6-氧代-1,6-二氢-2,3-吡嗪二甲腈 | 57005-60-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 6-氧代-1,6-二氢-2,3-吡嗪二甲腈
• 英文名称: 1,6-dihydro-6-oxo-2,3-pyrazinedicarbonitrile
• 英文别名: 6-Oxo-1,6-dihydropyrazine-2,3-dicarbonitrile；6-oxo-1H-pyrazine-2,3-dicarbonitrile
• CAS: 57005-60-4
• 化学式: C₆H₂N₄O
• mdl: MFCD10697780
• 分子量: 146.108
• InChiKey: MQZGOHPDJLBDAP-UHFFFAOYSA-N

物化性质

• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-氧代-1,6-二氢-2,3-吡嗪二甲腈 在 吡啶 、 sodium hydroxide 、 三氯氧磷 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 生成 5-(4-chloro-3-methyl-phenoxy)-pyrazine-2,3-dicarbonitrile
  参考文献：
  名称：

  Nakamura, Akira; Ataka, Toshiei; Segawa, Hirozo, Agricultural and Biological Chemistry, 1983, vol. 47, # 7, p. 1555 - 1560

  摘要：

  DOI：
• 作为产物：
  描述：

  乙醛酸 、 二氨基马来腈 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 6-氧代-1,6-二氢-2,3-吡嗪二甲腈
  参考文献：
  名称：

  Nakamura, Akira; Ataka, Toshiei; Segawa, Hirozo, Agricultural and Biological Chemistry, 1983, vol. 47, # 7, p. 1561 - 1568

  摘要：

  DOI：

文献信息

• OFF-ON-OFF Red-Emitting Fluorescent Indicators for a Narrow pH Window
  作者：Antonin Cidlina、Miroslav Miletin、Mahtab Fathi-Rasekh、Victor N. Nemykin、Petr Zimcik、Veronika Novakova

  DOI：10.1002/chem.201604978

  日期：2017.2.3

  measurements, and further supported by theoretical calculations (DFT, TDDFT). The pH‐sensing properties of the TPyzPzs have been investigated in THF and in water after anchoring the TPyzPzs to liposomes. The salient pKa values were around 1.3 (azomethine nitrogen) and 2.29–4.76 (donor for ICT). The lead indicators (sensing over a pH range of 1.0–2.5) with fairly steep sensing profiles exhibited increases in

  荧光猝灭的两个独立机制的独特组合，即来自外围供体的分子内电荷转移（ICT）和四吡嗪并卟啉锌（TPyzPz）中的甲亚胺氮原子的质子化，为检测特定范围内的pH提供了新的可能性。pH选择性受ICT供体的不同碱性（二甲基氨基芳基）的控制，而ICT通过不同长度的π延伸接头与大环连接。ICT和质子化已通过光物理，光谱（UV / Vis和MCD光谱）和电化学测量进行了详细研究，并得到了理论计算（DFT，TDDFT）的进一步支持。在将TPyzPzs固定在脂质体上后，已经在THF和水中对TPyzPzs的pH敏感特性进行了研究。显着性p Ka值约为1.3（甲亚胺氮）和2.29–4.76（ICT捐助者）。铅指示剂（在1.0-2.5的pH范围内检测）具有较陡的检测曲线，在OFF / ON状态之间的荧光增强了20倍以上，在红色区域有强吸收（Q波段最大值> 650 nm） ，ε ≈2×10 6 米-1 厘米-1）。
• Anticoccidials. VII. Synthesis of 4,5-dihydro-5-oxo-2-pyrazinecarboxylic acid 1-oxides.
  作者：MITSUHIKO MANO、TAKUJI SEO、KINICHI IMAI

  DOI：10.1248/cpb.28.3057

  日期：——

  Hydrolysis of 1, 6-dihydro-6-oxo-2, 3-pyrazinedicarbonitrile (4) gave sodium hydrogen 1, 6-dihydro-6-oxo-2, 3-pyrazinedicarboxylate (6), which was converted to methyl 1, 6-dihydro-6-oxo-2-pyrazinecarboxylate (10) and methyl 4, 5-dihydro-5-oxo-2-pyrazine-carboxylate (12) via a sequence of reactions including decarboxylation and esterification. Although the synthesis of 4, 5-dihydro-5-oxo-2-pyrazinecarboxylic acid 1-oxide (2) from 12 was unsuccessful, its 6-methyl derivative 3 was synthesized from the 5-methyl analog of 4.

  1, 6-二氢-6-氧代-2, 3-吡嗪二甲腈(4)的水解产物为钠氢1, 6-二氢-6-氧代-2, 3-吡嗪二羧酸盐(6)，通过一系列反应包括脱羧和酯化，将其转化为甲基1, 6-二氢-6-氧代-2-吡嗪羧酸酯(10)和甲基4, 5-二氢-5-氧代-2-吡嗪羧酸酯(12)。尽管从12合成4, 5-二氢-5-氧代-2-吡嗪羧酸1-氧化物(2)未成功，但其6-甲基衍生物3是从4的5-甲基类似物合成的。
• 2,3-Dicyanopyrazines
  申请人：Kyowa Gas Chemical Industry Co. Ltd.

  公开号：US04259489A1

  公开（公告）日：1981-03-31

  Novel 2,3-dicyanopyrazine derivatives of the formula ##STR1## wherein A represents a hydrogen atom, a lower alkyl group, an unsubstituted or substituted phenyl group, a benzyl group, or a group of the formula -ZR.sub.1 in which Z represents an oxygen or sulfur atom and R.sub.1 represents an unsubstituted or substituted lower alkyl group, a lower alkenyl group, a lower alkynyl group, an unsubstituted or substituted phenyl group, or an unsubstituted or substituted benzyl group; and B represents a halogen atom, an alkyl group containing at least 3 carbon atoms, a phenyl group having a substituent at the ortho- and/or meta-position of the benzene ring, a group of the formula ZR.sub.1 in which Z and R.sub.1 are as defined, or a group of the formula ##STR2## in which R.sub.2 and R.sub.3, independently from each other, represent a hydrogen atom, an unsubstituted or substituted lower alkyl group, a lower alkenyl group, a cycloalkyl group, an unsubstituted or substituted phenyl group, or an unsubstituted or substituted benzyl group, with the proviso that R.sub.2 and R.sub.3 do not represent a hydrogen atom at the same time, and R.sub.2 and R.sub.3 together may form a 3- to 7-membered heterocyclic ring together with the nitrogen atom to which they are bonded, said heterocyclic ring optionally containing an additional hetero atom; and processes for production thereof. These compounds have high herbicidal activity, and are useful as active ingredients of herbicides.

  2,3-二氰基吡嗪衍生物的新颖化合物，其化学式为##STR1##其中A代表氢原子、较低的烷基基团、未取代或取代的苯基团、苄基团，或者具有化学式-ZR.sub.1的基团，其中Z代表氧原子或硫原子，R.sub.1代表未取代或取代的较低烷基基团、较低烯基基团、较低炔基基团、未取代或取代的苯基团或未取代或取代的苄基团；B代表卤素原子、含有至少3个碳原子的烷基基团、苯环的邻位和/或间位有取代基的苯基团、具有已定义的Z和R.sub.1的化学式ZR.sub.1的基团，或者具有化学式##STR2##的基团，其中R.sub.2和R.sub.3分别代表氢原子、未取代或取代的较低烷基基团、较低烯基基团、环烷基基团、未取代或取代的苯基团或未取代或取代的苄基团，但R.sub.2和R.sub.3不同时代表氢原子，R.sub.2和R.sub.3共同可以与它们连接的氮原子一起形成一个3-至7-成员的杂环环，所述杂环环可选地含有一个额外的杂原子；以及其制备方法。这些化合物具有高除草活性，可用作除草剂的活性成分。
• Redesign of the Synthesis and Manufacture of an Azetidine-Bearing Pyrazine
  作者：David R. J. Hose、Phillip Hopes、Alan Steven、Christian Herber

  DOI：10.1021/acs.oprd.7b00384

  日期：2018.2.16

  Commercial route definition for a glucokinase activator called for a re-evaluation of the synthesis and processes used to access multikilogram quantities of a pyrazine building block. The processes developed allowed a literature route to sodium 6-oxo-1H-pyrazine-3-carboxylate to be leveraged. One of these processes consisted of a highly selective decarboxylation that allowed the target building block

  葡萄糖激酶激活剂的商业路线定义要求对用于获取多千克量吡嗪结构单元的合成和过程进行重新评估。所开发的方法使得可以利用文献中的方法来利用6-氧代-1 H-吡嗪-3-羧酸钠。这些过程之一是由高度选择性的脱羧作用组成的，该过程允许在标准的批处理设备中以完全的区域选择性接近目标构件。在靶中存在氮杂环丁烷环需要减轻由于使用氮杂环丁烷的盐酸盐作为输入材料而引起的杂质责任。
• 2,3-Dicyano 6 phenyl pyrazine herbicides
  申请人：Kyowa Gas Chemical Industry Co., Ltd.

  公开号：US04460403A1

  公开（公告）日：1984-07-17

  Novel 2,3-dicyanopyrazine derivatives of the formula ##STR1## wherein A represents a hydrogen atom, a lower alkyl group, an unsubstituted or substituted phenyl group, a benzyl group, or a group of the formula --ZR.sub.1 in which Z represents an oxygen or sulfur atom and R.sub.1 represents an unsubstituted or substituted lower alkyl group, a lower alkenyl group, a lower alkynyl group, an unsubstituted or substituted phenyl group, or an unsubstituted or substituted benzyl group; and B represents a halogen atom, an alkyl group containing at least 3 carbon atoms, a phenyl group having a substituent at the ortho- and/or meta-position of the benzene ring, a group of the formula ZR.sub.1 in which Z and R.sub.1 are as defined, or a group of the formula ##STR2## in which R.sub.2 and R.sub.3, independently from each other, represent a hydrogen atom, an unsubstituted or substituted lower alkyl group, a lower alkenyl group, a cycloalkyl group, an unsubstituted or substituted phenyl group, or an unsubstituted or substituted benzyl group, with the proviso that R.sub.2 and R.sub.3 do not represent a hydrogen atom at the same time, and R.sub.2 and R.sub.3 together may form a 3- to 7-membered heterocyclic ring together with the nitrogen atom to which they are bonded, said heterocyclic ring optionally containing an additional hetero atom; and processes for production thereof. These compounds have high herbicidal activity, and are useful as active ingredients of herbicides.

  化合物2,3-二氰基吡嗪衍生物的式子为##STR1##其中A代表氢原子、较低的烷基、未取代或取代的苯基、苄基或式子--ZR.sub.1的基团，其中Z代表氧原子或硫原子，R.sub.1代表未取代或取代的较低烷基、较低烯基、较低炔基、未取代或取代的苯基或未取代或取代的苄基；B代表卤原子、含有至少3个碳原子的烷基、在苯环的邻位和/或间位有取代基的苯基、式子ZR.sub.1的基团，其中Z和R.sub.1的定义如上述，或式子##STR2##其中R.sub.2和R.sub.3独立地代表氢原子、未取代或取代的较低烷基、较低烯基、环烷基、未取代或取代的苯基或未取代或取代的苄基，但要求R.sub.2和R.sub.3不能同时代表氢原子，且R.sub.2和R.sub.3可以与它们所连接的氮原子一起形成3-至7-成员的杂环，所述杂环可以选择性地包含一个额外的杂原子；以及生产这些化合物的方法。这些化合物具有高除草活性，并且可用作除草剂的活性成分。