methyl 4-(2-firyl)-2-methyl-4-oxobutyrate | 162464-78-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 4-(2-firyl)-2-methyl-4-oxobutyrate
• 英文别名: methyl 4-(furan-2-yl)-2-methyl-4-oxobutanoate；Methyl 4-(furan-2-yl)-2-methyl-4-oxobutanoate
• CAS: 162464-78-0
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: LTDAXCWXAQPOBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(2-firyl)-2-methyl-4-oxobutyrate 在 lithium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 (R)-4-Furan-2-yl-2-methyl-4-oxo-N-((S)-1-phenyl-ethyl)-butyramide
  参考文献：
  名称：

  The Stereoselective Synthesis of 2-Alkyl .gamma.-Keto Acid and Heterocyclic Ketomethylene Peptide Isostere Core Units Using Chiral Alkylation by 2-Triflyloxy Esters

  摘要：

  A simple and general protocol for the enantioselective preparation of gamma-keto acids and heterocyclic gamma-keto acids which have an alkyl group at C-2 is reported. The alkyl group is introduced by chiral alkylation using a scalemic 2-triflyloxy ester. The alkylation takes place with inversion of configuration and is compatible with a variety of alkyl groups. This methodology is thus well-suited for the preparation of a wide variety of ketomethylene peptide isosteres.

  DOI：

  10.1021/jo00121a031
• 作为产物：
  描述：

  2-(Furan-2-carbonyl)-3-methyl-succinic acid 1-tert-butyl ester 4-methyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 methyl 4-(2-firyl)-2-methyl-4-oxobutyrate
  参考文献：
  名称：

  The Stereoselective Synthesis of 2-Alkyl .gamma.-Keto Acid and Heterocyclic Ketomethylene Peptide Isostere Core Units Using Chiral Alkylation by 2-Triflyloxy Esters

  摘要：

  A simple and general protocol for the enantioselective preparation of gamma-keto acids and heterocyclic gamma-keto acids which have an alkyl group at C-2 is reported. The alkyl group is introduced by chiral alkylation using a scalemic 2-triflyloxy ester. The alkylation takes place with inversion of configuration and is compatible with a variety of alkyl groups. This methodology is thus well-suited for the preparation of a wide variety of ketomethylene peptide isosteres.

  DOI：

  10.1021/jo00121a031

文献信息

• Oxidative Generation of<i>α</i>-Radicals of Carbonyl Compounds from the<i>α</i>-Stannyl Derivatives and Their Reactions with Electron-Rich Olefins
  作者：Yasushi Kohno、Koichi Narasaka

  DOI：10.1246/bcsj.68.322

  日期：1995.1

  of the alkanoates by eliminating the stannylium ion. The thus-formed radicals react with various electron-rich olefinic compounds, such as silyl enol ethers, giving addition products in good yield. This method formally achieves selective cross coupling between alkanoates and ketones.

  用四丁基六硝酸铵 (IV) 氧化 α-三丁基链烷酸甲烷基酯，通过消除锡鎓离子产生链烷酸酯的 α-自由基。由此形成的自由基与各​​种富含电子的烯烃化合物（例如甲硅烷基烯醇醚）反应，以良好的产率得到加成产物。该方法正式实现了链烷酸酯和酮之间的选择性交叉偶联。
• Decatungstate‐Catalyzed Carbon‐Carbon Bond Formation Between Furfural and Electron‐Deficient Olefins
  作者：Emil Krogh Nielsen、Kassem El‐Chami、Clara Mondrup de Lichtenberg、Robert Madsen

  DOI：10.1002/ejoc.202400109

  日期：2024.4.22

  Functionalization of furfural can be achieved by photocatalytic C−H activation of the aldehyde and coupling to electron-deficient olefins. With (Bu4N)4W10O32 as the photocatalyst, furfural can be added to benzylidene malononitriles, acrylates, itaconic anhydride, maleic anhydride, 2-vinylpyridine and phenyl vinyl sulfone to form the corresponding furanyl ketones in moderate-to-good yields.

  糠醛的官能化可以通过醛的光催化CH活化和与缺电子烯烃的偶联来实现。以(Bu 4 N) 4 W 10 O 32为光催化剂，糠醛可与亚苄基丙二腈、丙烯酸酯、衣康酸酐、马来酸酐、2-乙烯基吡啶、苯基乙烯基砜等反应生成相应的呋喃酮。产量。
• The Stereoselective Synthesis of 2-Alkyl .gamma.-Keto Acid and Heterocyclic Ketomethylene Peptide Isostere Core Units Using Chiral Alkylation by 2-Triflyloxy Esters
  作者：Robert V. Hoffman、Hwa-Ok Kim

  DOI：10.1021/jo00121a031

  日期：1995.8

  A simple and general protocol for the enantioselective preparation of gamma-keto acids and heterocyclic gamma-keto acids which have an alkyl group at C-2 is reported. The alkyl group is introduced by chiral alkylation using a scalemic 2-triflyloxy ester. The alkylation takes place with inversion of configuration and is compatible with a variety of alkyl groups. This methodology is thus well-suited for the preparation of a wide variety of ketomethylene peptide isosteres.