(S)-2-tert-Butoxycarbonylamino-2-isobutyl-5-methyl-hex-4-enoic acid methyl ester | 159215-95-9

• 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: (S)-2-tert-Butoxycarbonylamino-2-isobutyl-5-methyl-hex-4-enoic acid methyl ester
• CAS: 159215-95-9
• 化学式: C₁₇H₃₁NO₄
• 分子量: 313.437
• InChiKey: RXSNIEJVRNEXBV-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-2-tert-Butoxycarbonylamino-2-isobutyl-5-methyl-hex-4-enoic acid methyl ester 在 三氟甲磺酸三甲基硅酯 、 双(三甲基硅烷基)氨基钾 、 臭氧 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 0.92h， 生成 (2S)-4-benzyl-2-[(5S)-5-(3-methylbut-2-enyl)-5-(2-methylpropyl)-4-oxo-1H-pyrrol-3-yl]-2-(2-methylpropyl)-1H-pyrrol-3-one
  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：

  prop-2-enyl (2R,4S)-2-tert-butyl-4-(3-methylbut-2-enyl)-4-(2-methylpropyl)-5-oxo-1,3-oxazolidine-3-carboxylate 在 sodium hydroxide 、 四(三苯基膦)钯 、 potassium carbonate 、 5,5-二甲基-1,3-环己二酮 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 (S)-2-tert-Butoxycarbonylamino-2-isobutyl-5-methyl-hex-4-enoic 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