(2R,4R)-4-Benzyl-2-tert-butyl-4-(3-methyl-but-2-enyl)-5-oxo-oxazolidine-3-carboxylic acid allyl ester | 147240-32-2

• 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: (2R,4R)-4-Benzyl-2-tert-butyl-4-(3-methyl-but-2-enyl)-5-oxo-oxazolidine-3-carboxylic acid allyl ester
• CAS: 147240-32-2
• 化学式: C₂₃H₃₁NO₄
• 分子量: 385.503
• InChiKey: IHJRNWYDTXJVPM-AUSIDOKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 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：
  0.48
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,4R)-4-Benzyl-2-tert-butyl-4-(3-methyl-but-2-enyl)-5-oxo-oxazolidine-3-carboxylic acid allyl ester 在 sodium hydroxide 、 sodium periodate 、 四氧化锇 、 四(三苯基膦)钯 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 5,5-二甲基-1,3-环己二酮 、 臭氧 、 N-甲基吗啉氧化物 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 74.59h， 生成 (S)-2-tert-Butoxycarbonylamino-2-[(2S,5'S)-5'-isobutyl-2-isopropyl-5'-(3-methyl-but-2-enyl)-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-4-yl]-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  De Novo Design, Synthesis, and X-ray Crystal Structures of Pyrrolinone-Based .beta.-Strand Peptidomimetics

  摘要：

  The de novo design and synthesis of a novel non-peptide scaffolding for beta-strand/sheet mimics are described. The scaffold consists of repeating 3,5,5-trisubstituted pyrrolinone (enaminone) units punctuated with appropriate amino acid side chains. The iterative construction of the pyrrolinones exploits a highly efficient cyclization of metalloimines, the latter derived from C-terminal aldehydes and readily available alpha-substituted alpha-amino ester building blocks. As predicted by interactive computer modeling and confirmed by X-ray crystallography, the polypyrrolinones present the side chains and carbonyl hydrogen-bond accepters in a solid-state conformation which mimics polypeptide beta-sheets. Importantly, the enaminone NH protons form hydrogen bonds both intramolecularly, stabilizing the beta-strand conformation, and intermolecularly, promoting sheet formation. The presence or absence of the nitrogen protecting group controlled antiparallel versus parallel sheet formation.

  DOI：

  10.1021/ja00101a017
• 作为产物：
  描述：

  特戊醛 在 sodium hydroxide 、 双(三甲基硅烷基)氨基钾 作用下， 以 二氯甲烷 为溶剂， 反应 433.25h， 生成 (2R,4R)-4-Benzyl-2-tert-butyl-4-(3-methyl-but-2-enyl)-5-oxo-oxazolidine-3-carboxylic acid allyl ester
  参考文献：
  名称：

  De Novo Design, Synthesis, and X-ray Crystal Structures of Pyrrolinone-Based .beta.-Strand Peptidomimetics

  摘要：

  The de novo design and synthesis of a novel non-peptide scaffolding for beta-strand/sheet mimics are described. The scaffold consists of repeating 3,5,5-trisubstituted pyrrolinone (enaminone) units punctuated with appropriate amino acid side chains. The iterative construction of the pyrrolinones exploits a highly efficient cyclization of metalloimines, the latter derived from C-terminal aldehydes and readily available alpha-substituted alpha-amino ester building blocks. As predicted by interactive computer modeling and confirmed by X-ray crystallography, the polypyrrolinones present the side chains and carbonyl hydrogen-bond accepters in a solid-state conformation which mimics polypeptide beta-sheets. Importantly, the enaminone NH protons form hydrogen bonds both intramolecularly, stabilizing the beta-strand conformation, and intermolecularly, promoting sheet formation. The presence or absence of the nitrogen protecting group controlled antiparallel versus parallel sheet formation.

  DOI：

  10.1021/ja00101a017

文献信息

• An effective synthesis of scalemic 3,5,5-trisubstituted pyrrolin-4-ones
  作者：Amos B. Smith、Ryan C. Holcomb、Mark C. Guzman、Terence P. Keenan、Paul A. Sprengeler、Ralph Hirschmann

  DOI：10.1016/s0040-4039(00)60058-8

  日期：1993.1

  A new two-step method employs the intramolecular cyclization of metalated imino esters for the construction of scalemic 3,5,5-trisubstituted pyrrolin-4-ones (4). The imino esters in turn derive from alpha-disubstituted amino acids, the latter readily available via a new protocol exploiting the enantioretentive alkylation of oxazolidinones.