2(-2-amino-6-bromo-3-cyano-4H-chromen-4-yl)malononitrile | 675573-59-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2(-2-amino-6-bromo-3-cyano-4H-chromen-4-yl)malononitrile
• 英文别名: Propanedinitrile, (2-amino-6-bromo-3-cyano-4H-1-benzopyran-4-yl)-；2-(2-amino-6-bromo-3-cyano-4H-chromen-4-yl)propanedinitrile
• CAS: 675573-59-8
• 化学式: C₁₃H₇BrN₄O
• 分子量: 315.129
• InChiKey: LXQDTMNJKPKLSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  丙二腈 、 2(-2-amino-6-bromo-3-cyano-4H-chromen-4-yl)malononitrile 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 (2,4-diamino-7-bromo-3-cyano-5H-chromeno[2,3-b]pyridin-5-yl)malononitrile
  参考文献：
  名称：

  Aminocyanopyridine inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)

  摘要：

  A class of inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2) was discovered. These compounds have demonstrated activity against the enzyme with IC50 values as low as 130 nM and suppress the expression of TNFα in U937 cells. These represent the first small molecule inhibitors of MK-2 to be reported. © 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.067
• 作为产物：
  描述：

  5-溴水杨醛 以 水 为溶剂， 反应 0.5h， 生成 2(-2-amino-6-bromo-3-cyano-4H-chromen-4-yl)malononitrile
  参考文献：
  名称：

  Synthesis of 4 H ‐chromene‐isoxazole hybrids via ortho ‐hydroxy directing cyclization of isoxazole‐styrenes and Michael addition of imino‐chromenes in aqueous medium

  摘要：

  AbstractA green, efficient, and one‐pot method synthesis of functionalized 4H‐chromene‐isoxazole hybrids is reported via o‐hydroxy group directing cyclization of isoxazole‐styrenes and Michael addition of 3,5‐dimethyl‐4‐nitroisoxazole on 2‐imino‐2H‐chromene‐3‐carbonitrile (independent methods). The developed methodology was further extended for nitromethane, malononitrile, and alkylcyanoacetates as Michael donors.

  DOI：

  10.1002/jhet.4251

文献信息

• First report of the application of simple molecular complexes as organo-catalysts for Knoevenagel condensation
  作者：Sumit Kumar Panja、Nidhi Dwivedi、Satyen Saha

  DOI：10.1039/c5ra09036a

  日期：——

  Knoevenagel condensation is used to synthesize a series of important cyano group containing synthetic precursors for synthesis of biologically active molecules at RT using a minimum amount of catalyst (∼5 mol%) without the need for chromatographic separation techniques. Detailed mechanistic studies and substituent effects of aromatic aldehydes on the reaction have been investigated. In addition, biologically

  为了非常有效的Knoevenagel缩合反应，首次设计，合成了一系列分子配合物并将其用作有机催化剂。分子配合物是热稳定的，易于回收，并且制备成本低。酸性质子在Knoevenagel缩合的分子复合物中的作用已被确定为关键因素，可帮助我们提供有关反应途径的有用信息。催化剂的酸性质子增强了醛的亲电性，并加速了室温（RT）下反应的脱水过程。环保，用于Knoevenagel缩合反应的绿色合成方案用于合成一系列重要的含氰基的合成前体，用于在室温下使用最少量的催化剂（〜5 mol％）合成生物活性分子，而无需色谱分离技术。已经研究了详细的机理研究和芳族醛对反应的取代作用。此外，具有生物活性的2-氨基-4还可以通过水杨醛与活性亚甲基化合物的Knoevenagel缩合反应，然后进行分子内环化（通过Michael加成反应），在RT较短的反应时间内获得更高的收率，而无需色谱分离，从而合成了H-色烯衍生物。
• The Condensation of Salicylaldehydes and Malononitrile Revisited:  Synthesis of New Dimeric Chromene Derivatives
  作者：Marta Costa、Filipe Areias、Luís Abrunhosa、Armando Venâncio、Fernanda Proença

  DOI：10.1021/jo702552f

  日期：2008.3.1

  The reaction of salicylic aldehydes with malononitrile was reinvestigated, and the reaction pathway was followed by 1H NMR spectroscopy. A delicate control of the experimental conditions allowed the synthesis of 2-imino-2H-chromene-3-carbonitriles 1, (2-amino-3-cyano-4H-chromen-4-yl)malononitriles 2, 4-amino-5-imino-2,7-dimethoxy-5H-chromeno[3,4-c]pyridine-1-carbonitrile 12, and (4,5-diamino-1-cyano-1

  重新研究了水杨醛与丙二腈的反应，并通过1 H NMR光谱追踪了反应路径。的实验条件微妙控制允许的2-亚氨基-2-合成ħ色烯-3-腈1，（2-氨基-3-氰基-4- ħ -苯并吡喃-4-基）丙二腈2，4-氨基5-亚氨基-2,7-二甲氧基-5- ħ -chromeno [3,4 ç ]吡啶-1-甲腈12，和（4,5-二氨基-1-氰基1,10b二氢-2 ħ -chromeno [3,4- c ]吡啶-2-亚基）丙二腈13。两个新颖的2-亚氨基二烯二聚体，分别具有结构8和9，被隔离和充分表征。化合物8a对曲霉属的活性。生长和曲霉毒素A的产生进行了评估。生物测定的结果表明，以2mM的浓度施用的化合物8a完全抑制了所测试的真菌的生长。赭曲霉毒素A的生产由曲霉alliaceus减少了约93％的与该化合物的200μM溶液。观察到对类似结构8b的中等抑制作用，并且未发现对用作二聚体8的合成前体的化合物2和1有抑制作用。
• Visible light induced, catalyst free, convenient synthesis of chromene nucleus and its derivatives using water–ethanol mixture as a solvent
  作者：Snehlata Yadav、Madhulika Srivastava、Pratibha Rai、Jaya Singh、Kamla Prasad Tiwari、Jagdamba Singh

  DOI：10.1039/c5nj00002e

  日期：——

  Eco-friendly, one pot synthesis of chromene and pyridine nucleus initiated by visible light.

  环保的，一锅法合成由可见光引发的咔啉和吡啶核。
• Electrocatalytic chain transformation of salicylaldehyde and CH acids into substituted 4H-chromenes
  作者：S. K. Feducovich、M. N. Elinson、A. S. Dorofeev、S. V. Gorbunov、R. F. Nasybullin、N. O. Stepanov、G. I. Nikishin

  DOI：10.1007/s11172-008-0093-9

  日期：2008.3

  Electrochemically initiated catalytic chain transformation of salicylaldehydes and CH acids containing the cyano group in an ethanolic solution in an undivided cell produced substituted 4H-chromenes in 85–95% yields.

  电化学引发的水杨醛和含有氰基的 CH 酸在乙醇溶液中的催化链转化在未分开的电池中产生了取代的 4H-色烯，产率为 85-95%。
• Diethylamine: A smart organocatalyst in eco-safe and diastereoselective synthesis of medicinally privileged 2-amino-4H-chromenes at ambient temperature
  作者：Makarand A. Kulkarni、Kapil S. Pandit、Uday V. Desai、Uday P. Lad、Prakash P. Wadgaonkar

  DOI：10.1016/j.crci.2013.02.016

  日期：2013.8

  Résumé Diethylamine has been demonstrated to be an efficient organocatalyst in the diastereoselective synthesis of Bcl-2 protein antagonist (HA-14-1) and of its structural analogues by one-pot condensation between salicylaldehyde and three different C–H acids, viz. ethyl cyanoacetate, phenylsulfonyl acetonitrile, and malononitrile. Easy commercial availability of the catalyst at extremely low cost and avoidance of conventional work-up as well as purification procedures qualifies this scalable protocol for a “near-ideal synthesis”. Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.docx

  摘要 二乙胺已被证明是一个高效的有机催化剂，能够以一次性缩合法选择性合成Bcl-2蛋白拮抗剂（HA-14-1）及其结构类似物，该方法通过水杨醛与三种不同的C–H酸（即乙基氰乙酸酯、苯基磺酰乙腈和丙二腈）反应实现。该催化剂在商业上的易得性和极低的成本，以及避免传统的后处理和纯化程序，使这一可扩展的方案符合“近乎理想合成”的标准。 补充材料： 本文的补充材料作为单独文件提供： mmc1.docx