己烷乙烯酮缩醛 5。
• Solvent Dependent Photochemical Reactions of 3-(2-Alkylphenyl)-2,2-dimethyl-3-oxopropanoates and Their Related Compounds
  作者：Masaichi Saito、Yumiko Kamei、Kanae Kuribara、Michikazu Yoshioka、Tadashi Hasegawa

  DOI：10.1021/jo981433b

  日期：1998.11.1

  Photochemical reactions of methyl 3-(o-alkylphenyl)-2,2-dimethyl-3-oxopropanotes in hexane gave only the corresponding benzocyclobutenols. However, when irradiation was carried out in methanol, 3-oxonaphthalenones were produced together with the benzocyclobutenols. The ratio of benzocyclobutenol to naphthalenone depends on the bulkiness of the alkyl group in the ortho position. Intermediary 1,4-diradicals or dienols were efficiently trapped by oxygen to afford the corresponding peroxides and/or oxygenated compounds derived from the peroxides.
• Cu-Catalyzed Synthesis of Benzoxazole with Phenol and Cyclic Oxime
  作者：Zheng-Hai Wang、Dong-Hui Wang

  DOI：10.1021/acs.orglett.1c04322

  日期：2022.1.21

  A Cu-catalyzed straightforward synthesis of benzoxazoles from free phenols and cyclic oxime esters is reported. The mild reaction conditions tolerate various electron-withdrawing and electron-donating functional groups on both substrates, affording benzoxazoles in moderate to good yields. With this protocol, large-scale syntheses of Ezutromid and Flunoxaprofe in one or two steps are demonstrated. A

  报道了一种由游离酚和环肟酯催化直接合成苯并恶唑的方法。温和的反应条件耐受两种底物上的各种吸电子和给电子官能团，以中等至良好的产率提供苯并恶唑。使用该协议，证明了在一个或两个步骤中大规模合成Ezutromid和Flunoxaprofe 。提出了一种催化机制，包括通过内球电子转移和随后的环化进行铜催化胺化。