2,3-cyano-5,6,7,8-tetrahydroquinoxaline | 52197-14-5

• 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: 2,3-cyano-5,6,7,8-tetrahydroquinoxaline
• 英文别名: 2,3-dicyano-5,6-cyclohexanopyrazine；5,6,7,8-tetrahydro-quinoxaline-2,3-dicarbonitrile；5,6,7,8-Tetrahydroquinoxaline-2,3-dicarbonitrile
• CAS: 52197-14-5
• 化学式: C₁₀H₈N₄
• 分子量: 184.2
• InChiKey: GTMRJHOFACALEU-UHFFFAOYSA-N

物化性质

• 熔点：
  137-139 °C
• 沸点：
  366.0±42.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  73.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-cyano-5,6,7,8-tetrahydroquinoxaline 在 magnesium n-propoxide 作用下， 以 丙醇 为溶剂， 反应 6.0h， 以60%的产率得到tetrakis(cyclohexylpyrazino)porphyrazinatomagnesium(II)
  参考文献：
  名称：

  The symmetrical porphyrazine with annulated six membered rings

  摘要：

  Tetrakis(cyclohexylpyrazino)porphyrazinato magnesium(II) with annulated six membered rings has been prepared by two different methods. In Method A: cyclotetramerization of 2,3-dicyano-5,6-cyclohexanopyrazine (1) in the presence of Mg(OPr)(2) in n-propanol afforded the tetrakis(cyclohexylpyrazino)porphyrazinato magnesium(II) (2). In Method B: selenodiazole rings on the periphery of tetrakis(selenodiazole)porphyrazinato magnesium(II) were opened by the action of H2S to yield the vicinal diamino functionalities. The ring closure of the vicinal diamino groups with 1,2-cyclohexanedione afforded the tetrakis(cyclohexylpyrazino) porphyrazinato magnesium(II) (2). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2009.12.012
• 作为产物：
  描述：

  氧化环己烯 、 二氨基马来腈 在 氢化铋 、 氧气 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二甲基亚砜 为溶剂， 100.0 ℃ 、101.32 kPa 条件下， 反应 3.5h， 以67%的产率得到2,3-cyano-5,6,7,8-tetrahydroquinoxaline
  参考文献：
  名称：

  Direct and catalytic synthesis of quinoxaline derivatives from epoxides and ene-1,2-diamines

  摘要：

  We describe here a new synthesis of quinoxaline derivatives by a Bi-catalyzed oxidative coupling of epoxides and a ene-1.2-diamines. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00715-3

文献信息

• A new facile, efficient synthesis and structure peculiarity of quinoxaline derivatives with two benzimidazole fragments
  作者：Vakhid A. Mamedov、Nataliya A. Zhukova、Victor V. Syakaev、Aidar T. Gubaidullin、Tat'yana N. Beschastnova、Dil'bar I. Adgamova、Aida I. Samigullina、Shamil K. Latypov

  DOI：10.1016/j.tet.2012.10.045

  日期：2013.1

  A highly efficient and versatile method for the synthesis of quinoxaline derivatives with two benzimidazole fragments have been developed on the basis of the ring contraction of 3-(benzimidazo-2-yl)quinoxalin-2(1H)-one with 1,2-diaminobenzene and its various types of substituted and condensed derivatives. Owing to the inter- and intramolecular processes, involving self association, proton exchange

  基于3-（苯并咪唑-2-基）喹喔啉-2（1 H）-与1,2-的环收缩，已开发出一种高效且通用的具有两个苯并咪唑片段的喹喔啉衍生物的合成方法。二氨基苯及其各种类型的取代和稠合衍生物。由于分子间和分子内过程，涉及桥联和相邻碳原子的大多数双-苯并咪唑基喹喔啉信号的几种形式之间的自缔合，质子交换，构象和/或互变异构交换，且NMR光谱中的苯并咪唑片段变宽。苯并咪唑片段与分子的喹喔啉核心之间的共轭作用比喹喔啉衍生物（10c）与其噻二唑[ f ]-（17）和吡咯并[ a ]-（19）环化了衍生物，导致整个分子的平面度更大。
• Ried, Walter; Lee, Chiu-Huei; Bats, Jan W., Liebigs Annalen der Chemie, 1989, p. 497 - 500
  作者：Ried, Walter、Lee, Chiu-Huei、Bats, Jan W.

  DOI：——

  日期：——
• Direct and catalytic synthesis of quinoxaline derivatives from epoxides and ene-1,2-diamines
  作者：Sylvain Antoniotti、Elisabet Duñach

  DOI：10.1016/s0040-4039(02)00715-3

  日期：2002.5

  We describe here a new synthesis of quinoxaline derivatives by a Bi-catalyzed oxidative coupling of epoxides and a ene-1.2-diamines. (C) 2002 Elsevier Science Ltd. All rights reserved.
• The symmetrical porphyrazine with annulated six membered rings
  作者：Hilal Onay、Burak Esat、Ramazan Öztürk

  DOI：10.1016/j.poly.2009.12.012

  日期：2010.3

  Tetrakis(cyclohexylpyrazino)porphyrazinato magnesium(II) with annulated six membered rings has been prepared by two different methods. In Method A: cyclotetramerization of 2,3-dicyano-5,6-cyclohexanopyrazine (1) in the presence of Mg(OPr)(2) in n-propanol afforded the tetrakis(cyclohexylpyrazino)porphyrazinato magnesium(II) (2). In Method B: selenodiazole rings on the periphery of tetrakis(selenodiazole)porphyrazinato magnesium(II) were opened by the action of H2S to yield the vicinal diamino functionalities. The ring closure of the vicinal diamino groups with 1,2-cyclohexanedione afforded the tetrakis(cyclohexylpyrazino) porphyrazinato magnesium(II) (2). (C) 2009 Elsevier Ltd. All rights reserved.