dimethyl 3,6-dimethyl-pyrazine-2,5-dicarboxylate | 885-65-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: dimethyl 3,6-dimethyl-pyrazine-2,5-dicarboxylate
• 英文别名: dimethyl 3,6-dimethylpyrazine-2,5-dicarboxylate；3,6-dimethyl-pyrazine-2,5-dicarboxylic acid dimethyl ester
• CAS: 885-65-4
• 化学式: C₁₀H₁₂N₂O₄
• 分子量: 224.216
• InChiKey: SYEIZIOPUYDNGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  78.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 3,6-dimethyl-pyrazine-2,5-dicarboxylate 在 盐酸 、 sodium hydroxide 、 氯化亚砜 作用下， 反应 2.5h， 生成 3,6-dimethyl-2,5-pyrazinedicarboxylic acid chloride
  参考文献：
  名称：

  新型手性恶唑啉配体在 Rh(I) 催化的对映选择性氢化硅烷化中具有潜在的电荷转移效应

  摘要：

  新型 2-(4,4'-bipyridin-2-yl) 恶唑啉具有手性恶唑啉部分，从 4,4'-联吡啶开始合成，并在 N'-位选择性地单甲基化。在与铑配位后，这些缺电子配体应该在 Rh(I) 催化的对映选择性氢化硅烷化中表现出与供电子底物的电荷转移效应（见下一篇出版物）。与铑络合后，4,4'-联吡啶和吡嗪-双恶唑啉也有类似的效果。为了比较，合成了 2-(4-苯基吡啶-2-基)恶唑啉配体。制备并表征了选定配体的 Rh(I)-配合物，包括 X 射线结构分析。

  DOI：

  10.1002/(sici)1099-0682(199806)1998:6<771::aid-ejic771>3.0.co;2-y
• 作为产物：
  描述：

  3,6-二甲基-2,5-吡嗪二甲醇 在 potassium permanganate 、 硫酸 作用下， 以 水 为溶剂， 反应 4.0h， 生成 dimethyl 3,6-dimethyl-pyrazine-2,5-dicarboxylate
  参考文献：
  名称：

  Synthesis and positive inotropic activity evaluation of liguzinediol metabolites

  摘要：

  2,5-Dihydroxymethyl-3,6-dimethylpyrazine (liguzinediol) has been recently discovered as a potential agent for treatment of heart failure with low safety risk. In the present study, four main metabolites of liguzinediol were synthesized and their positive inotropic activities were evaluated. Synthetic compounds were identical with the isolated metabolites of liguzinediol. Pharmacological examinations showed that the four major metabolites were not observed positive inotropic activity, and revealed that the positive inotropic activity of liguzinediol was essentially attributed to the parent agent. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.072

文献信息

• Studies on Pyrazines; 21.¹A Convenient Synthesis of Pyrazinecarboxylic Acid Derivatives from Chloropyrazines
  作者：Ryo Takeuchi、Katsunobu Suzuki、Nobuhiro Sato

  DOI：10.1055/s-1990-27055

  日期：——

  Palladium-catalyzed carbonylation of chloropyrazines in methanol led to pyrazinecarboxylic esters in good yields. Similarly, pyrazinecarboxamides were obtained by using dialkylamines or alkylamines as the solvent.

  在甲醇中，以钯催化的氯吡嗪羰基化反应生成了产量良好的吡嗪羧酸酯。同样，使用二烷基胺或烷基胺作为溶剂也成功获得了吡嗪羧酸胺。
• The synthesis of imidazoline analogs of the kainoid family
  作者：Hansruedi Baumgartner、Anthony C. O'Sullivan

  DOI：10.1016/s0040-4020(97)00005-7

  日期：1997.2

  insecticidal activties of kainic 1 and domoic 2 acids with compounds of simpler structure and much easier accessibility, the highly functionalised imidazolines 4, 27 and 28 were prepared. This involved a synthesis of suitably protected β-aminoglutamic acid derivatives as key intermediates, which were condensed with orthoesters and deprotected to yield the desired compounds.

  在努力模拟物红藻驱虫和杀虫工作之外的活动1和软骨藻2个羧酸与和容易得多无障碍简单的结构的化合物中，高度官能化咪唑啉4，27和28制备。这涉及适当保护的β-氨基谷氨酸衍生物作为关键中间体的合成，将其与原酸酯缩合并脱保护得到所需化合物。
• Synthesis of pyrazine via chemoselective reduction of β-keto-α-oximino ester using baker’s yeast
  作者：Kilwoong Mo、Jin Hyeong Park、Soon Bang Kang、Youseung Kim、Yong Sup Lee、Jae Wook Lee、Gyochang Keum

  DOI：10.1016/j.molcatb.2015.11.003

  日期：2016.1

  The synthesis of pyrazines by the baker's yeast-mediated reaction of beta-keto-alpha-oximino esters and amides is described. Baker's yeast reduced oximes selectively over ketones of beta-keto-alpha-oximino esters to give the corresponding beta-keto-alpha-amino ester intermediates, which underwent spontaneous dimerization followed by air-induced aromatization to yield pyrazines. The chemoselective reduction of beta-keto-alpha-oximino amides using baker's yeast also afforded the corresponding pyrazines. Interestingly, both hydroximes and alkoximes gave the pyrazines by the baker's yeast-mediated reduction via the corresponding amino ketones, the known precursors of pyrazines. The reaction was strongly dependent upon pH of reaction medium, and gave optimum yields at pH 5. These results demonstrate that pyrazines were synthesized efficiently and eco-friendly using a whole-cell biocatalytic system as an alternative to chemical reduction. (C) 2015 Elsevier B.V. All rights reserved.
• Zercher, Charles K.; Miller, Marvin J., Heterocycles, 1988, vol. 27, # 5, p. 1123 - 1126
  作者：Zercher, Charles K.、Miller, Marvin J.

  DOI：——

  日期：——
• Diaquabis(5-methoxycarbonyl-3,6-dimethylpyrazine-2-carboxylato-<i>N</i>¹,<i>O</i>)copper(II)
  作者：Y. Wang、H. Stoeckli-Evans

  DOI：10.1107/s0108270197015643

  日期：1998.3.15

  The reaction of the bis(methyl ester) of 3,6-dimethylpyrazine-2,5-dicarboxylic acid with copper perchlorate leads to the formation of the centrosymmetric mononuclear complex [Cu(C9H9N2O4)(2)(H2O)(2)]. Two partially hydrolysed (ionized) ligands are coordinated, in a bidentate fashion, to the Cu atom. The Cu coordination sphere is completed by two water molecules, Symmetry-related molecules are linked by a strong hydrogen bond, involving the carbonyl O atom of the carboxylato group and the coordinated water molecules, to form a two-dimensional network.