2-amino-4-(2,4-dichlorophenyl)-5,6,7,8-tetrahydro-7,7-dimethyl-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-(2,4-dichlorophenyl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile
• 英文别名: 2‑amino‑3‑cyano‑7,7‑dimethyl‑4‑(2,4‑dichlorophenyl)‑5‑oxo‑4H‑5,6,7,8‑tetrahydro benzopyran；2-amino-4-(2,4-dichlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8- tetrahydro-4H-chromene-3-carbonitrile；2-amino-3-cyano-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4-(2',4'-dichlorophenyl)-4H-benzo[b]pyran；2-amino-4-(2,4-dichlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；2-amino-7,7-dimethyl-4-(2,4-dichlorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；2-amino-3-cyano-4-(2,4-dichlorophenyl)-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydro-benzo[b]-pyran；2-amino-4-(2,4-dichlorophenyl)-7,7-dimethyl-5-oxo-6,8-dihydro-4H-chromene-3-carbonitrile
• 化学式: C₁₈H₁₆Cl₂N₂O₂
• 分子量: 363.243
• InChiKey: BFRHMJODPKAZTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-4-(2,4-dichlorophenyl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile 在 甲酸 、 硫酸 、 水 作用下， 反应 2.0h， 以61%的产率得到3-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3-(2,4-dichlorophenyl)propanoic acid
  参考文献：
  名称：

  某些含有2-氨基-3-氰基-4 H-吡喃体系的熔融和螺化合物的水解降解

  摘要：

  加热-5,6,7,8-四氢-4-的一些衍生物Н色烯和1,2,5-'，6'，7'，8'- hexahydrospiro- [吲哚-3,4'-吡喃]在酸环境会导致水解降解并形成功能性取代的羧酸。在相同条件下的1,2-二氢螺并[吲哚-3,4'-吡喃]衍生物提供了由逆迈克尔分解和再循环产生的产物混合物。

  DOI：

  10.1134/s1070428018050251
• 作为产物：
  描述：

  2,4-二氯苯甲醛 在 potassium fluoride dihydrate 作用下， 以 乙醇 为溶剂， 生成 2-amino-4-(2,4-dichlorophenyl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  新型9,9-二甲基-8,12-二氢-9 H-色基[3,2- e ][1,2,4]三唑并[1,5 - c ]嘧啶-11(10 H )-one的合成衍生品

  摘要：

  9,9-二甲基-8,12-二氢-9H-色基[3,2-e][1,2,4]三唑并[1,5-c]嘧啶-11(10H)-one衍生物的合成原甲酸三乙酯或芳香醛与色诺[2,3-d]嘧啶衍生物的反应，其由一水合肼和甲酰亚胺衍生物反应制备。通过 2-氨基-7,7-二甲基-5-氧代-4-芳基-5,6,7,8-四氢-4H-色烯-3-腈衍生物和原甲酸三乙酯的反应合成甲酰亚胺。12-(4-甲氧基苯基)-9,9-二甲基-8,12-二氢-9H-色基[3,2-e][1,2,4]三唑并[1,5-c]嘧啶- 11(10H)-one是通过单晶X射线衍射分析确定的。

  DOI：

  10.3184/174751914x14053476598397

文献信息

• 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。
• Magnetic core–shell titanium dioxide nanoparticles as an efficient catalyst for domino Knoevenagel–Michael-cyclocondensation reaction of malononitrile, various aldehydes and dimedone
  作者：Ardeshir Khazaei、Fatemeh Gholami、Vahid Khakyzadeh、Ahmad Reza Moosavi-Zare、Javad Afsar

  DOI：10.1039/c4ra16300a

  日期：——

  Magnetic core–shell titanium dioxide nanoparticles (Fe3O4@SiO2@TiO2) were efficiently used for the preparation of tetrahydrobenzo[b]pyran derivatives via a one-pot three component condensation reaction of various aldehydes, dimedone and malononitrile at 100 °C under solvent-free conditions. The catalyst was synthesized and characterized by several techniques including X-ray diffraction (XRD), transmission

  磁性核-壳二氧化钛纳米颗粒（Fe 3 O 4 @SiO 2 @TiO 2）可通过各种浓度的醛，二甲酮和丙二腈的一锅三组分缩合反应有效地用于制备四氢苯并[ b ]吡喃衍生物。无溶剂条件下的℃。通过几种技术合成并表征了催化剂，包括X射线衍射（XRD），透射电子显微镜（TEM），场发射扫描电子显微镜（FESEM）和能量色散X射线光谱（EDX）。
• Silica-supported Phosphomolybdic Acid-catalyzed Efficient Synthesis of 1,8-Dioxooctahydroxanthene and Tetrahydrochromene Derivatives
  作者：Biswanath Das、Martha Krishnaiah、Keetha Laxminarayana、Kongara Damodar、Duddukuri Nandan Kumar

  DOI：10.1246/cl.2008.1000

  日期：2008.9.5

  Silica-supported phosphomolybdic acid was found to be an efficient heterogeneous catalyst for the synthesis of 1,8-dioxooctahydroxanthenes from aldehydes and dimedone and of tetrahydrochromenes fro...

  发现二氧化硅负载的磷钼酸是一种有效的多相催化剂，可用于从醛和二甲酮合成 1,8-二氧代辛基羟基氧杂蒽以及从...
• 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。
• Improvement in nanocomposite host (nanocavity of dealuminated zeolite Y)-guest (12-molybdophosphoric acid) catalytic activity and its application to the one-pot three-component synthesis of tetrahydrobenzo[ b ]pyrans
  作者：Seyedeh Fatemeh Hojati、Maryam Moosavifar、Toktam Ghorbanipoor

  DOI：10.1016/j.crci.2016.11.005

  日期：2017.5

  efficient chemoselective synthesis of tetrahydrobenzo[b]pyran derivatives, and the corresponding products were obtained in good to excellent yields in very short reaction times. Furthermore, the catalytic activity of this new catalyst in the synthesis of tetrahydrobenzo[b]pyrans was compared with MPA encapsulated in zeolite Y dealuminated by the hydrothermal method. The catalyst (MPA–MDAZY) was recovered

  摘要 采用化学方法（乙二胺四乙酸）对沸石 Y 进行脱铝，以修饰沸石结构，以负载 12-磷酸钼酸 (MPA)。MPA 封装在改性脱铝沸石 Y (MDAZY) 的纳米腔中，并通过傅里叶变换红外、X 射线衍射和原子吸收光谱进行表征。新催化剂用于四氢苯并[b]吡喃衍生物的高效化学选择性合成，并在很短的反应时间内以良好至极好的收率获得了相应的产物。此外，将这种新催化剂在四氢苯并[b]吡喃合成中的催化活性与包封在通过水热法脱铝的沸石Y中的MPA进行了比较。