2-amino-7-hydroxy-4-(thiophen2-yl)-4H-chromene-3-carbonitrile | 130944-05-7

• 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-amino-7-hydroxy-4-(thiophen2-yl)-4H-chromene-3-carbonitrile
• 英文别名: 2-amino-3-cyano-7-hydroxy-4-(2-thiophene)-4H-chromene；2-amino-3-cyano-7-hydroxy-4-(thiophenyl)-4H-chromene；2-amino-3-cyano-7-hydroxy-4-(2-thienyl)-4H-chromene；2-Amino-7-hydroxy-4-thiophen-2-yl-4H-chromene-3-carbonitrile
• CAS: 130944-05-7
• 化学式: C₁₄H₁₀N₂O₂S
• 分子量: 270.312
• InChiKey: VAIWHJBXUXCDIR-UHFFFAOYSA-N

物化性质

• 熔点：
  202-204 °C(Solv: ethanol (64-17-5))
• 沸点：
  530.1±50.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2-噻吩亚甲基)甲烷-1,1-二甲腈 、 间苯二酚 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以72%的产率得到2-amino-7-hydroxy-4-(thiophen2-yl)-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  Elagamey; El-Taweel, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 9, p. 885 - 886

  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。
• Copper‐based Schiff Base Complex Immobilized on Core‐shell Fe₃O₄@SiO₂as a magnetically recyclable and highly efficient nanocatalyst for green synthesis of 2‐amino‐4<i>H</i>‐chromene derivatives
  作者：Hakimeh Ebrahimiasl、Davood Azarifar

  DOI：10.1002/aoc.5359

  日期：2020.3

  Fe3O4‐supported copper (II) Schiff‐Base complex has been synthesized through post‐modification with 1,3‐phenylenediamine followed by further post‐modification with salicylaldehyde and coordination with Cu(II) ion. The resulted Fe3O4@SiO2‐imine/phenoxy‐Cu(II) magnetic nanoparticles (MNPs) were characterized by various techniques including SEM, TEM, XRD, XPS, EDX, VSM, FT‐IR, and ICP. The catalytic activity

  Fe 3 O 4负载的铜（II）Schiff-Base配合物的合成方法是：先用1,3-苯二胺进行后修饰，然后再用水杨醛进行后修饰，再与Cu（II）离子配位。Fe 3 O 4 @SiO 2-亚胺/苯氧基-Cu（II）磁性纳米粒子（MNPs）通过各种技术进行表征，包括SEM，TEM，XRD，XPS，EDX，VSM，FT-IR和ICP。作为一锅三组分合成2-氨基-4 H的可磁循环利用的非均相催化剂的催化活性检验了chrome色烯衍生物。该催化剂在反应中是有效的，并且可以通过磁分离回收并循环几次而不会显着降低催化活性。
• Prolinamide functionalized polyacrylonitrile fiber with tunable linker length and surface microenvironment as efficient catalyst for Knoevenagel condensation and related multicomponent tandem reactions
  作者：Hai Zhu、Gang Xu、Huimin Du、Chenlu Zhang、Ning Ma、Wenqin Zhang

  DOI：10.1016/j.jcat.2019.04.040

  日期：2019.6

  attaching amines to fiber matrix as well as the constructed hydrophobic microenvironment by linker group within the surface layers of fiber materials effectively promotes the reactions. In addition, the good swollen capacity of fiber in solvent ensure that the reaction proceed well. Fiber catalyst PANPA−2F modified by prolinamide with a C2 alkyl chain exhibited the best catalytic performance and can

  首次通过共价键合制备了一系列具有可调的烷基连接基团长度和不同连接基团的脯氨酰胺聚丙烯腈纤维催化剂，并具有良好的机械强度，FT-IR，XRD，EA，TGA，SEM和水接触角特征。在Knoevenagel缩合反应和一锅法Knoevenagel-Michael多组分串联反应中评估了这些纤维催化剂的催化活性，以合成α，β-不饱和腈和2-氨基-4 H-色烯衍生物在水中。结果表明，在纤维材料表面层中合适的连接长度的胺与纤维基质连接，以及通过连接基团构建的疏水性微环境均能有效地促进反应。另外，纤维在溶剂中的良好溶胀能力确保反应进行得很好。脯氨酰胺修饰的具有C2烷基链的纤维催化剂PAN PA-2 F表现出最佳的催化性能，可以轻松回收和再利用至少十个连续循环，而不会显着降低催化活性和浸出活性位。
• 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。