2-amino-6-methyl-4,6-di(4-nitrophenyl)-2,4-cyclohexadiene-1,1,3-tricarbonitrile | 106000-63-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-amino-6-methyl-4,6-di(4-nitrophenyl)-2,4-cyclohexadiene-1,1,3-tricarbonitrile
• 英文别名: 5′-amino-3′-methyl-4,4″-dinitro-[1,1′:3′,1′-terphenyl]-4′,4′,6′(3′H)-tricarbonitrile；2-Amino-6-methyl-4,6-bis(4-nitrophenyl)cyclohexa-2,4-diene-1,1,3-tricarbonitrile；2-amino-6-methyl-4,6-bis(4-nitrophenyl)cyclohexa-2,4-diene-1,1,3-tricarbonitrile
• CAS: 106000-63-9
• 化学式: C₂₂H₁₄N₆O₄
• 分子量: 426.391
• InChiKey: CSBOBTBFWYNAAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  189
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-[1-(4-硝基苯基)亚乙基]丙二腈 在 乙酸铵 、 lithium dihydrogenphosphate 、 水 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 2-amino-6-methyl-4,6-di(4-nitrophenyl)-2,4-cyclohexadiene-1,1,3-tricarbonitrile
  参考文献：
  名称：

  New conditions for the synthesis of thiophenes via the Knoevenagel/Gewald reaction sequence. Application to the synthesis of a multitargeted kinase inhibitor

  摘要：

  Novel conditions have been developed for the preparation of substituted 2-aminothiophenes employing the Knoevenagel condensation followed by the Gewald reaction. The benefits of these conditions are their mildness, and the ease of product isolation. Thus, the Knoevenagel condensation is run in the presence of hexamethyldisilazane and acetic acid, which combine to perform the roles of desiccant, and catalyst. The Gewald reaction is performed with inorganic base in THF/water, which suppresses byproduct formation. This process has been employed in the total synthesis of a multitargeted kinase inhibitor. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.008

文献信息

• Syntheses of Donor–Acceptor-Functionalized Dihydroazulenes
  作者：Søren Lindbæk Broman、Martyn Jevric、Andrew D. Bond、Mogens Brøndsted Nielsen

  DOI：10.1021/jo4020326

  日期：2014.1.3

  properties relies on ready access to new derivatives via efficient synthetic protocols. The central DHA core is conveniently prepared in a four-step synthesis starting from acetophenone and tropylium substrates. Here, the outcome of this reaction as a function of the nature of the substituent group on the phenyl unit of acetophenone is investigated in detail. A wide variety of functional groups (nitro, cyano

  二氢氮杂烯（DHA）/乙烯基庚二烯（VHF）光电/热敏开关已被广泛用于分子电子学和高级材料中。先前已经发现两种异构体之间的转换很大程度上取决于供体和受体基团的存在。光学和开关特性的微调取决于通过有效的合成协议对新衍生物的便捷访问。中心DHA核心可方便地以四步合成的方式从苯乙酮和对苯二铵底物开始制备。在此，根据苯乙酮的苯基单元上的取代基的性质，对该反应的结果进行了详细研究。可以耐受多种官能团（硝基，氰基，卤素，烷基，酰胺基和硫醚），并且该路线为人们提供了更多选择的DHA衍生物（DHA的位置2）。通过区域选择性溴化-消除方案研究了这些化合物在七元环中随后进行官能化的能力，并在位置7引入了溴取代基。对卤代DHA进行了钯催化的氰化反应，Sonogashira，Cadiot-Chodkiewicz ，铃木联轴器以及后者的反应；通过改变钯催化剂开发了最佳条件。总的来说，我们的重点是减少完全不饱和的z烯
• Abramenko, Yu. T.; Ivashchenko, A. V.; Nogaeva, K. A., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, p. 230 - 235
  作者：Abramenko, Yu. T.、Ivashchenko, A. V.、Nogaeva, K. A.、Andronova, N. A.、Putsykina, E. B.

  DOI：——

  日期：——
• New conditions for the synthesis of thiophenes via the Knoevenagel/Gewald reaction sequence. Application to the synthesis of a multitargeted kinase inhibitor
  作者：David M. Barnes、Anthony R. Haight、Thomas Hameury、Maureen A. McLaughlin、Jianzhang Mei、Jason S. Tedrow、Joan Dalla Riva Toma

  DOI：10.1016/j.tet.2006.07.008

  日期：2006.12

  Novel conditions have been developed for the preparation of substituted 2-aminothiophenes employing the Knoevenagel condensation followed by the Gewald reaction. The benefits of these conditions are their mildness, and the ease of product isolation. Thus, the Knoevenagel condensation is run in the presence of hexamethyldisilazane and acetic acid, which combine to perform the roles of desiccant, and catalyst. The Gewald reaction is performed with inorganic base in THF/water, which suppresses byproduct formation. This process has been employed in the total synthesis of a multitargeted kinase inhibitor. (c) 2006 Elsevier Ltd. All rights reserved.