(2R,4S)-3-benzoyl-4-benzyl-2-phenyloxazolidin-5-one | 113806-30-7

• 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: (2R,4S)-3-benzoyl-4-benzyl-2-phenyloxazolidin-5-one
• 英文别名: (2R,4S)-3-benzoyl-4-benzyl-2-phenyl-1,3-oxazolidin-5-one
• CAS: 113806-30-7
• 化学式: C₂₃H₁₉NO₃
• 分子量: 357.409
• InChiKey: ZQIYMSGCSHJWRW-RBBKRZOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,4S)-3-benzoyl-4-benzyl-2-phenyloxazolidin-5-one 在 吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.7h， 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
• 作为产物：
  描述：

  L-phenylalanine sodium salt 、 苯甲醛 、 氯化苄 以88%的产率得到
  参考文献：
  名称：

  FADEL, A.;SALAUN, J., TETRAHEDRON LETT., 28,(1987) N 20, 2243-2246

  摘要：

  DOI：

文献信息

• 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
  作者：Andrew D. Abell、Jane M. Taylor、Mark D. Oldham

  DOI：10.1039/p19960001299

  日期：——

  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.
• Synthesis and X-ray structure of a 1,2,3,6-tetrahydropyridine-based phenylalanine mimetic
  作者：Andrew D. Abell、James Gardiner、Andrew J. Phillips、Ward T. Robinson

  DOI：10.1016/s0040-4039(98)02125-x

  日期：1998.12

  A ring-closing metathesis reaction on methyl (2R)-(N-allyl-N-benzoylamino)-2-benzylpent-4-enoate 5, prepared as a single isomer from L-phenylalanine, gave a conformationally restricted 1,2,3,6-tetrahydropyridine-based phenylalanine mimetic 6 in good yield. The solid state conformation of which was determined by X-ray crystallography. (C) 1998 Elsevier Science Ltd. All rights reserved.
• A diastereoselective synthesis of the tetrahydropyridazinone core of 2-oxo-1,6-diazobicyclo[4.3.0]nonane-9-carboxylate-based peptidomimetics starting from (S)-phenylalanine
  作者：James Gardiner、Andrew D. Abell

  DOI：10.1016/s0040-4039(03)00882-7

  日期：2003.5

  A diastereoseletvive synthesis of a peptidic tetrahydropyridazinone 10 from (S)-phenylalanine is reported. This derivative was then converted to the bicyclic peptidomimetic 11, an important class of beta-strand mimetic. (C) 2003 Elsevier Science Ltd. All rights reserved.
• FADEL, A.;SALAUN, J., TETRAHEDRON LETT., 28,(1987) N 20, 2243-2246
  作者：FADEL, A.、SALAUN, J.

  DOI：——

  日期：——
• 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.