2-amino-4-(furan-2-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile | 85459-85-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-4-(furan-2-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
• 英文别名: 2-amino-4-(furan-2-yl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile；2-amino-3-cyano-4-(furan-2-yl)-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran；2-amino-7,7-dimethyl-5-oxo-4-(furan-2-yl)-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；2-amino-4-(2-furyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；2-amino-4-(furan-2-yl)-7,7-dimethyl-5-oxo-6,8-dihydro-4H-chromene-3-carbonitrile
• CAS: 85459-85-4
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: BCWJDLZORIVLIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-4-(furan-2-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 在 水 、 对甲苯磺酸 作用下， 反应 7.0h， 以79%的产率得到4-furan-2-yl-7,7-dimethyl-2,5-dioxo-1,2,3,4,5,6,7,8-octahydro-quinoline-3-carbonitrile
  参考文献：
  名称：

  Nano crystalline ZnO catalyzed one pot multicomponent reaction for an easy access of fully decorated 4H-pyran scaffolds and its rearrangement to 2-pyridone nucleus in aqueous media

  摘要：

  A green and highly efficient protocol has been developed for the synthesis of 4H-pyran scaffolds installing a one-pot three-component coupling reaction of an aldehyde, malononitrile, and a 1,3-diketo compound using nano structured ZnO as the catalyst in aqueous alcoholic medium. A greener method to synthesize 3,4-dihydropyridin-2-one has also been developed by rearranging 4H-pyran derivatives in aqueous medium applying p-TSOH as the right catalyst source. A wide spectrum of functional groups was tolerated in both the developed synthetic protocols with good to excellent yield of the targeted molecules. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.086
• 作为产物：
  描述：

  (2-呋喃亚甲基)丙二腈 、 5,5-二甲基-1,3-环己二酮 在 吗啉 作用下， 以 乙醇 为溶剂， 以74%的产率得到2-amino-4-(furan-2-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  5-oxo-5,6,7,8-Tetrahydro-4H-Chromene 衍生物的合成及杀软体动物活性

  摘要：

  糠基丙二腈和噻吩基丙二腈用 1,3-环己二酮处理得到 2-氨基-4-杂芳基-5-氧代-5,6,7,8-四氢-4H-色烯-3-甲腈衍生物。研究了这些化合物的杀软体动物活性。

  DOI：

  10.1002/ardp.200400881

文献信息

• Synthesis of functionalized chromene and spirochromenes using l -proline-melamine as highly efficient and recyclable homogeneous catalyst at room temperature
  作者：Sakkani Nagaraju、Banoth Paplal、Kota Sathish、Santanab Giri、Dhurke Kashinath

  DOI：10.1016/j.tetlet.2017.09.060

  日期：2017.11

  commercially cheap l-proline and melamine for the synthesis of chromenes and spirochromenes (spirooxindoles) via multicomponent reactions at room temperature. Systematic studies were conducted in order to achieve desired reactivity and recyclability of the catalyst using various α-amino acids and aromatic amines as donor-acceptor pairs. Among the screened combinations, l-proline and melamine (3:1 ratio;

  使用便宜的1-脯氨酸和三聚氰胺开发了一种有效且可循环使用的均相催化剂，用于在室温下通过多组分反应合成色烯和螺环色酮（螺并辛多烯）。为了使用各种α-氨基酸和芳族胺作为供体-受体对，进行系统研究以实现所需的反应性和催化剂的可回收性。在筛选的组合中，l脯氨酸和三聚氰胺（3：1的比例；占总重量的3 mol％）被认为是最佳的催化剂，可以在室温下非常短的时间内（1-15分钟）以优异的产率（高达99％）提供所需的产品在DMSO中作为溶剂。通过添加EtOAc来回收催化剂，并且在不损失催化活性的情况下重复使用多达5个循环。
• One-pot synthesis of 2-amino-3-cyano-4<i>H</i>-pyrans and pyran-annulated heterocycles using sodium citrate as an organo-salt based catalyst in aqueous ethanol
  作者：Aiborlang Thongni、Pynskhemborlang T. Phanrang、Arup Dutta、Rishanlang Nongkhlaw

  DOI：10.1080/00397911.2021.1998535

  日期：2022.1.2

  shorter reaction time, utilization of eco-friendly solvents, operational simplicity, mild reaction conditions, and maximum product yield. Moreover, the use of sodium citrate as an easily available, cheap and benign catalyst plays a pivotal role from a green perspective, considering its high recyclability and easy recovery. Therefore, this present methodology offers numerous possibilities in terms of large-scale

  摘要 柠檬酸钠作为一种高效催化剂被开发用于合成官能化的 2-氨基-3-氰基-4 H-吡喃和吡喃环化杂环。该方法涉及芳香醛、丙二腈和 1,3-二羰基化合物与 EtOH 的一锅三组分反应：H 2O (1:1 v/v) 在室温下作为溶剂。该协议具有几个优点，例如更短的反应时间、环保溶剂的利用、操作简单、反应条件温和和产品收率最高。此外，考虑到柠檬酸钠的高可回收性和易回收性，从绿色角度来看，柠檬酸钠作为一种易于获得、廉价和良性的催化剂发挥着关键作用。因此，本方法在大规模工业合成或应用于众多有机转化方面提供了许多可能性。此外，还对产物4aa形成的机理途径进行了理论研究，以确定柠檬酸钠对DFT法反应可行性的催化作用，使用B3LYP泛函。
• 1-Methylimidazolium tricyanomethanide {[HMIM]C(CN)3} as a nano structure and reusable molten salt catalyst for the synthesis of tetrahydrobenzo[b]pyrans via tandem Knoevenagel-Michael cyclocondensation and 3,4-dihydropyrano[c]chromene derivatives
  作者：Mohammad Ali Zolfigol、Neda Bahrami-Nejad、Fatemeh Afsharnadery、Saeed Baghery

  DOI：10.1016/j.molliq.2016.06.069

  日期：2016.9

  An expeditious, experimentally simple and rapid 1-methylimidazolium tricyanomethanide [HMIM]C(CN)3} nano molten salt (NMS) catalyzed tandem Knoevenagel-Michael cyclocondensation procedure for the synthesis of tetrahydrobenzo[b]pyrans was described via reaction between dimedone, aromatic aldehyde and malononitrile under solvent-free conditions at room temperature. Furthermore, 3,4-dihydropyrano[c]chromene

  通过二甲酮之间的反应，描述了一种快速，实验简单且快速的三氰基甲基1-甲基咪唑鎓[HMIM] C（CN）3 }纳米熔融盐（NMS）催化串联Knoevenagel-Michael环缩合反应合成四氢苯并[ b ]吡喃的方法，室温下在无溶剂条件下的芳族醛和丙二腈。此外，在相同条件下，以[HMIM] C（CN）3 } NMS为催化量，通过4-羟基香豆素，芳香醛和丙二腈的缩合反应合成了3,4-二氢吡喃并[ c ]色烯衍生物。
• One-pot synthesis of tetrahydro-4H-chromenes by supramolecular catalysis in water
  作者：Yufeng Ren、Wei Zhang、Jun Lu、Kai Gao、Xiali Liao、Xiaozhen Chen

  DOI：10.1039/c5ra14385c

  日期：——

  Tetrahydro-4H-chromenes were synthesizedviaan efficient one-pot three-component protocol by supramolecular catalysis with β-cyclodextrin in water.

  四氢-4H-色酮通过β-环糊精在水中进行高效一锅三组分协同催化合成。
• 2-Hydroxyethyl-1-ammonium 3-hydroxypropane-1-sulfonate: a biodegradable and recyclable ionic liquid for the one-pot synthesis of 2-amino-3-cyano-4H-pyrans
  作者：Moones Honarmand、Andromachi Tzani、Anastasia Detsi

  DOI：10.1007/s13738-018-1537-2

  日期：2019.3

  2-Hydroxyethyl-1-ammonium 3-hydroxypropane-1-sulfonate ‘HAHS’ was synthesized as a novel ionic liquid and characterized by various techniques. ‘HAHS’ ionic liquid was efficiently applied as a multifunctional promoter for the three-component synthesis of 2-amino-3-cyano-4H-pyrans. The 2-amino-3-cyano-4H-pyrans were produced not only in high to excellent yields but also no toxic solvent or catalyst was used. ‘HAHS’ ionic liquid was recovered and reused four times without the considerable decreasing in its activity. The effect of hydroxyl groups in the structure of ‘HAHS’ ionic liquid on its catalytic activity was studied. Moreover, the biodegradability potential of the ionic liquid was examined using the 5-day biological oxygen demand closed bottle test and the results showed that ‘HAHS’ has remarkable biodegradability potential.

  2-羟乙基-1-铵-3-羟基丙烷-1-磺酸盐（HAHS）作为一种新型离子液体被合成，并通过多种技术手段进行了表征。HAHS离子液体被高效应用于2-氨基-3-氰基-4H-吡喃的三组分合成中，不仅产率从高到极佳，而且无需使用有毒溶剂或催化剂。HAHS离子液体可回收并重复使用四次，活性无显著下降。研究了HAHS离子液体结构中的羟基对其催化活性的影响。此外，通过5天生物需氧量闭瓶测试考察了该离子液体的生物降解潜力，结果显示HAHS具有显著的生物降解潜力。