(-)-(3S,E)-3-<(Benzyloxycarbonyl)amino>-1-<(ethoxycarbonyl)methyl>-5-<(ethoxycarbonyl)methylidene>-2-pyrrolidinone

• 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: (-)-(3S,E)-3-<(Benzyloxycarbonyl)amino>-1-<(ethoxycarbonyl)methyl>-5-<(ethoxycarbonyl)methylidene>-2-pyrrolidinone
• 英文别名: (3S,E)-3-benzyloxycarbonylamino-1-ethoxycarbonylmethyl-5-ethoxycarbonylmethylidene-2-pyrrolidinone；ethyl 2-[(3S,5E)-3-(benzyloxycarbonylamino)-5-(2-ethoxy-2-oxo-ethylidene)-2-oxo-pyrrolidin-1-yl]acetate；ethyl 2-[(3S,5E)-5-(2-ethoxy-2-oxoethylidene)-2-oxo-3-(phenylmethoxycarbonylamino)pyrrolidin-1-yl]acetate
• 化学式: C₂₀H₂₄N₂O₇
• 分子量: 404.42
• InChiKey: XAAAXTXCGNLCGN-SFKKXYGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (S)-(+)-3(苄氧羰基)-5-氧代-4-恶唑啉乙酸 在 对甲苯磺酸 sodium hydroxide 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 91.0h， 生成 (-)-(3S,E)-3-<(Benzyloxycarbonyl)amino>-1-<(ethoxycarbonyl)methyl>-5-<(ethoxycarbonyl)methylidene>-2-pyrrolidinone
  参考文献：
  名称：

  Synthesis of Cyclic Acylated Enamino Esters from Enol Lactones, 4-Keto amides, and 5-Hydroxy Lactams

  摘要：

  Enol lactones react with an amine to give either a keto amide or a hydroxy lactam under mild conditions. Subsequent dehydration with p-toluenesulfonic acid (PTSA) gives a cyclic acylated enamino ester in good yield (Tables 1 and 2, Schemes 2 and 4). The key prostaglandin analog precursor 18 and the gly-gly dipeptide analogs 26a and 26b were prepared using the reported conditions. Acetylation of the chloro hydroxy lactam 31, prepared from the chloro enol lactones 29, followed by elimination of acetic acid gave the chloro acylated enamino esters 28.

  DOI：

  10.1021/jo00110a026

文献信息

• Synthesis of Cyclic Acylated Enamino Esters from Enol Lactones, 4-Keto amides, and 5-Hydroxy Lactams
  作者：A. D. Abell、M. D. Oldham、J. M. Taylor

  DOI：10.1021/jo00110a026

  日期：1995.3

  Enol lactones react with an amine to give either a keto amide or a hydroxy lactam under mild conditions. Subsequent dehydration with p-toluenesulfonic acid (PTSA) gives a cyclic acylated enamino ester in good yield (Tables 1 and 2, Schemes 2 and 4). The key prostaglandin analog precursor 18 and the gly-gly dipeptide analogs 26a and 26b were prepared using the reported conditions. Acetylation of the chloro hydroxy lactam 31, prepared from the chloro enol lactones 29, followed by elimination of acetic acid gave the chloro acylated enamino esters 28.
• 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.