4(S)-ethyl 4-(3-benzyloxacarbonyl-5-oxo-1,3-oxazolidin-4-yl)-3-oxobutanoate | 258854-39-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4(S)-ethyl 4-(3-benzyloxacarbonyl-5-oxo-1,3-oxazolidin-4-yl)-3-oxobutanoate
• 英文别名: benzyl (4S)-4-(4-ethoxy-2,4-dioxobutyl)-5-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 258854-39-6
• 化学式: C₁₇H₁₉NO₇
• 分子量: 349.34
• InChiKey: CSOLLRZPBPMEDK-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  99.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甘氨酸乙酯盐酸盐 、 4(S)-ethyl 4-(3-benzyloxacarbonyl-5-oxo-1,3-oxazolidin-4-yl)-3-oxobutanoate 在 三乙胺 作用下， 以 苯 为溶剂， 150.0 ℃ 、133.32 Pa 条件下， 反应 2.5h， 以63%的产率得到(-)-(3S,E)-3-<(Benzyloxycarbonyl)amino>-1-<(ethoxycarbonyl)methyl>-5-<(ethoxycarbonyl)methylidene>-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：

  (S)-(+)-3(苄氧羰基)-5-氧代-4-恶唑啉乙酸 在 吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 4(S)-ethyl 4-(3-benzyloxacarbonyl-5-oxo-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.