2-amino-4-(2-bromophenyl)-5,6,7,8-tetrahydro-5-oxo-4H-chromene-3-carbonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-amino-4-(2-bromophenyl)-5,6,7,8-tetrahydro-5-oxo-4H-chromene-3-carbonitrile
• 英文别名: 2-amino-4-(2-bromophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；2-amino-3-cyano-4-(2-bromo phenyl)-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran；2-amino-4-(2-bromophenyl)-5-oxo-4,6,7,8-tetrahydrochromene-3-carbonitrile
• 化学式: C₁₆H₁₃BrN₂O₂
• 分子量: 345.195
• InChiKey: MQDSODDFIFKHHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-环己二酮 、 邻溴苯甲醛 、 丙二腈 以 水 为溶剂， 反应 0.75h， 以93%的产率得到2-amino-4-(2-bromophenyl)-5,6,7,8-tetrahydro-5-oxo-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  通过非催化一锅三组分反应高效合成2-氨基-3-氰基-4H-吡喃衍生物

  摘要：

  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

  DOI：

  10.1007/s11164-017-3151-9

文献信息

• 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
• Sodium Benzenesulfinates: Novel and Effective Organo Catalyst for Three Component Synthesis 5,6,7,8-Tetrahydro-4H-chromene Derivatives Under Ultrasound Irradiation
  作者：Mehdi Abaszadeh、Mohammad Seifi

  DOI：10.2174/1570178612666150203004727

  日期：2015.3.24

  Sodium benzenesulfinates, as a new organo catalyst, can be used to synthesize tetrahydro- 4H-chromene derivatives by three component reaction of cyclic β-dicarbonyl compounds, malononitrile, and aromatic aldehydes, in H2O/EtOH, under ultrasound irradiation at room temperature. Inexpensiveness, stability and the potential of being easily obtained can be noted as preponderance of these catalysts. Furthermore, high conversions, short reaction times and cleaner reaction profiles are some of the advantages of this method. Moreover, H2O/EtOH (7:3) was selected as a green solvent.

  亚磺酸钠苯作为一种新型有机催化剂，可在室温下超声辐射条件下，在水/乙醇混合溶剂中，通过环状β-二羰基化合物、丙二腈和芳香醛的三组分反应来合成四氢-4H-苯并吡喃衍生物。这类催化剂的优势在于价格低廉、稳定性好且容易获得。此外，该方法具有转化率高、反应时间短和反应更清洁等优点。同时，水/乙醇(7:3)混合物被选为绿色溶剂。
• Two ligand oxidio-vanadium(IV) complexes as novel efficient catalysts in multicomponent reactions for synthesis of tetrahydrobenzopyran derivatives
  作者：M. Abaszadeh、M. Seifi、S. Y. Ebrahimipour

  DOI：10.4314/bcse.v30i2.9

  日期：——

  Two ligand oxido-vanadium(IV) complexes, [VO(L)(bipy)] (Ι) and [VO(L)(phen)] (ΙΙ); [H2L:    4-bromo-2-(((5-chloro-2-hydroxyphenyl)imino)methyl)phenol, bipy: 2,2’-bipyridine and phen: 1,10- phenanthroline], have been synthesized and characterized by elemental analysis, FT-IR, UV-Vis and conductivity measurements. These complexes, as new catalysts, were also used to synthesize the tetrahydrobenzopyran derivatives by three-component reaction of cyclic β-dicarbonyl compounds, malononitrile and aromatic aldehydes, in EtOH, at reflux. Inexpensiveness, stability and the potential of being easily obtained can be noted as preponderance of these catalysts. Furthermore, high conversions, short reaction times and cleaner reaction profiles, are some of the advantages of this method. These catalysts can be recovered and reused several times without loss of activity.

  已合成并表征了两个双配体氧化钒(IV)配合物[VO(L)(bipy)] (I)和[VO(L)(phen)] (II)；[H2L为4-溴-2-(((5-氯-2-羟基苯基)亚氨基)甲基)苯酚，bipy为2,2'-联吡啶，phen为1,10-菲罗啉]。通过元素分析、傅里叶红外光谱、紫外-可见光谱和电导率测量对这些配合物进行了表征。 这些配合物作为新型催化剂，被用于在乙醇回流条件下，通过环状β-二羰基化合物、丙二腈和芳香醛的三组分反应合成四氢苯并吡喃衍生物。这些催化剂的优势在于价格低廉、稳定性好且易于获得。此外，该方法的优点包括高转化率、反应时间短和更清洁的反应过程。这些催化剂可以回收并重复使用多次而不会失去活性。
• SO3H-dendrimer functionalized magnetic nanoparticles (Fe3O4@D NH (CH2)4SO3H): Synthesis, characterization and its application as a novel and heterogeneous catalyst for the one-pot synthesis of polyfunctionalized pyrans and polyhydroquinolines
  作者：Behrooz Maleki、Oliver Reiser、Ehsan Esmaeilnezhad、Hyoung Jin Choi

  DOI：10.1016/j.poly.2019.01.055

  日期：2019.4

  In this study, novel SO3H-dendrimer functionalized magnetic nanoparticles (Fe3O4@D-NH- (CH2)(4) SO3H) were prepared and characterized by using FT-IR, X-ray diffraction patterns, scanning electron microscopy, transmission electron microscopy, thermogravimetry analysis, and energy-dispersive X-ray spectroscopy. The synthesized nanosized catalyst was successfully applied to the synthesis of highly substituted pyrans and polyhydroquinolines via a straightforward one-pot multicomponent condensation reaction. The key advantages are the short reaction time, high yields, simple workup, and purification of products by simple recrystallization from ethanol. (C) 2019 Elsevier Ltd. All rights reserved.