3-amino-2-nitro-1-phenyl-9,10-dihydrophenanthrene-4-carbonitrile | 119452-32-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3-amino-2-nitro-1-phenyl-9,10-dihydrophenanthrene-4-carbonitrile
• CAS: 119452-32-3
• 化学式: C₂₁H₁₅N₃O₂
• 分子量: 341.369
• InChiKey: WMBKBLOYBVPMEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  95.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-[2-(1-phenyl-2-nitroethyl)-3,4-dihydro-2H-naphthalen-1-ylidene]malononitrile 在 sodium ethanolate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 3-amino-2-nitro-1-phenyl-9,10-dihydrophenanthrene-4-carbonitrile
  参考文献：
  名称：

  乙烯基丙二腈与硝基烯烃一键串联反应合成多取代苯的有效方法

  摘要：

  一键合成多取代苯衍生物是通过乙烯基丙烯腈和硝基烯烃的乙烯基乙烯基加成反应（作为关键步骤）和顺序串联反应实现的。可以以令人满意的产率获得一系列复杂的芳基化合物，例如联苯和三联苯。

  DOI：

  10.1021/jo070766i

文献信息

• Cu(OTf)2/Et3N-promoted cyclocondensation of activated α-methylene alkenes and nitroolefins: a novel one-pot synthesis of polysubstituted benzenes
  作者：Weike Su、Kai Ding、Zhiwei Chen

  DOI：10.1016/j.tetlet.2008.11.081

  日期：2009.2

  A simple and efficient one-pot synthesis of polyfunctionalized benzenes has been developed via cyclocondensation of activated α-methylene alkenes such as vinyl malononitriles and ethyl vinyl cyanoacetates with nitroolefins using Cu(OTf)2/Et3N as a novel catalytic system.

  通过使用Cu（OTf）2 / Et 3 N作为新型催化体系，将活化的α-亚甲基烯烃（如乙烯基丙二腈和乙基乙烯基氰基乙酸酯）与硝基烯烃进行环缩反应，已开发出一种简单高效的一锅多官能苯合成方法。
• Basic Ionic Liquid as Catalyst for the Efficient and Green Synthesis of 2-Amino-3-nitrobenzonitriles in Ethanol
  作者：Zhiwei Chen、Kai Ding、Weike Su

  DOI：10.1080/00397911.2010.486503

  日期：2011.4.19

  [image omitted] A basic ionic liquid, [BmIm]OH was used as catalyst in the cyclocondensation of various kinds of vinylmalononitriles with nitroolefins in ethanol at reflux. A series of 2-amino-3-nitrobenzonitriles were obtained in reasonable yields. The straightforward and green protocol was found to be fairly efficient, and the catalyst could be recycled and reused in subsequent reactions with consistent activity. The mechanism of the reaction was discussed.
• BOGDANOWICZ-SZWED, KRYSTYNA;LIPOWSKA, MALGORZATA, CHEM. SCR., 28,(1988) N 3, C. 319-322
  作者：BOGDANOWICZ-SZWED, KRYSTYNA、LIPOWSKA, MALGORZATA

  DOI：——

  日期：——
• Efficient Method for the Synthesis of Polysubstituted Benzenes by One-Pot Tandem Reaction of Vinyl Malononitriles with Nitroolefins
  作者：Dong Xue、Jie Li、Zun-Ting Zhang、Jin-Gen Deng

  DOI：10.1021/jo070766i

  日期：2007.7.1

  The one-pot synthesis of polysubstituted benzene derivatives was achieved via vinylogous Michael addition of vinyl malononitriles and nitroolefins as the key step and a sequential tandem reaction. A series of complex aryl compounds such as biphenyls and terphenyls can be obtained with satisfactory yields.

  一键合成多取代苯衍生物是通过乙烯基丙烯腈和硝基烯烃的乙烯基乙烯基加成反应（作为关键步骤）和顺序串联反应实现的。可以以令人满意的产率获得一系列复杂的芳基化合物，例如联苯和三联苯。