2-Methyl-3-(pyridine-2-carbonyl)-succinic acid 4-tert-butyl ester 1-methyl ester | 170115-33-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Methyl-3-(pyridine-2-carbonyl)-succinic acid 4-tert-butyl ester 1-methyl ester
• 英文别名: 4-O-tert-butyl 1-O-methyl 2-methyl-3-(pyridine-2-carbonyl)butanedioate
• CAS: 170115-33-0
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: QJURELMGBFBQCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  82.56
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-Methyl-3-(pyridine-2-carbonyl)-succinic acid 4-tert-butyl ester 1-methyl ester 在 lithium hydroxide 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 2-Methyl-4-(2-pyridyl)-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
• 作为产物：
  描述：

  methyl (S)-2-[(trifluoromethanesulfonyl)oxy]propionate 、 3-氧代-3-(2-吡啶基)丙酸叔丁酯 在 sodium hydride 作用下， 生成 2-Methyl-3-(pyridine-2-carbonyl)-succinic acid 4-tert-butyl ester 1-methyl ester
  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