3,5-dichloro-6-isopropyl-1-(4-methoxybenzyl)-2(1H)-pyrazinone | 817575-37-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-dichloro-6-isopropyl-1-(4-methoxybenzyl)-2(1H)-pyrazinone
• 英文别名: 3,5-Dichloro-1-[(4-methoxyphenyl)methyl]-6-propan-2-ylpyrazin-2-one；3,5-dichloro-1-[(4-methoxyphenyl)methyl]-6-propan-2-ylpyrazin-2-one
• CAS: 817575-37-4
• 化学式: C₁₅H₁₆Cl₂N₂O₂
• 分子量: 327.21
• InChiKey: AWIQWRJTQSVMPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-dichloro-6-isopropyl-1-(4-methoxybenzyl)-2(1H)-pyrazinone 在 air moisture 作用下， 以 四氢呋喃 、 氯仿 、 甲苯 为溶剂， -78.0~135.0 ℃ 、3.34 MPa 条件下， 生成 2-[(4-Methoxyphenyl)methyl]-4-methyl-1-propan-2-yl-2,5-diazabicyclo[2.2.2]octane-3,6-dione
  参考文献：
  名称：

  Acid catalysed methanolysis of 2,5-diazabicyclo[2.2.2]octane-3,6-diones: scope and limitations

  摘要：

  The selective methanolysis of 2,5-diazabicyclo[2.2.2]octane-3,6-dione systems is a key step in a synthetic procedure leading to 4-amino-6-oxo-2-piperidinecarboxylate systems. This reaction seems to be primarily governed by steric hindrance caused by the substituents at the 1 - and 4-bridgehead positions of the dione. In absence of bulky substituents the methanolysis is directed by the secondary or tertiary nature of the two lactam moieties. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.186
• 作为产物：
  描述：

  草酰氯 、 2-(4-methoxybenzylamino)-3-methylbutyronitrile 在 三乙胺盐酸盐 、 N,N-二甲基甲酰胺 作用下， 以 氯苯 为溶剂， 反应 52.0h， 生成 3,5-dichloro-6-isopropyl-1-(4-methoxybenzyl)-2(1H)-pyrazinone
  参考文献：
  名称：

  Design and synthesis of novel type VI-like β-turn mimetics. Diversity at the i+1 and the i+2 position

  摘要：

  In this paper, a synthetic approach for functionalised 5-aminopiperidinone-2-carboxylate (APC) systems as non-pro cis-peptide bond containing external beta-turn mimics is presented. The scope and limitations of the synthetic method are discussed and the potential turn inducing properties of a model compound are evaluated by means of molecular modelling and NMR analysis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.054

文献信息

• Development of New Amino(oxo)piperidinecarboxylate Scaffolds and Their Evaluation as -Turn Mimics
  作者：Bie M. P. Verbist、Wim M. De Borggraeve、Suzanne Toppet、Frans Compernolle、Georges J. Hoornaert

  DOI：10.1002/ejoc.200500036

  日期：2005.7

  In this paper a synthetic approach for functionalised bicyclic Amino(oxo)piperidinecarboxylate (APC) systems is presented. These systems can potentially be applied as cis-peptide bond containing β-turn mimics. The scope and limitations of the synthetic method are discussed and the turn-inducing properties of a model compound are evaluated by means of molecular modelling and NMR analysis. (© Wiley-VCH

  在本文中，提出了功能化双环氨基（氧代）哌啶羧酸 (APC) 系统的合成方法。这些系统有可能用作含有 β-转角模拟物的顺式肽键。讨论了合成方法的范围和局限性，并通过分子建模和 NMR 分析评估了模型化合物的转向诱导特性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)