2-amino-4-(furan-2-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile | 315245-12-6

• 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)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
• 英文别名: 2-amino-5,6,7,8-tetrahydro-4-(furan-2-yl)-5-oxo-4H-chromene-3-carbonitrile；2-amino-4-(2-furanyl)-5,6,7,8-tetrahydro-5-oxo-4H-chromene-3-carbonitrile；2-amino-4-furan-2-yl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；2-amino-4-(furan-2-yl)-5-oxo-4,6,7,8-tetrahydrochromene-3-carbonitrile
• CAS: 315245-12-6
• 化学式: C₁₄H₁₂N₂O₃
• 分子量: 256.261
• InChiKey: VCOFSMLXFHYCKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  碘苯二乙酸 、 2-amino-4-(furan-2-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 以 二氯甲烷 为溶剂， 反应 1.0h， 以84%的产率得到
  参考文献：
  名称：

  Facile synthesis of functionalized 6-cyano-2-oxa-7-azabicyclo[4.1.0]hept-3-en-1-yl acetates: a catalyst free approach to access the pyran fused 2-acetoxy-NH-aziridines

  摘要：

  通过在无催化剂环境下使用碘苯二乙酸酯，将4-H-吡喃和螺环吡喃的恩胺片段反应构建了新型的吡喃融合2-乙氧基-NH-环氧乙烷骨架。

  DOI：

  10.1039/c5ra24510a
• 作为产物：
  描述：

  (2-呋喃亚甲基)丙二腈 、 1,3-环己二酮 在 吗啉 作用下， 以 乙醇 为溶剂， 以70%的产率得到2-amino-4-(furan-2-yl)-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

• Evaluation of magnetically recyclable nano-Fe3O4 as a green catalyst for the synthesis of mono- and bis-tetrahydro-4H-chromene and mono and bis 1,4-dihydropyridine derivatives
  作者：Bagher Amirheidari、Mohammad Seifi、Mehdi Abaszadeh

  DOI：10.1007/s11164-015-2220-1

  日期：2016.4

  Magnetically separable Fe3O4 nanoparticles were used as an environmental friendly catalyst for the synthesis of mono- and bis-tetrahydro-4H-chromene and mono- and bis-1,4-dihydropyridine derivatives via three-component reactions of aromatic aldehydes and malononitrile with cyclic β-dicarbonyls or cyclic β-enaminoketones respectively. These reactions were carried out in EtOH and at reflux. Fe3O4 nanoparticles can be magnetically separated from the reaction mixture by a magnet and recycled without significant loss of catalytic activity.

  磁性可分离的Fe3O4纳米颗粒被用作一种环保型催化剂，用于通过芳香醛、丙二腈与环状β-二羰基化合物或环状β-烯胺酮的三组分反应，合成单/双四氢-4H-色烯衍生物和单/双1,4-二氢吡啶衍生物。这些反应在乙醇中进行并回流。Fe3O4纳米颗粒可通过磁铁从反应混合物中磁性分离，并且可以回收利用而不会显著损失催化活性。
• Efficient synthesis of 2-amino-3-cyano-4H-pyran derivatives via a non-catalytic one-pot three-component reaction
  作者：Cheng-Wei Lü、Jia-Jing Wang、Fei Li、Shi-Jun Yu、Yue An

  DOI：10.1007/s11164-017-3151-9

  日期：2018.2

  Abstract A convenient one-pot multi-component strategy was conducted successfully under catalyst-free conditions employing water and PEG-400 as the efficient and cheap promoting medium. Three types and nearly 50 2-amino-3-cyano-4H-pyran annulated derivatives were synthesized in good to excellent yields by the condensation of a series of aromatic aldehydes with malononitrile and different 1,3-dicarbonyl

  摘要 在无催化剂的条件下，使用水和PEG-400作为高效廉价的促进介质，成功地成功实施了一种方便的单锅多组分策略。通过一系列芳香醛与丙二腈和不同的1,3-二羰基化合物的缩合反应，合成了三种类型的近50种2-氨基-3-氰基-4H-吡喃环化的衍生物，收率良好。宽的底物范围，系统的表征，消除的催化剂，简短的反应时间和简单的纯化程序是该方法的最佳优点。 图形概要
• SUBSTITUTED HETEROCYCLIC COMPOUNDS
  申请人：Abelman Matthew

  公开号：US20090012103A1

  公开（公告）日：2009-01-08

  The present invention relates to novel heterocyclic compounds and to their use in the treatment of various disease states, including cardiovascular diseases and diabetes. In particular embodiments, the structure of the compounds is given by Formula (I): wherein Q1, Q2, R2, R3, R4, R5, and R6 are as described herein. The invention also relates to methods for the preparation of the compounds, and to pharmaceutical compositions containing such compounds.

  本发明涉及新颖的杂环化合物及其在治疗各种疾病状态中的应用，包括心血管疾病和糖尿病。在特定实施例中，化合物的结构由公式（I）给出：其中Q1、Q2、R2、R3、R4、R5和R6如本文所述。该发明还涉及制备这些化合物的方法，以及含有这些化合物的药物组合物。
• Synthesis, molecular modeling and BACE-1 inhibitory study of tetrahydrobenzo[b] pyran derivatives
  作者：Vijaya Bhaskar、Reshma Chowdary、Sheshagiri R. Dixit、Shrinivas D. Joshi

  DOI：10.1016/j.bioorg.2018.11.023

  日期：2019.3

  documented as one of the possible therapeutic targets for the treatment of Alzheimer's disease. In this paper, we report the synthesis and the for β-secretase (BACE-1) inhibitory activity of new series of tetrahydrobenzo [b] pyran derivatives. One-pot synthesis of tetrahydrobenzo [b] pyrans was carried out by condensing aromatic aldehyde, malononitrile and 1,3-cyclohexanedione using ionic liquid 1-butyl-3-methyl

  β-分泌酶（BACE1）已被广泛证明是治疗阿尔茨海默氏病的可能治疗靶标之一。在本文中，我们报告了新系列的四氢苯并[b]吡喃衍生物的合成及其对β-分泌酶（BACE-1）的抑制活性。一锅法合成四氢苯并[b]吡喃是通过在水性醇介质中使用离子液体1-丁基-3-甲基咪唑鎓氯化物（[bmIm] Cl-）缩合芳族醛，丙二腈和1,3-环己二酮来进行的。乙醇和水的比例为1：2，可使所有反应物保持在溶液中，这有助于反应并非常容易地形成产物。对合成的化合物进行BACE1抑制分析，六个化合物4d，4e，4f，4h，4i和4p在微摩尔水平显示出显着的IC50值。在这六种活性化合物中，4e是一种潜在的抑制剂，其IC50值在纳摩尔范围内。所有合成的化合物都停靠在β-分泌酶的活性位点上。
• Cheap thiamine hydrochloride as efficient catalyst for synthesis of 4H-benzo[b]pyrans in aqueous ethanol
  作者：Lu Chen、Sunan Bao、Lixiang Yang、Xian Zhang、Bin Li、Yibiao Li

  DOI：10.1007/s11164-016-2843-x

  日期：2017.7

  Preparation of pharmaceutically active 2-amino-4H-pyran derivatives has been achieved using cheap thiamine hydrochloride as catalyst. A wide range of aromatic aldehydes easily undergo condensation with malononitrile and several kinds of 1,3-cyclohexanedione under mild condition to afford the desired product with good purity in excellent yield. This protocol has various advantages as a simple, clean, and environmentally benign three-component process.

  利用廉价原料盐酸硫胺素作为催化剂，已经实现了具有药理活性的2-氨基-4H-吡喃衍生物的制备。多种芳香醛可以在温和条件下与丙二腈以及几种1,3-环己二酮发生缩合反应，得到纯度高且产率优异的目标产物。该方法作为一个简便、清洁且环境友好的三组分反应，具有多种优势。