3,5,6-三甲基-2(1H)-吡嗪酮 | 57355-08-5

• 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: 3,5,6-三甲基-2(1H)-吡嗪酮
• 英文名称: 3,5,6-trimethyl-1,2-dihydropyrazin-2-one
• 英文别名: 2-(1H)-3,5,6-trimethylpyrazinone；3,5,6-trimethyl-2(1H)-pyrazinone；3,5,6-trimethyl-1H-pyrazin-2-one；3,5,6-Trimethyl-1H-pyrazin-2-on；3,5,6-Trimethyl-2(1H)-pyrazinon；3,5,6-trimethyl-1H-pyrazin-2-one
• CAS: 57355-08-5
• 化学式: C₇H₁₀N₂O
• 分子量: 138.169
• InChiKey: XOHWPXVKBZHLQO-UHFFFAOYSA-N

物化性质

• 保留指数：
  2410

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 储存条件：
  保存在2至8°C的环境中，需要密封并保持干燥。

反应信息

• 作为反应物：
  描述：

  3,5,6-三甲基-2(1H)-吡嗪酮 在 硫酸 三氯氧磷 作用下， 反应 20.0h， 以45.9%的产率得到2-氯-3,5,6-三甲基吡嗪
  参考文献：
  名称：

  A Chiral 2-D Donor−Acceptor Array of a Bipyrazine N-Oxide and Tetracyanoethylene

  摘要：

  Hexamethylbipyrazine-N,N',N ",N'''-tetraoxide (1) is synthesized in racemic form and cocrystallized with tetracyanoethylene to give a donor-acceptor (DA) networked lattice, The resulting DA(2) cocrystal contains homochiral 2-D DA arrays (layers) cohered by 2.7 Angstrom NO ... C=C DA bonds with periplanar O p-orbital/C=C orientations, Layer formation is stereoselective, while interlayer relations yield a racemic lattice.

  DOI：

  10.1021/ol991367f
• 作为产物：
  描述：

  2-bromo-propionic acid-(1-methyl-2-oxo-propylamide) 在 氨 、 sodium iodide 作用下， 生成 3,5,6-三甲基-2(1H)-吡嗪酮
  参考文献：
  名称：

  75.吡嗪衍生物。第二部分 外消旋的2-羟基-3的合成：6-二秒。丁基吡嗪及其与脱氧抗坏血酸的关系

  摘要：

  DOI：

  10.1039/jr9470000373

文献信息

• Studies on the Mechanism of 1,2-Dihydropyrazin-2-one Ring Formation from Dipeptidyl Chloromethyl Ketone and Its Chemical Properties: Immediate Deamination during Catalytic Hydrogenation
  作者：Anna Miyazaki、Yutaka Fujisawa、Kimitaka Shiotani、Yoshio Fujita、Tingyou Li、Yuko Tsuda、Toshio Yokoi、Sharon D. Bryant、Lawrence H. Lazarus、Yoshio Okada

  DOI：10.1248/cpb.53.1152

  日期：——

  1,2-Dihydropyrazin-2-one derivatives, which have two aminoalkyl groups at the positions 3 and 6, were found to be efficient tools for the construction of potent, selective and long-acting opioid mimetics. During the course of preparation, we found that the catalytic hydrogenation of 3,6-bis(benzyloxycarbonylaminomethyl)-5-methyl-1,2-dihydropyrazin-2-one to remove the benzyloxycarbonyl groups resulted in a side reaction. By MS and NMR studies and by preparation of additional 1,2-dihydropyrazin-2-one derivatives, the structure of the by-product was identified as 3-aminomethyl-5,6-dimethyl-1,2-dihydropyrazin-2-one. Preparation of additional compounds substituted with deuterium provided us with sufficient information to confirm the structure of the product and to support a cyclization mechanism in its formation.

  在3和6位具有两个氨基烷基团的1,2-二氢吡嗪-2-酮衍生物被发现是构建强效、选择性和长效类吗啡模拟物的有效工具。在准备过程中，我们发现3,6-双(苄氧羰基氨基甲基)-5-甲基-1,2-二氢吡嗪-2-酮的催化氢化以去除苄氧羰基基团导致了副反应。通过质谱和核磁共振研究以及制备额外的1,2-二氢吡嗪-2-酮衍生物，副产物的结构被鉴定为3-氨基甲基-5,6-二甲基-1,2-二氢吡嗪-2-酮。制备含有氘的额外化合物为我们提供了足够的信息以确认产物的结构并支持其形成的环化机制。
• Pyrazines, pyrimidines and pyridazines useful in the treatment of senile
  申请人：Merck Sharp & Dohme Limited

  公开号：US05260293A1

  公开（公告）日：1993-11-09

  The present invention provides pyrazines, pyridazines or pyrimidines, or salts or prodrugs thereof, substituted on one of the ring carbon atoms thereof with a non-aromatic azacyclic or azabicyclic ring system; and independently substituted on each of the other ring carbon atoms with a substituent of low lipophilicity or a hydrocarbon substituent; which compounds stimulate central muscarinic acetylcholine receptors and therefore are useful in the treatment of neurological and mental illnesses.

  本发明提供了吡啶、吡啶嗪或嘧啶，或其盐或前药，其中其中一个环碳原子上取代为非芳香性氮杂环或氮杂双环系统；并且独立地，在其他每个环碳原子上取代为低亲脂性取代基或烃取代基；这些化合物刺激中枢胆碱能受体，因此在治疗神经和精神疾病中是有用的。
• 2-substituted alkoxy-3-substituted-pyrazines
  申请人：Toyo Jozo Kabushiki Kaisha

  公开号：US04894453A1

  公开（公告）日：1990-01-16

  A compound of the formula ##STR1## wherein Q is --CO-- or --CH.sub.2 --, R is hydroxyl, lower alkoxy, halogen, --NH-lower alkylene-OH, --NH-lower alkylene-arylthio, --NH-lower alkylene-halogen, ##STR2## in which ##STR3## is dilower alkylamino, cycloalkylamino, morpholino, ##STR4## in which R.sub.9 is hydrogen, lower alkyl or aryl, R.sub.10 is hydrogen, lower alkyl, hydroxy-lower alkyl, hydroxy-lower alkoxy-lower alkyl or di(aryl)-lower alkyl, m is an integer from 4 to 6, n is 2 or 3, R.sub.1 is alkyl or aryl-lower alkyl, R.sub.2 and R.sub.3 are each lower alkyl, or together form tetramethylene, and R.sub.4 is hydrogen, lower alkyl or aryl, in which aryl is phenyl which is optionally substituted with a group selected from the group consisting of 1-3 halogen, nitro, lower alkyl and lower alkoxy, or a pharmaceutically acceptable salt thereof, inhibits blood platelet aggregation, has vasodilating activity and inhibits lipoperoxide generation.

  一种化合物的分子式为##STR1##，其中Q为--CO--或--CH.sub.2--，R为羟基，低烷氧基，卤素，--NH-较低烷基-羟基，--NH-较低烷基-芳硫基，--NH-较低烷基-卤素，##STR2##其中##STR3##为二烷基氨基，环烷基氨基，吗啡啉，##STR4##其中R.sub.9为氢，低烷基或芳基，R.sub.10为氢，低烷基，羟基-低烷基，羟基-低烷氧基-低烷基或二(芳基)-低烷基，m为4至6的整数，n为2或3，R.sub.1为烷基或芳基-低烷基，R.sub.2和R.sub.3分别为低烷基，或者一起形成四亚甲基，R.sub.4为氢，低烷基或芳基，其中芳基为苯基，可以选择地取代为来自1-3卤素，硝基，低烷基和低烷氧基的群，或其药用盐，抑制血小板聚集，具有扩张血管活性并抑制脂质过氧化物生成。
• 1-substituted alkyl-1,2-dihydro-2-pyrazinone derivatives
  申请人：Toyo Jozo Kabushiki Kaisha

  公开号：US04837319A1

  公开（公告）日：1989-06-06

  1-Substituted alkyl-1,2-dihydro-2-pyrazinone derivatives of the formula ##STR1## wherein A is lower alkyl; R.sub.1 is selected from the group consisting of alkyl, phenyl-lower alkyl, and substituted phenyl-lower alkyl; R.sub.2 and R.sub.3 are each lower alkyl, or together form tetramethylene and R is selected from the group consisting of hydroxyl, hologen, lower alkanoyloxy R.sub.4 -carbamoyloxy, arylthio, 1-methyltetrazole-5-yl-thio, 1-imidazole, morpholino, ##STR2## in which R.sub.4 is lower alkyl or aryl, R.sub.5 is lhydrogen, lower alkyl or aryl, R.sub.6 is hydrogen, lower alkyl, hydroxy-lower alkyl, aryl, aryl-lower alkanoyl, arylcarbonyl, arylsulfonyl or thienyl-lower alkanoyl, Ar is phenyl or phenyl substituted with C.sub.1-3 alkyl, halogen, nitro, or lower alkoxy, A, R.sub.1, R.sub.2 and R.sub.3 are as defined above, m is an integer from 4-6, and n is 2 or 3; and pharmaceutically acceptable salts thereof. The compounds are useful as agents for platelet aggregation inhibition, vasodilation and anti-lipoperoxide generation.

  公式为## STR1 ##的1-取代烷基-1,2-二氢-2-吡嗪酮衍生物，其中A为低烷基; R.sub.1选择自烷基、苯基-低烷基和取代苯基-低烷基的群; R.sub.2和R.sub.3分别是低烷基，或者共同形成四亚甲基，R选择自羟基、卤素、低烷酰氧R.sub.4-氨基甲酸酯、芳基硫、1-甲基四氮唑-5-基硫、1-咪唑、吗啉、## STR2 ##其中R.sub.4是低烷基或芳基，R.sub.5是氢、低烷基或芳基，R.sub.6是氢、低烷基、羟基-低烷基、芳基、芳基-低烷酰基、芳基羰基、芳基磺酰基或噻吩基-低烷酰基，Ar是苯基或取代有C.sub.1-3烷基、卤素、硝基或低烷氧基的苯基，A、R.sub.1、R.sub.2和R.sub.3如上所定义，m为4-6的整数，n为2或3；以及其药学上可接受的盐。该化合物用作抑制血小板聚集、扩张血管和抗脂质过氧化物生成的药剂。
• Method for cancer treatment, carcinogenesis suppression or mitigation of adverse reactions of anticancer agents
  申请人：Fujii Toshihide

  公开号：US20080138326A1

  公开（公告）日：2008-06-12

  Provided is a method for suppressing carcinogenesis, treating cancer, or mitigating adverse reactions of anticancer agents, with low prevalence of adverse reactions by administering an effective amount of a reduced coenzyme Q as an active ingredient. In the method, the reduced coenzyme Q can be administered in the form of pharmaceuticals, cosmeceutical, cosmetics, foods such as functional foods (supplements, health aid foods, nutritional supplementary foods, nutrient-fortified foods, nutrient-adjusted foods, health beverages, foods for specified health uses, foods with nutrient function claims), animal drugs, animal feeds, or animal foods.

  提供了一种通过给予有效量的还原型辅酶Q作为活性成分来抑制癌症发生、治疗癌症或减轻抗癌药物不良反应的方法，该方法具有低不良反应的发生率。在该方法中，还原型辅酶Q可以以制药品、化妆品、化妆品、食品（如功能性食品（补充剂、保健食品、营养补充食品、营养强化食品、营养调整食品、健康饮料、特定保健用途食品、带有营养功能声明的食品）、动物药品、动物饲料或动物食品的形式进行给予。