(+/-)-trans-2,3-dimethyl-5,6,7,8,9,10-hexahydroquinoxaline

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (+/-)-trans-2,3-dimethyl-5,6,7,8,9,10-hexahydroquinoxaline
• 英文别名: trans-2,3-dimethyl-4a,5,6,7,8,8a-hexahydroquinoxaline；trans-2,3-dimethyl-5,6,7,8,9,10-hexahydroquinoxaline；cis-2,3-dimethyl-5,6,7,8,9,10-hexahydroquinoxaline；(4aS,8aS)-2,3-dimethyl-4a,5,6,7,8,8a-hexahydroquinoxaline
• 化学式: C₁₀H₁₆N₂
• 分子量: 164.25
• InChiKey: TZNADPFQUNMWLB-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  Cis-1,2-diaminocyclohexane 、 (+/-)-trans-2,3-dimethyl-5,6,7,8,9,10-hexahydroquinoxaline 以61.7%的产率得到cis-2,3-trans-6,7-bis(tetramethylene)-cis-4a,8a-dimethyl-1,4,5,8-tetraazadecalin
  参考文献：
  名称：

  Products from a Novel Reaction of Di- hydropyrazines with Vichinaldiamines

  摘要：

  Dihydropyrazines such as 2,3-dihydro-5,6-dimethylpyrazine reacted with 1,2-diamines like ethylenediamine to form cis-tetraazadecalins (TADs) as crystalline products. The NMR spectra of the products in CDCl3 or CD3CN at -20 similar to -60 degrees C exhibited the signals due to TAD. However, the NMR spectra at room temperature showed that the TAD had dissociated into its parent materials. Seven TADs were obtained by only a mixing operation at a low temperature.

  DOI：

  10.3987/com-99-8678
• 作为产物：
  描述：

  2,3-丁二酮 、 trans-1,2-Diaminocyclohexane 以 水 为溶剂， 反应 0.5h， 以94%的产率得到(+/-)-trans-2,3-dimethyl-5,6,7,8,9,10-hexahydroquinoxaline
  参考文献：
  名称：

  喹喔啉和2,3-二氢吡嗪的绿色合成

  摘要：

  摘要 通过在水中简单地添加1,2-二胺和1,2-二羰基化合物，可以高收率获得喹喔啉和二氢吡嗪衍生物。在某些情况下，产物自发地从反应混合物中沉淀出来，使得有可能回收并再利用母液用于进一步的冷凝。非常温和的反应条件，高收率的产品以及不存在任何催化剂，使得该方法成为生产喹喔啉和二氢吡嗪的有效而绿色的途径。 通过在水中简单地添加1,2-二胺和1,2-二羰基化合物，可以高收率获得喹喔啉和二氢吡嗪衍生物。在某些情况下，产物自发地从反应混合物中沉淀出来，使得有可能回收并再利用母液用于进一步的冷凝。非常温和的反应条件，高收率的产品以及不存在任何催化剂，使得该方法成为生产喹喔啉和二氢吡嗪的有效而绿色的途径。

  DOI：

  10.1055/s-0033-1338441

文献信息

• Iridium-Catalyzed Condensation of Amines and Vicinal Diols to Substituted Piperazines
  作者：Linda L. R. Lorentz-Petersen、Lars Ulrik Nordstrøm、Robert Madsen

  DOI：10.1002/ejoc.201201099

  日期：2012.12

  A straightforward procedure is described for the synthesis of piperazines from amines and 1,2-diols. The heterocyclization is catalyzed by [Cp*IrCl2]2 and sodium hydrogen carbonate and can be achieved with either toluene or water as solvent. The transformation does not require any stoichiometric additives and only produces water as the byproduct. The reaction can be performed between a 1,2-diamine

  描述了从胺和 1,2-二醇合成哌嗪的简单程序。杂环化由 [Cp*IrCl2]2 和碳酸氢钠催化，可以用甲苯或水作为溶剂来实现。该转化不需要任何化学计量添加剂，只产生水作为副产品。该反应可以在 1,2-二胺和 1,2-二醇之间或通过伯烷基胺和 1,2-二醇之间的双缩合进行。哌嗪环上至少需要一个取代基才能以良好的收率实现环化。该机制被认为涉及 1,2-二醇脱氢为 α-羟基醛，后者与胺缩合形成 α-羟基亚胺。后者重排为相应的α-氨基羰基化合物，
• Dihydropyrazine Derivatives as a New Type of DNA Strand Breaking Agent.
  作者：Tadatoshi YAMAGUCHI、Nobuhiro KASHIGE、Noriko MISHIRO、Fumio MIAKE、Kenji WATANABE

  DOI：10.1248/bpb.19.1261

  日期：——

  The DNA strand-breaking activity of some dihydropyrazine derivatives, 2, 3-dihydro-5, 6-dimethylpyrazine (3), 2, 3-dihydro-2, 5, 6-trimethylpyrazine (4), 2, 3-dihydro-2, 2, 5, 6-tetramethylpyrazine (5), trans-2, 3-dimethyl-5, 6, 7, 8, 9, 10-hexahydroquinoxaline (6), its cis-compound (7) and the mixture of 6 and 7 (8) was tested by agarose gel electrophoresis using plasmide pBR322 ccc-DNA as a substrate. The order of DNA strand-breaking activity in the presence of Cu2+ was (7)>(8)≥(5)>(2)>(6)>(4)≥(1)≥(3). 2, 5-Bis(D-arabino-tetrahydroxybutyl)-2, 5-dihydropyrazine (1) and 2, 5-dihydro-3, 6-dimethylpyrazine (2) have already been described in terms of DNA breaking activity in a previous paper.The activity was suggested to be due to the dihydropyrazine skeleton, in addition to active oxygen radicals formed in an aqueous solutoin. The introduction of a methyl group to the dihydropyrazine skeleton enhanced the activities of dihydropyrazine derivatives. The possible chemical basis for DNA strand breakage by dihydropyrazine derivatives, especially in the presence of Cu2+, was discussed.

  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。
• A Diamine-Exchange Reaction of Dihydropyrazines
  作者：Tadatoshi Yamaguchi、Shigeru Ito、Yukiko Iwase、Kenji Watanabe、Kazunobu Harano

  DOI：10.3987/com-00-8932

  日期：——

  Dihydropyrazines reacted with 1,2-diamines to form tetraazadecalins as intermediates, and then the reaction proceeded forward to dissociate into alternate dihydropyrazine and diamine, or backward to dissociate into the starting materials in certain equilibrium. The product distribution is controlled by diamine-exchange equilibrium reaction. The various equilibrium reactions were analyzed by NMR spectroscopy.