2-(4-Pyridin-2-yl-benzylidene)-malononitrile | 771566-44-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(4-Pyridin-2-yl-benzylidene)-malononitrile
• 英文别名: 2-[(4-Pyridin-2-ylphenyl)methylidene]propanedinitrile；2-[(4-pyridin-2-ylphenyl)methylidene]propanedinitrile
• CAS: 771566-44-0
• 化学式: C₁₅H₉N₃
• 分子量: 231.257
• InChiKey: AVKAMBSAVCVNCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-Pyridin-2-yl-benzylidene)-malononitrile 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以0.460 g的产率得到4-(2-pyridyl)benzylmalononitrile
  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
• 作为产物：
  描述：

  2-溴吡啶 在 四氢吡咯 、 potassium phosphate monohydrate 、 palladium diacetate 作用下， 以 水 、 异丙醇 为溶剂， 反应 4.0h， 生成 2-(4-Pyridin-2-yl-benzylidene)-malononitrile
  参考文献：
  名称：

  Synthesis, thermal and optical properties of a novel bis(2-(4-dicyanovinylphenyl)pyridinato-N,C2)iridium(acetylacetonate)

  摘要：

  Bis(2-(4-formylphenyl) pyridinato-N, C2) iridium(acetylacetonate) (5) was subjected to a Knoevenagel reaction with malononitrile in dichloromethane in the presence of catalytic amount of pyrrolidine. This gave successfully a novel bis(2-(4-dicyanovinylphenyl) pyridinato-N, C2) iridium(acetylacetonate) (6) in good yield (83%). Complex 6 was fully chracterised by H-1, C-13 NMR, FT-IR, elemental analysis. Complex 6 showed a strong ligand centred (LC) absorption band at 355 nm (epsilon 56490 L mol (1) cm (1)) and weak metal-to-ligand charge transfer (MLCT) bands at 445 (epsilon 4154 L mol (1) cm (1)) and 535 nm (epsilon 2606 L mol (1) cm (1)). Complex 6 loses its acac moiety between 248 and 336 Alpha degrees C (under N-2 atmosphere) and emits a red light at 695 nm with a large Stokes shift (160 nm). (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2015.10.028

文献信息

• Tris(hydroxymethyl)aminomethane as an efficient organobase catalyst for the synthesis of β-phosphonomalonates
  作者：Reddi Mohan Naidu Kalla、Il Kim

  DOI：10.1016/j.tetlet.2016.12.035

  日期：2017.2

  Tris(hydroxymethyl)aminomethane (THAM) is a highly efficient and recyclable organobase catalyst for the nucleophilic phosphonylation of benzylidene malononitrile under solvent-free conditions. This new catalytic methodology is applicable without a solvent, eco-friendly, economically viable, avoids conventional isolation procedures, and has a facile work-up procedure and wide scope. THAM is an inexpensive

  三（羟甲基）氨基甲烷（THAM）是高效和可回收的有机碱催化剂，可在无溶剂条件下进行亚苄基丙二腈的亲核膦酰化反应。这种新的催化方法学适用于无溶剂，生态友好，经济可行，避免常规分离程序，后处理程序简便，适用范围广的情况。THAM是一种廉价的，可商购的，无毒且可生物降解的新型有机催化剂。此外，它最多可以重复使用五个循环而不会降低催化活性，并且不需要色谱分离即可获得所需的产物。
• Monosubstituted Malononitriles: Efficient One-Pot Reductive Alkylations of Malononitrile with Aromatic Aldehydes
  作者：Robert Sammelson、Fariba Tayyari、Dwight Wood、Phillip Fanwick

  DOI：10.1055/s-2007-990945

  日期：2008.1

  been developed for the reductive alkylation of malononitrile with aromatic aldehydes. This new procedure has vastly improved the yield and efficiency of the process, and increased the scope of the aromatic aldehydes. Incorporating water as the catalyst in ethanol for the condensation step allows stoichiometric amounts of malononitrile and aldehyde to be employed. The reduction step takes place quickly

  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。
• Synthesis, thermal and optical properties of a novel bis(2-(4-dicyanovinylphenyl)pyridinato-N,C2)iridium(acetylacetonate)
  作者：Nuray Altınölçek、Mustafa Tavasli、Murat Aydemir、Bahattin Abay、Andrew P. Monkman

  DOI：10.1016/j.ica.2015.10.028

  日期：2016.1

  Bis(2-(4-formylphenyl) pyridinato-N, C2) iridium(acetylacetonate) (5) was subjected to a Knoevenagel reaction with malononitrile in dichloromethane in the presence of catalytic amount of pyrrolidine. This gave successfully a novel bis(2-(4-dicyanovinylphenyl) pyridinato-N, C2) iridium(acetylacetonate) (6) in good yield (83%). Complex 6 was fully chracterised by H-1, C-13 NMR, FT-IR, elemental analysis. Complex 6 showed a strong ligand centred (LC) absorption band at 355 nm (epsilon 56490 L mol (1) cm (1)) and weak metal-to-ligand charge transfer (MLCT) bands at 445 (epsilon 4154 L mol (1) cm (1)) and 535 nm (epsilon 2606 L mol (1) cm (1)). Complex 6 loses its acac moiety between 248 and 336 Alpha degrees C (under N-2 atmosphere) and emits a red light at 695 nm with a large Stokes shift (160 nm). (C) 2015 Elsevier B.V. All rights reserved.