2-(2-nitrobenzyl)-malononitrile

• 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-(2-nitrobenzyl)-malononitrile
• 英文别名: 2-(2-nitrobenzyl)malononitrile；2-nitrobenzylmalononitrile；2-[(2-Nitrophenyl)methyl]propanedinitrile
• 化学式: C₁₀H₇N₃O₂
• 分子量: 201.184
• InChiKey: ZLVHMINCDJESEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  93.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-nitrobenzyl)-malononitrile 、 二苯基碘三氟甲烷磺酸盐 在 potassium tert-butylate 作用下， 以 二氯甲烷 为溶剂， 反应 1.16h， 以77%的产率得到2-(2-nitrobenzyl)-2-phenylmalononitrile
  参考文献：
  名称：

  使用二芳基碘鎓盐的叔丁醇钾介导的 2-取代丙二腈的芳基化

  摘要：

  开发了使用二芳基碘鎓盐直接芳基化 2-取代丙二腈而不涉及过渡金属催化剂。通过使用叔丁醇钾作为促进剂，合成了所需的 2-取代 α-芳基丙二腈衍生物，产率高达 55-96%。该合成方法为制备多种可用于农用化学品的2-取代芳基丙二腈提供了一种有效的方法。

  DOI：

  10.1055/s-0036-1589061
• 作为产物：
  描述：

  2-(2-nitrobenzylidene)malononitrile 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以5.10 g的产率得到2-(2-nitrobenzyl)-malononitrile
  参考文献：
  名称：

  单取代丙二腈：丙二腈与芳香醛的高效一锅还原烷基化反应

  摘要：

  已经开发了一种强大的新一锅法，用于丙二腈与芳香醛的还原烷基化。这种新工艺极大地提高了工艺的产率和效率，并扩大了芳香醛的范围。在缩合步骤的乙醇中加入水作为催化剂允许使用化学计量的丙二腈和醛。还原步骤用硼氢化钠快速有效地进行，通过过滤或萃取得到单取代的丙二腈。2-喹啉甲醛的产物迅速重排为新的中氮茚，而单取代衍生物的烷基化提供了不重排的不对称二取代丙二腈。

  DOI：

  10.1055/s-2007-990945

文献信息

• Base-Promoted Cascade Approach for the Preparation of Reduced Knoevenagel Adducts Using Hantzsch Esters as Reducing Agent in Water
  作者：Zhouyu Wang、Tao He、Ronghua Shi、Yimou Gong、Guangyou Jiang、Ming Liu、Shan Qian

  DOI：10.1055/s-0035-1562099

  日期：——

  condensation–reduction approach, which was carried out in water, has been reported. Using Hantzsch esters as reducing agent, under the promotion of base, a variety of reduced Knoevenagel adducts could be easily prepared by direct alkyl­ation of malononitrile, ethyl 2-cyanoacetate, and 2-(4-nitrophenyl)acetonitrile, respectively. Meanwhile, a gram-scale synthesis of the protocol was also realized with excellent

  已经报道了在水中进行的级联 Knoevenagel 缩合还原方法。以Hantzsch酯为还原剂，在碱的促进下，丙二腈、2-氰基乙酸乙酯和2-(4-硝基苯基)乙腈分别直接烷基化反应，可以很容易地制备出多种还原的Knoevenagel加合物。同时，该协议的克级合成也以优异的分离产率实现。
• Solvent-free mechanochemical and one-pot reductive benzylizations of malononitrile and 4-methylaniline using Hantzsch 1,4-dihydropyridine as the reductant
  作者：Ze Zhang、Jie Gao、Jing-Jing Xia、Guan-Wu Wang

  DOI：10.1039/b502662h

  日期：——

  Under mechanical milling conditions, direct reductive benzylizations of malononitrile and 4-methylaniline by aromatic aldehydes were achieved using a Hantzsch 1,4-dihydropyridine as the reductant.

  在机械研磨条件下，以 1,4-二氢吡啶为还原剂，实现了芳香醛对丙二腈和 4-甲基苯胺的直接还原苄化。
• Phosphine-Catalyzed [3+2] Annulation of Hepta-2,3,5-trienedioates with Alkenes for the Construction of Exocyclic Olefinic Cyclopentenes
  作者：Dongqiu Li、Xiaoqian Zhang、Wendan Han、Jiao Jiao、Yuhai Tang、Silong Xu

  DOI：10.1021/acs.joc.3c00550

  日期：2023.7.21

  employed as substrates to explore Lewis base-catalyzed annulation reactions. This leads to the discovery of a phosphine-catalyzed [3+2] annulation of 1 with electron-deficient alkenes for the construction of exocyclic olefinic cyclopentenes in good yields and moderate E:Z ratios under mild conditions. The annulation is believed to proceed in a tandem [3+2] cyclization and double bond migration in which the

  Hepta-2,3,5-三烯二酸酯1已被用作底物来探索路易斯碱催化的成环反应。这导致人们发现了膦催化的1与缺电子烯烃的 [3+2] 成环反应，用于在温和条件下以良好的产率和中等的E : Z比例构建外环烯属环戊烯。据信环化以串联[3+2]环化和双键迁移的方式进行，其中ε-酯对于这两个过程都至关重要。与之前的报告相比，该反应还表现出底物控制的不同反应性。
• The Synthesis of Some Derivatives Based on the 4-Benzyl-1H-pyrazole-3,5-diamine Core
  作者：Petr Cankař、Lukáš Jedinák、Vladimír Kryštof

  DOI：10.3987/com-10-12101

  日期：——

  The three-step synthesis of 4-benzyl-1H-pyrazole-3,5-diamines 2 from commercially available aldehydes 3 is given. The Knoevenagel condensation was utilized to assemble the initial carbon framework, resulting in the benzylidenemalononitriles 4 which were directly transformed by the reduction of the electron deficient C=C bond to benzylmalononitriles 5. Subsequent cycloaddition of hydrazine with 5 afforded the desired pyrazoles 2. Due to the high similarity with 4-arylazo-1H-pyrazole-3,5-diamines, the biological activities of the 4-benzyl-1H-pyrazole-3,5-diamines 2 were evaluated while focusing on the inhibition of cyclin-dependent kinases (CDKs), but no significant results were obtained.
• Study on comparison of reducing ability of three organic hydride compounds
  作者：Yi-Si Feng、Chun-Yan Yang、Qiang Huang、Hua-Jian Xu

  DOI：10.1016/j.tet.2012.04.047

  日期：2012.6

  Selective reduction of three kinds of substrates were studied to evaluate the reducing abilities of N,N-dimethyl-benzimidazolidine (DMBI), 2-phenylbenzimidazoline (PBI) and 2-phenylbenzothiazoline (PBT). As hydride donors, these three five-membered heterocyclic compounds performed different reducing abilities depending on the substrates. (C) 2012 Elsevier Ltd. All rights reserved.