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

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-7,7-dimethyl-5-oxo-4-(2-phenylethyl)-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
• 英文别名: 2-Amino-7,7-dimethyl-5-oxo-4-phenethyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；2-amino-7,7-dimethyl-5-oxo-4-(2-phenylethyl)-6,8-dihydro-4H-chromene-3-carbonitrile
• 化学式: C₂₀H₂₂N₂O₂
• 分子量: 322.407
• InChiKey: USIXZOLLUCSZLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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-7,7-dimethyl-5-oxo-4-(2-phenylethyl)-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 、 4-溴-2-氯乙酰苯胺 在 potassium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 以3.8 g的产率得到2-(2-amino-3-cyano-7,7-dimethyl-5-oxo-4-(2-phenylethyl)-5,6,7,8-tetrahydro-4H-chromen-6-yl)-N-(4-bromophenyl)acetamide
  参考文献：
  名称：

  Multicomponent Syntheses of Cycloalka[b]pyridines and Chromenes

  摘要：

  DOI：

  10.1134/s1070428023070060
• 作为产物：
  描述：

  苯丙醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 2-amino-7,7-dimethyl-5-oxo-4-(2-phenylethyl)-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  Multicomponent Syntheses of Cycloalka[b]pyridines and Chromenes

  摘要：

  DOI：

  10.1134/s1070428023070060

文献信息

• 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。
• Introduction of Succinimide as A Green and Sustainable Organo-Catalyst for the Synthesis of Arylidene Malononitrile and Tetrahydrobenzo[b] pyran Derivatives
  作者：Fariba Hassanzadeh、Farhad Shirini、Manouchehr Mamaghani、Nader Daneshvar

  DOI：10.2174/1386207323666200709170916

  日期：2021.1.13

  Objective: In this work, we tried to introduce a non-toxic and stable organic compound named succinimide as a green and efficient organo-catalyst for the promotion of the synthesis of arylidene malononitrile and tetrahydrobenzo[b]pyran derivatives. Using this method led to a clean procedure to achieve these types of bioactive compounds without a specific purification step. The rate and yield of the reactions

  目的与目的：在这项工作中，我们试图引入一种无毒且稳定的有机化合物琥珀酰亚胺作为一种绿色高效的有机催化剂，用于促进亚芳基丙二腈和四氢苯并[b]吡喃衍生物的合成。使用这种方法可以通过清洁程序获得这些类型的生物活性化合物，而无需特定的纯化步骤。反应的速率和产率非常好，而且琥珀酰亚胺作为催化剂也表现出可接受的可重复使用性。 材料和方法：在 25 mL 圆底烧瓶中，[A：芳香醛 (1 mmol)、丙二腈 (1.1 mmol) 的混合物和 B：芳香醛 (1.0 mmol)、丙二腈 (1.1 mmol) 的混合物]和琥珀酰亚胺 (0.2 mmol) 在 H2O/EtOH [5 mL (1:1)] 中的溶液在 80 °C 下搅拌适当的时间。反应完成后，TLC监测[正己烷-乙酸乙酯(7:3)]，将混合物冷却至室温，过滤固体产物，用冷蒸馏水洗涤数次，得到相应的纯产品。 结果：优化催化剂的条件和用量后，一系列含
• Introduction of a new bis-derivative of succinimide (Bis-Su) as a sustainable and efficient basic organo-catalyst for the synthesis of arylidene malononitrile and tetrahydrobenzo[b]pyran derivatives under green conditions
  作者：Fariba Hassanzadeh、Nader Daneshvar、Farhad Shirini、Manouchehr Mamaghani

  DOI：10.1007/s11164-020-04235-3

  日期：2020.11

  Organo-catalysts have been under great consideration for many years because of their performance and selectivity in the reactions. In this work, a new bis-succinimide (Bis-Su) compound is prepared, identified and used as a green and efficient basic organo-catalyst for the promotion of the synthesis of arylidene malononitrile and tetrahydrobenzo[b]pyran derivatives. Using this method, both of the reactions were performed under mild conditions, during short reaction times in high yields. The catalyst can also be recycled and reused several times without a considerable decrease in its activity.

  有机催化剂因其反应性能和选择性多年来一直备受关注。在本研究中，我们制备、鉴定并利用一种新型双琥珀酰亚胺（Bis-Su）化合物作为绿色高效的基本有机催化剂，用于促进芳亚甲基丙二腈和四氢苯并[b]吡喃衍生物的合成。通过这种方法，两种反应均在温和条件下以高产率和较短的反应时间完成。催化剂还可回收并多次重复使用，其活性无显著下降。
• Aqua-mediated multicomponent synthesis of various 4H-pyran derivatives catalyzed by poly(4-vinylpyridine)-supported copper iodide nanoparticle catalyst
  作者：Jalal Albadi、Azam Mansournezhad

  DOI：10.1007/s11164-015-2400-z

  日期：2016.6

  A green and efficient approach for synthesis of some new 4 H -pyran derivatives is reported, catalyzed by green recyclable poly(4-vinylpyridine)-supported copper iodide nanoparticle catalyst in water. This procedure has many advantages such as operational simplicity, short reaction time, clean procedure, and high product yield.

  报道了一种绿色高效合成一些新的4 H- 吡喃衍生物的方法，该方法由绿色可回收的聚（4-乙烯基吡啶）负载的碘化铜纳米粒子催化剂在水中催化。该过程具有许多优点，例如操作简单，反应时间短，清洁过程和高产物产率。
• One-pot synthesis of substituted 4 H -chromenes by nickel ferrite nanoparticles as an efficient and magnetically reusable catalyst
  作者：Ahankar, Hamideh、Ramazani, Ali、Slepokura, Katarzyna、Lis, Tadeusz、Joo, Sang Woo

  DOI：10.3906/kim-1710-14

  日期：——

  Nickel ferrite magnetic nanoparticles (NiFe$_2}$O$_4}$ MNPs) were prepared via the autocombustion assisted sol-gel method. The efficient catalyst was investigated by FT-IR, XRD, ICP, SEM, and TEM techniques. A one-pot, three-component reaction is reported for the synthesis of substituted 4$H$-chromenes in the presence of NiFe$_2}$O$_4}$ MNPs as a reusable catalyst in a green solvent at 40 $^\circ}$C under clean, efficient, and mild conditions. Furthermore, selected products were characterized by FT-IR, $^1}$H NMR, and $^13}$C NMR. The single-crystal X-ray analysis of product 4u was also conclusively confirmed. Easy workup procedure, high purity of products via simple recrystallization, and environmentally benign conditions are the outstanding benefits of this method.

  镍铁氧体磁性纳米颗粒（NiFe$_2}$O$_4}$ MNPs）是通过自燃辅助溶胶-凝胶法制备的。这种高效催化剂通过FT-IR、XRD、ICP、SEM和TEM技术进行了研究。报告了一种一锅法三组分反应，利用NiFe$_2}$O$_4}$ MNPs作为可重复使用的催化剂，在40 $^\circ}$C的绿色溶剂中，在清洁、高效和温和的条件下合成取代的4$H$-色烯。此外，选择的产品通过FT-IR、$^1}$H NMR和$^13}$C NMR进行了表征。产品4u的单晶X射线分析也得到了确凿的确认。该方法的突出优点包括简单的操作步骤、高纯度的产品通过简单重结晶获得，以及环保友好的条件。