1-(4-methoxybenzyl)-3,5-dichloro-6-isobutylpyrazin-2(1H)-one | 849775-01-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-methoxybenzyl)-3,5-dichloro-6-isobutylpyrazin-2(1H)-one
• 英文别名: 3,5-Dichloro-1-[(4-methoxyphenyl)methyl]-6-(2-methylpropyl)pyrazin-2-one
• CAS: 849775-01-5
• 化学式: C₁₆H₁₈Cl₂N₂O₂
• 分子量: 341.237
• InChiKey: OVLHPNTVCZRRGZ-UHFFFAOYSA-N

物化性质

• 熔点：
  118-120 °C
• 沸点：
  439.3±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  1-(4-methoxybenzyl)-3,5-dichloro-6-isobutylpyrazin-2(1H)-one 在 四(三苯基膦)钯 、 水 、 sodium formate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 110.0~135.0 ℃ 、3.55 MPa 条件下， 反应 32.0h， 生成 1-Isobutyl-2-(4-methoxy-benzyl)-2,5-diaza-bicyclo[2.2.2]octane-3,6-dione
  参考文献：
  名称：

  侧链修饰的β-turn模拟物的合成，用于修饰物质P的C末端

  摘要：

  为了进行P物质的信使区的β-转角扫描，已经从吡嗪酮合成了1型侧链适应性β-转角模拟物，其特征在于氨基哌啶酮羧酸酯支架中肽链的固定顺式构象。还描述了物质P肽类似物。

  DOI：

  10.1016/j.tetlet.2005.01.056
• 作为产物：
  描述：

  草酰氯 、 在 N,N-二甲基甲酰胺 作用下， 以55%的产率得到1-(4-methoxybenzyl)-3,5-dichloro-6-isobutylpyrazin-2(1H)-one
  参考文献：
  名称：

  侧链修饰的β-turn模拟物的合成，用于修饰物质P的C末端

  摘要：

  为了进行P物质的信使区的β-转角扫描，已经从吡嗪酮合成了1型侧链适应性β-转角模拟物，其特征在于氨基哌啶酮羧酸酯支架中肽链的固定顺式构象。还描述了物质P肽类似物。

  DOI：

  10.1016/j.tetlet.2005.01.056

文献信息

• Efficient Preparation of Tetrasubstituted Pyrazines Starting from Pyrazin-2(1H)-ones
  作者：Erik Van der Eycken、Sachin Modha、Jalpa Trivedi、Vaibhav Mehta、Denis Ermolat'ev

  DOI：10.1055/s-0031-1289714

  日期：2012.6

  methodology for the synthesis of tetrasubstituted pyrazines starting from pyrazin-2(1H)-ones has been elaborated. Diversity in the functionalization and the beneficial effect of microwave irradiation throughout the methodology has been demonstrated. palladium catalysis - copper catalysis - pyrazines - 3,5-dichloropyrazin-2(1H)-ones - microwaves - nucleosides

  已经阐述了一种从吡嗪-2（1 H）-ones开始合成四取代吡嗪的有效方法。在整个方法中，微波辐射的功能化和有益作用的多样性已得到证明。 钯催化-铜催化-吡嗪-3,5-二氯吡嗪-2（1 H）-ones-微波-核苷
• A facile diversity-oriented synthesis of imidazo[1,2-a]pyrazinones via gold-catalyzed regioselective heteroannulation of propynylaminopyrazinones
  作者：Dipak D. Vachhani、Sachin G. Modha、Abhishek Sharma、Erik V. Van der Eycken

  DOI：10.1016/j.tet.2012.10.019

  日期：2013.1

  A gold-catalyzed regioselective heteroannulation strategy has been developed for the concise and efficient synthesis of imidazo[1,2-a]pyrazinones. The protocol allows the introduction of diversity via the application of substituted propargyl amines or via Suzuki-coupling of the generated imidazo[1,2-a]pyrazinones with various (het)aryl boronic acids.

  已经开发了一种金催化的区域选择性异环化策略，用于简洁有效地合成咪唑并[1,2- a ]吡嗪酮。该协议允许通过应用取代的炔丙基胺或通过将生成的咪唑并[1,2- a ]吡嗪酮与各种（杂）芳基硼酸进行铃木偶联来引入多样性。
• An Expeditious Route toward Pyrazine-Containing Nucleoside Analogues
  作者：Sachin G. Modha、Jalpa C. Trivedi、Vaibhav P. Mehta、Denis S. Ermolat’ev、Erik V. Van der Eycken

  DOI：10.1021/jo102089h

  日期：2011.2.4

  An improved and convenient methodology for the synthesis of asymmetrically substituted pyrazines starting from 3,5-dichloropyrazin-2(1H)-ones has been elaborated. Several nucleoside analogues have been synthesized containing the pyrazine core as the organic base coupled with the sugar via a triazole linkage. The beneficial effect of microwave irradiation throughout the sequence has been demonstrated.
• <i>N</i>-Heterocyclic Carbene Catalyzed Aroylation of 3,5-Dichloro-2(1<i>H</i>)-pyrazinones
  作者：Vaibhav P. Mehta、Ajendra kumar Sharma、Sachin G. Modha、Sweta Sharma、Thirumal Meganathan、Virinder Singh Parmar、Erik Van der Eycken

  DOI：10.1021/jo200155n

  日期：2011.4.15

  The N-heterocyclic carbene catalyzed chemoselective C3-aroylation of 3,5-dichloro-2(1H)-pyrazinones with various aldehydes is reported. We herein describe results of this remarkable mild and efficient procedure.
• Synthesis of functionalized furopyrazines as restricted dipeptidomimetics
  作者：Stijn Claerhout、Sweta Sharma、Christian Sköld、Claudia Cavaluzzo、Anja Sandström、Mats Larhed、Meganathan Thirumal、Virinder S. Parmar、Erik V. Van der Eycken

  DOI：10.1016/j.tet.2012.02.022

  日期：2012.4

  Herein, an efficient synthetic approach to a furopyrazine scaffold with four points of diversity, starting from 2(1H)-pyrazinones, with dipeptomimetic properties, is presented. R-groups corresponding to amino acid side chains were introduced during the 2(1H)-pyrazinone and subsequent furopyrazine formation. The furopyrazine scaffold was further functionalized with an amino- and a carboxy-terminus resulting in a conformationally restricted dipeptidomimetic scaffold. The carboxy-terminus was introduced via a chemoselective vinylation of the 7-position followed by oxidative cleavage, while the amino-terminus was obtained via Buchwald-Hartwig amidation of the 2-position of the scaffold. The versatility of the synthetic method was demonstrated by the synthesis of a small library of diversely substituted furopyrazines having various amino acid side chains on the four points of diversity. Evaluation with an X-ray structure of the scaffold and computational analysis supports the exploitation of the furopyrazine scaffold as a restricted dipeptide mimic, which can mimic the two central residues of a beta-turn. (C) 2012 Elsevier Ltd. All rights reserved.