2‑amino‑3‑cyano‑7-hydroxy‑4‑(2‑fluorophenyl)‑4H‑chromene | 111861-26-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 2‑amino‑3‑cyano‑7-hydroxy‑4‑(2‑fluorophenyl)‑4H‑chromene
• 英文别名: 2-amino-3-cyano-4-(2-fluorophenyl)-7-hydroxy-4H-chromene；2-amino-3-cyano-7-hydroxy-4-(2-fluorophenyl)-4H-chromene；2-Amino-4-(2-fluorophenyl)-7-hydroxy-4H-chromene-3-carbonitrile
• CAS: 111861-26-8
• 化学式: C₁₆H₁₁FN₂O₂
• 分子量: 282.274
• InChiKey: VFLUQOJSEVHLBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  79.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-[(2-氟苯基)亚甲基]丙二腈 、 间苯二酚 在 吗啉 作用下， 以 丙酮 为溶剂， 反应 0.08h， 以85%的产率得到2‑amino‑3‑cyano‑7-hydroxy‑4‑(2‑fluorophenyl)‑4H‑chromene
  参考文献：
  名称：

  Klokol, G.V.; Sharanina, L.G.; Nesterov, V.N., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, p. 369 - 377

  摘要：

  DOI：

文献信息

• An expeditious synthesis of novel pyranopyridine derivatives involving chromenes under controlled microwave irradiation
  作者：Dushyant Singh Raghuvanshi、Krishna Nand Singh

  DOI：10.3998/ark.5550190.0011.a25

  日期：——

  An efficient synthesis of novel pyrano[2,3-b]pyridine derivatives has been achieved by the cyclocondensation of 2-amino-3-cyano-4H-chromenes and cyclohexanone in the presence of aluminium chloride under controlled microwave irradiation. The experimental conditions have been thoroughly optimized and established, allowing significant rate enhancements and excellent yields. The starting 4H-chromenes were

  2-氨基-3-氰基-4H-色烯和环己酮在氯化铝存在下，在受控的微波辐射下进行环缩合反应，实现了新型吡喃并[2,3-b]吡啶衍生物的有效合成。实验条件已经过彻底优化和建立，可以显着提高速率和优异的产量。使用一锅 DBU 催化的微波诱导间苯二酚、丙二腈和芳香醛的多组分缩合获得起始 4H-色烯。
• A facile and efficient synthesis of 2-amino-3-cyano-4H-chromenes and tetrahydrobenzo[b]pyrans using 2,2,2-trifluoroethanol as a metal-free and reusable medium
  作者：Samad Khaksar、Ahmad Rouhollahpour、Saeed Mohammadzadeh Talesh

  DOI：10.1016/j.jfluchem.2012.05.014

  日期：2012.9

  A highly efficient one-pot three-component regioselective synthesis of 2-amino-3-cyano-4H-chromene and tetrahydrobenzo[b]pyran derivatives has been developed by annulation of aldehydes, malononitrile, and resorcinol or dimedone under reflux conditions in 2,2,2-trifluoroethanol without the use of a catalyst or any other additive.

  通过在回流条件下2醛，丙二腈和间苯二酚或二甲酮的环化反应，已经开发出了一种高效的一锅三组分区域选择性合成2-氨基-3-氰基-4 H-色烯和四氢苯并[ b ]吡喃衍生物的方法。 ，2,2-三氟乙醇，不使用催化剂或任何其他添加剂。
• Green protocol for synthesis of MgFe2O4 nanoparticles and study of their activity as an efficient catalyst for the synthesis of chromene and pyran derivatives under ultrasound irradiation
  作者：Bahar Eshtehardian、Morteza Rouhani、Zohreh Mirjafary

  DOI：10.1007/s13738-019-01783-3

  日期：2020.2

  procedure to synthesize 2-amino-7-hydroxy-4H-chromene and tetrahydrobenzo[b]pyran derivatives was established through the chemical reaction between different aldehydes, malononitrile and resorcinol (or dimedone) in the presence of MgFe2O4 nanoparticles as a beneficial catalyst in ethanol as solvent under ultrasound irradiation. Moreover, the synthesized MgFe2O4 nanoparticles were easily recovered by an

  在这项研究中，MgFe 2 O 4纳米颗粒是通过绿色和简单的方法合成的。然后在MgFe 2 O 4存在下，通过不同醛，丙二腈和间苯二酚（或二甲酮）之间的化学反应，建立了合成2-氨基-7-羟基-4 H-色烯和四氢苯并[ b ]吡喃衍生物的有效方法。超声辐照下，纳米颗粒作为有益的催化剂，以乙醇为溶剂。此外，合成的MgFe 2 O 4纳米粒子很容易通过外部磁体回收，并重复使用了四次，而不会显着降低其催化活性。简单，快速，有效，生态友好以及快速纯化方法以及高产物收率是本化学反应的一些优点。
• Saccharose as a new, natural, and highly efficient catalyst for the one-pot synthesis of 4,5-dihydropyrano[3,2-c]chromenes, 2-amino-3-cyano-4H-chromenes, 1,8-dioxodecahydroacridine, and 2-substituted benzimidazole derivatives
  作者：Malek Taher Maghsoodlou、Nourallah Hazeri、Mojtaba Lashkari、Fereshteh Nejad Shahrokhabadi、Behzad Naghshbandi、Mohammad Saeed Kazemi-doost、Mahnaz Rashidi、Fatemeh Mir、Mehrnoosh Kangani、Sajjad Salahi

  DOI：10.1007/s11164-014-1793-4

  日期：2015.10

  Saccharose was applied as a green and natural catalyst for the one-pot, three-component condensation between aromatic aldehydes, malononitrile, and resorcinol, or 4-hydroxycoumarine to afford the corresponding pyran-annulated heterocyclic systems. This green methodology offers several advantages such as the use of a non-hazardous catalyst, easy access, clean work-up, excellent yields, short reaction time, and environmentally mild conditions. In addition, 1,8-dioxodecahydroacridine and 2-substituted benzimidazole derivatives have been synthesized from commercially available starting materials, arylaldehydes, dimedone, amines, or ammonium acetate and o-phenylenediamine using the mentioned catalyst.

  蔗糖被用作绿色和天然催化剂，进行芳香醛、马来腈和儿茶酚或4-羟基香豆素之间的一锅三组分缩合反应，生成相应的吡喃缩合杂环体系。这种绿色方法具有多个优点，如使用无害催化剂、易于获得、清洁的后处理、优良的产率、短的反应时间以及环保的温和条件。此外，1,8-二氧代十氢吡啶和2-取代苯并咪唑衍生物是通过上述催化剂从商业可获得的起始材料（芳香醛、二酮、胺或醋酸铵和邻苯二胺）合成的。
• Magnetic Fe₃O₄ Nanoparticles as Efficient and Reusable Catalyst for the Green Synthesis of 2-Amino-4<i>H</i>-chromene in Aqueous Media
  作者：Javad Safari、Zohre Zarnegar、Marzieh Heydarian

  DOI：10.1246/bcsj.20120209

  日期：2012.12.15

  A simple and efficient protocol for one-pot three-component coupling of aldehyde, malononitrile, and resorcinol in water using magnetically recoverable Fe3O4 nanoparticles at room temperature is reported. The high yields of products and short reaction time were attributed to the nanosize of about 18 nm in which the catalyst could act as a nanoreactor. This methodology is found to be fairly general and catalyst is easily separated by magnetic devices and can be reused without any apparent loss of activity for the reaction.

  报告了一种在室温下利用磁性可回收 Fe3O4 纳米粒子在水中实现醛、丙二腈和间苯二酚三组分一锅偶联的简单而高效的方案。由于催化剂的纳米尺寸约为 18 纳米，可用作纳米反应器，因此产物产量高，反应时间短。研究发现，这种方法相当通用，催化剂很容易通过磁性装置分离出来，而且可以重复使用，不会明显丧失反应活性。