[(S)-1-((R)-5-Benzyl-5-methyl-4-oxo-4,5-dihydro-1H-pyrrol-2-yl)-1-hydroxymethyl-2-methyl-propyl]-carbamic acid tert-butyl ester | 181861-95-0

• 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: [(S)-1-((R)-5-Benzyl-5-methyl-4-oxo-4,5-dihydro-1H-pyrrol-2-yl)-1-hydroxymethyl-2-methyl-propyl]-carbamic acid tert-butyl ester
• CAS: 181861-95-0
• 化学式: C₂₂H₃₂N₂O₄
• 分子量: 388.507
• InChiKey: MAJBVLOKRBTEBV-YADHBBJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  87.66
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [(S)-1-((R)-5-Benzyl-5-methyl-4-oxo-4,5-dihydro-1H-pyrrol-2-yl)-1-hydroxymethyl-2-methyl-propyl]-carbamic acid tert-butyl ester 在 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 [(S)-1-((R)-5-Benzyl-5-methyl-4-oxo-4,5-dihydro-1H-pyrrol-2-yl)-1-formyl-2-methyl-propyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  The design and synthesis of 2,5-linked pyrrolinones. A potential non-peptide peptidomimetic scaffold

  摘要：

  The de novo design and initial synthetic studies directed toward construction of a novel non-peptide scaffold for beta-strand/sheet and related secondary peptide structural mimics are described. The scaffold, consisting of a repeating array of 2,5,5-trisubstituted pyrrolinone (enaminone) units punctuated with appropriate amino acid side chains, is conceptually related to our previously successful 3,5-linked polypyrrolinone non-peptide peptidomimetic scaffold. Construction of the 2,5,5-trisubstituted pyrrolinone ring system proceeds via intramolecular condensation of an N-protected amino dione. The latter is prepared from a protected cl-amino ketone and aldehyde via an aldol-oxidation reaction sequence. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00094-6
• 作为产物：
  描述：

  (R)-4-Benzyloxymethyl-4-isopropyl-2,5-dioxo-oxazolidine-3-carboxylic acid tert-butyl ester 在 palladium dihydroxide 、 palladium on activated charcoal 吡啶 、 sodium tetrahydroborate 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 A molecular sieve 、 氢气 、 戴斯-马丁氧化剂 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 35.5h， 生成 [(S)-1-((R)-5-Benzyl-5-methyl-4-oxo-4,5-dihydro-1H-pyrrol-2-yl)-1-hydroxymethyl-2-methyl-propyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  The design and synthesis of 2,5-linked pyrrolinones. A potential non-peptide peptidomimetic scaffold

  摘要：

  The de novo design and initial synthetic studies directed toward construction of a novel non-peptide scaffold for beta-strand/sheet and related secondary peptide structural mimics are described. The scaffold, consisting of a repeating array of 2,5,5-trisubstituted pyrrolinone (enaminone) units punctuated with appropriate amino acid side chains, is conceptually related to our previously successful 3,5-linked polypyrrolinone non-peptide peptidomimetic scaffold. Construction of the 2,5,5-trisubstituted pyrrolinone ring system proceeds via intramolecular condensation of an N-protected amino dione. The latter is prepared from a protected cl-amino ketone and aldehyde via an aldol-oxidation reaction sequence. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00094-6