2-Methyl-4-(2-furyl)-4-oxobutanoic acid | 63319-73-3

• 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: 2-Methyl-4-(2-furyl)-4-oxobutanoic acid
• 英文别名: 4-(2-furyl)-2-methyl-4-oxobutanoic acid；4-(2-Furyl)-2-methyl-4-oxobuttersaeure；4-furan-2-yl-2-methyl-4-oxo-butyric acid；4-(Furan-2-yl)-2-methyl-4-oxobutanoic acid
• CAS: 63319-73-3
• 化学式: C₉H₁₀O₄
• 分子量: 182.176
• InChiKey: KYFCSFXACFKXQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Methyl-4-(2-furyl)-4-oxobutanoic acid 、 (S)-(-)- α-甲基苄胺 在 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， 生成 (S)-4-Furan-2-yl-2-methyl-4-oxo-N-((S)-1-phenyl-ethyl)-butyramide 、 (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：

  methyl 4-(2-firyl)-2-methyl-4-oxobutyrate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 2-Methyl-4-(2-furyl)-4-oxobutanoic acid
  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

• Magnesium-Promoted Reductive Carboxylation of Aryl Vinyl Ketones: Synthesis of γ-Keto Carboxylic Acids
  作者：Suhua Zheng、Tianyuan Zhang、Hirofumi Maekawa

  DOI：10.1021/acs.joc.2c00557

  日期：2022.6.3

  Direct reductive carboxylation of easily prepared aryl vinyl ketones under the atmosphere of carbon dioxide led to the selective formation of γ-keto carboxylic acids in 38–86% yields. The reaction is characterized by the carbon–carbon bond formation of carbon dioxide at the β-position of enone, with the use of magnesium turnings that can be easily handled as the reducing agent and the eco-friendly

  容易制备的芳基乙烯基酮在二氧化碳气氛下的直接还原羧化导致以 38-86% 的产率选择性形成 γ-酮基羧酸。该反应的特点是二氧化碳在烯酮的β位形成碳-碳键，使用易于处理的镁屑作为还原剂，以及无加压、无压力等环保反应条件。反应温度低或高，反应时间短。该协议显示了广泛的底物范围，并提供了一种有用且方便的替代方法来获取生物学上重要的 γ-酮羧酸。
• STETTER H.; KUHLMANN H., TETRAHEDRON <TETR-AB>, 1977, 33, NO 3, 353-356
  作者：STETTER H.、 KUHLMANN H.

  DOI：——

  日期：——
• 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.