2,3-dihydro-2,2,5,6-tetramethylpyrazine | 31839-61-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,3-dihydro-2,2,5,6-tetramethylpyrazine
• 英文别名: 3-hydro-2,2,5,6-tetramethylpyrazine；2,2,5,6-tetramethyl-2,3-dihydro-pyrazine；2,2,5,6-Tetramethyl-2,3-dihydropyrazine；3,3,5,6-tetramethyl-2H-pyrazine
• CAS: 31839-61-9
• 化学式: C₈H₁₄N₂
• 分子量: 138.213
• InChiKey: RINRSJBJOGCGBE-UHFFFAOYSA-N

物化性质

• 沸点：
  190.9±23.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-2,2,5,6-tetramethylpyrazine 以99%的产率得到(4aR*,9aS*)-2,2,4a,7,7,9a-hexamethyl-cyclohexano[1,2-e:4,5-e']-dipiperazin-6-ene
  参考文献：
  名称：

  Formation of Tricyclic Heterocycles from the Condensation Reaction of 1,2-Diamines with 1,2-Diketones.

  摘要：

  1，2-二胺与 1，2-二酮缩合产生了意想不到的三环杂环。其结构是通过单晶 X 射线分析确定的。

  DOI：

  10.1248/cpb.44.1977
• 作为产物：
  描述：

  2,3-丁二酮 、 1,2-二氨基-2-甲基丙烷 在 氢氧化钾 作用下， 以 乙醚 为溶剂， 以59.3%的产率得到2,3-dihydro-2,2,5,6-tetramethylpyrazine
  参考文献：
  名称：

  Dihydropyrazine Derivatives as a New Type of DNA Strand Breaking Agent.

  摘要：

  一些二氢吡嗪衍生物、2, 3-二氢-5, 6-二甲基吡嗪 (3)、2, 3-二氢-2, 5, 6-三甲基吡嗪 (4)、2, 3-二氢-2 的 DNA 链断裂活性, 2, 5, 6-四甲基吡嗪(5)，反式-2, 3-二甲基-5, 6, 7, 8, 9, 10-六氢喹喔啉(6)，其顺式化合物(7)以及6和的混合物使用质粒pBR322 ccc-DNA作为底物，通过琼脂糖凝胶电泳测试图7(8)。 Cu2+存在下DNA链断裂活性的顺序为(7)>(8)≥(5)>(2)>(6)>(4)≥(1)≥(3)。 2, 5-双(D-阿拉伯四羟基丁基)-2, 5-二氢吡嗪 (1) 和 2, 5-二氢-3, 6-二甲基吡嗪 (2) 已在之前的论文中根据 DNA 断裂活性进行了描述该活性被认为是由于二氢吡嗪骨架以及水溶液中形成的活性氧自由基所致。在二氢吡嗪骨架中引入甲基增强了二氢吡嗪衍生物的活性。讨论了二氢吡嗪衍生物造成 DNA 链断裂的可能化学基础，特别是在 Cu2+ 存在的情况下。

  DOI：

  10.1248/bpb.19.1261

文献信息

• Tetraazaindenes Derived from Dihydropyrazines with DNA Strand-Breaking Activity
  作者：Kazuhide Nakahara、Shinji Takechi、Koki Yamaguchi、Kazunobu Harano、Tadatoshi Yamaguchi

  DOI：10.1248/cpb.57.1371

  日期：——

  Dihydropyrazines (DHPs), which exhibit DNA strand-breaking activity and other biological activities associated with the generation of radical species, reacted with thiourea to give tetraazaindene (TAI) derivatives, despite thiourea is a well known radical scavenger. The structural determination of the TAIs was carried out and formation mechanism of TAI was investigated.

  尽管硫脲是众所周知的自由基清除剂，但二氢吡嗪（DHP）具有DNA链断裂活性和与自由基物质的产生相关的其他生物活性，与硫脲反应生成四氮杂茚（TAI）衍生物。进行了TAI的结构确定，并研究了TAI的形成机理。
• Process for the preparation of hydroxybenzylphosphonates
  申请人：Ciba-Geigy Corporation

  公开号：US05157141A1

  公开（公告）日：1992-10-20

  A process for the preparation of compounds of the general formula I ##STR1## in which R.sub.1 is hydrogen or methyl, R.sub.2 and R.sub.3 independently of one another are C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.8 cycloalkyl, phenyl, C.sub.7 -C.sub.9 phenylalkyl or halogen, R.sub.2 is additionally hydrogen and R.sub.7 and R.sub.8 independently of one another are C.sub.1 -C.sub.18 alkyl, phenyl or C.sub.7 -C.sub.18 alkylphenyl, which comprises reacting a phenol of the formula II ##STR2## in which R.sub.1 to R.sub.3 have the meaning described above, with formaldehyde or paraformaldehyde, an amine of the formula III NR.sub.4 R.sub.5 R.sub.6 III in which R.sub.4 is C.sub.1 -C.sub.4 alkyl and R.sub.5 and R.sub.6 independently of one another are hydrogen or C.sub.1 -C.sub.4 alkyl, and a phosphite of the formula IV ##STR3## in which R.sub.7 and R.sub.8 have the meaning described above and R.sub.9 has the meaning given for R.sub.7 and R.sub.8, at a temperature of 0.degree.-200.degree. C. Some compounds of the formula I are novel.

  一种制备一般式I化合物的方法，其中R1为氢或甲基，R2和R3独立地为C1-C18烷基，C5-C8环烷基，苯基，C7-C9苯基烷基或卤素，R2另外为氢，R7和R8独立地为C1-C18烷基，苯基或C7-C18烷基苯基。该方法包括将一种式II的酚与甲醛或多聚甲醛，式III的胺和式IV的亚磷酸酯反应，其中R1至R3的含义如上所述，R4为C1-C4烷基，R5和R6独立地为氢或C1-C4烷基，R7和R8的含义如上所述，R9的含义与R7和R8相同，反应温度为0℃-200℃。其中一些一般式I化合物是新的。
• Cyclohexyl substituted hydroxybenyzlphosphonates
  申请人：Ciba-Geigy Corporation

  公开号：US05258540A1

  公开（公告）日：1993-11-02

  Compounds of formula Ia ##STR1## in which R.sub.1 is hydrogen, R.sub.2 is methyl, tert-butyl or cyclohexyl, and R.sub.7 and R.sub.8 independently of one another are C.sub.1 -C.sub.18 alkyl, phenyl or C.sub.7 -C.sub.18 alkylphenyl are novel compounds having utility as stabilizers.

  式Ia的化合物：##STR1## 其中R.sub.1是氢，R.sub.2是甲基，叔丁基或环己基，R.sub.7和R.sub.8彼此独立地是C.sub.1-C.sub.18烷基，苯基或C.sub.7-C.sub.18烷基苯基，是一种具有稳定剂用途的新化合物。
• A novel monoalkylation of symmetrical α-diones
  作者：Damodaragounder Gopal、Durgesh V. Nadkarni、Lawrence M. Sayre

  DOI：10.1016/s0040-4039(98)00306-2

  日期：1998.4

  An efficient method has been developed for the synthesis of monoalkylated 1,2-diones by using steric approach control. The dihydropyrazine 2 prepared from 2,3-butanedione and 1,2-diamino-2-methylpropane is selectively deprotonated on the less hindered methyl group to give an anion which is alkylated with alkyl iodides and activated bromides. In situ hydrolysis of the alkylated dihydropyrazines gives monoalkylated diones 4 in good yield. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• New compounds derived from dihydropyrazines having DNA strand-breakage activity
  作者：Tadatoshi Yamaguchi、Masashi Eto、Kazunobu Harano、Nobuhiro Kashige、Kenji Watanabe、Shigeru Ito

  DOI：10.1016/s0040-4020(98)01079-5

  日期：1999.1

  Dihydropyrazine derivatives such as 2,3-dihydro-5,6-dimethylpyrazine (1), 2,3-dihydro-2,5,6-trimethylpyrazine (2) and 2,3-dihydro-2,2,5,6-teramethylpyrazine (3) were found to be transformed into (2R*, 3S*, 5R*)-1,2 ethylene-imino-1,7,10-triaza-2,3,6-trimethyl-3-hydroxy-spiro [4,5] decan-6-ene (4), the stereo-isomeric mixtures of 2,4aR*,7,9aS*-tetramethylcyclohexano [1,2-e: 4,5-e']-dipiperazin-6-ene (5) and (4aR*, 9aS*)-2,2,4a,7,7,9a-hexamethylcyclohexano [1,2-e: 4,5-e']-dipiperazin-6-ene (6), respectively. These dimerized compounds (4, 5 and 6), whose structures were determined by X-ray and nmr spectral analyses, showed almost the same DNA strand-breakage activity as their parent dihydropyrazines. The dimerization pathway is discussed on the basis of the PM3 calculation data. (C) 1998 Elsevier Science Ltd. All rights reserved.