(2R,4S)-ethyl 4-(3-benzoyl-4-benzyl-5-oxo-2-phenyl-1,3-oxazolidin-4-yl) 3-oxobutanoate | 258854-43-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,4S)-ethyl 4-(3-benzoyl-4-benzyl-5-oxo-2-phenyl-1,3-oxazolidin-4-yl) 3-oxobutanoate
• 英文别名: ethyl 4-[(2R,4S)-3-benzoyl-4-benzyl-5-oxo-2-phenyl-1,3-oxazolidin-4-yl]-3-oxobutanoate
• CAS: 258854-43-2
• 化学式: C₂₉H₂₇NO₆
• 分子量: 485.536
• InChiKey: GULIJDQQBINTHN-PXJZQJOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲胺 、 (2R,4S)-ethyl 4-(3-benzoyl-4-benzyl-5-oxo-2-phenyl-1,3-oxazolidin-4-yl) 3-oxobutanoate 以 1,2-二氯乙烷 为溶剂， 150.0 ℃ 、133.32 Pa 条件下， 反应 2.5h， 以43%的产率得到(3S,E)-3-benzoylamino-3-benzyl-5-ethoxycarbonylmethylidene-1-methyl-2-pyrrolidinone
  参考文献：
  名称：

  Synthesis of Lactam-Based Peptidomimetics from β-Keto Esters and β-Keto Amides

  摘要：

  Pyrrolidinone-based peptidomimetics, in which the peptide bond is forced to adopt either a cis or trans geometry, have been prepared from readily available amino acids. Peptidomimetics based on amino acid side chain to side chain cyclization (17), side chain to N cyclization (18), and alpha-H to side chain cyclization (28) have been developed. A key step in the syntheses is the treatment of a peptide-based beta-keto ester or amide with an amine. The absolute configuration of compounds 28 was established using Seebach oxazolidinone chemistry.

  DOI：

  10.1021/jo991306v
• 作为产物：
  描述：

  (2R,4S)-tert-butyl 3-benzoyl-4-benzyl-5-oxo-2-phenyl-1,3-oxazolidin-4-yl ethanoate 在 吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.58h， 生成 (2R,4S)-ethyl 4-(3-benzoyl-4-benzyl-5-oxo-2-phenyl-1,3-oxazolidin-4-yl) 3-oxobutanoate
  参考文献：
  名称：

  Synthesis of Lactam-Based Peptidomimetics from β-Keto Esters and β-Keto Amides

  摘要：

  Pyrrolidinone-based peptidomimetics, in which the peptide bond is forced to adopt either a cis or trans geometry, have been prepared from readily available amino acids. Peptidomimetics based on amino acid side chain to side chain cyclization (17), side chain to N cyclization (18), and alpha-H to side chain cyclization (28) have been developed. A key step in the syntheses is the treatment of a peptide-based beta-keto ester or amide with an amine. The absolute configuration of compounds 28 was established using Seebach oxazolidinone chemistry.

  DOI：

  10.1021/jo991306v

文献信息

• Synthesis of Lactam-Based Peptidomimetics from β-Keto Esters and β-Keto Amides
  作者：Andrew D. Abell、James Gardiner

  DOI：10.1021/jo991306v

  日期：1999.12.1

  Pyrrolidinone-based peptidomimetics, in which the peptide bond is forced to adopt either a cis or trans geometry, have been prepared from readily available amino acids. Peptidomimetics based on amino acid side chain to side chain cyclization (17), side chain to N cyclization (18), and alpha-H to side chain cyclization (28) have been developed. A key step in the syntheses is the treatment of a peptide-based beta-keto ester or amide with an amine. The absolute configuration of compounds 28 was established using Seebach oxazolidinone chemistry.