2-[(2R,4S)-3-benzoyl-4-benzyl-5-oxo-2-phenyl-1,3-oxazolidin-4-yl]acetyl chloride | 179910-98-6

• 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: 2-[(2R,4S)-3-benzoyl-4-benzyl-5-oxo-2-phenyl-1,3-oxazolidin-4-yl]acetyl chloride
• CAS: 179910-98-6
• 化学式: C₂₅H₂₀ClNO₄
• 分子量: 433.891
• InChiKey: TWZZLOYPWLUMFF-NOZRDPDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(2R,4S)-3-benzoyl-4-benzyl-5-oxo-2-phenyl-1,3-oxazolidin-4-yl]acetyl chloride 在 吡啶 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 150.0 ℃ 、133.32 Pa 条件下， 反应 5.0h， 生成 (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)-3-benzoyl-4-benzyl-2-phenyloxazolidin-5-one 在 草酰氯 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.08h， 生成 2-[(2R,4S)-3-benzoyl-4-benzyl-5-oxo-2-phenyl-1,3-oxazolidin-4-yl]acetyl chloride
  参考文献：
  名称：

  Self-addition products from the alkylation of amino acid-derived oxazolidinones: X-ray molecular structures of (2R,4S,1′S)-3-benzoyl-4-[benzoylamino(phenyl)methyl]-4-benzyl-2-phenyl-1,3-oxazolidin-5-one, (2R,4S,1′S)- and (2R,4S,1′R)-3-benzoyl-4-[benzoylamino(phenyl)methyl]-4-isopropyl-2-phenyl-1,3-oxazolidin-5-one

  摘要：

  The alkylation of (2R,4S)-3-benzoyl-4-benzyl-2-phenyloxazolidin-5-one 7 with diphenylmethyl bromoacetate proceeded with high diastereoselectivity, and the resulting product was hydrolysed to give [(2'R,4'S)-3'-benzoyl-4'-benzyl-5'-oxo-2'-phenyloxazolidin-4'-yl]acetic acid 9. The self-addition byproduct (2R,4S, 1'S)-3-benzoyl-4-[benzoylamino(phenyl)methyl] -4-benzyl-2-phenyl-1,3-oxazolidin-5-one 11 was also isolated. The structures of compound of 11 and the related self-addition products (2R,4S,1'S and 1'R)-3-benzoyl-4-[benzoylamino(phenyl)methyl]-4-isopropyl-2-phenyl-1,3-oxazolidin-5-one 20 and 21 were determined by X-ray crystallography. The mechanism of formation of the self-addition products is discussed.

  DOI：

  10.1039/p19960001299