2-amino-4-(4-ethoxyphenyl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile | 314767-26-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-amino-4-(4-ethoxyphenyl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile
• 英文别名: 2-amino-4-(4-ethoxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；2-amino-4-(4-ethoxyphenyl)-7,7-dimethyl-5-oxo-6,8-dihydro-4H-chromene-3-carbonitrile
• CAS: 314767-26-5
• 化学式: C₂₀H₂₂N₂O₃
• 分子量: 338.406
• InChiKey: DHFHPYAMOLEBRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 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：
  85.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-乙氧基苯甲醛 、 5,5-二甲基-1,3-环己二酮 、 丙二腈 在 C₉H₁₈N₂O₃PolSi⁽¹⁺⁾*Cl^(1-) 作用下， 以 乙醇 为溶剂， 反应 0.92h， 以91%的产率得到2-amino-4-(4-ethoxyphenyl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  二氧化硅键合的正丙基-4-氮杂-1-氮杂双环[2.2.2]辛烷氯化物（SB-DABCO）：一种高效，可重复使用的新型多相催化剂，用于合成4 H-苯并[ b ]吡喃衍生物

  摘要：

  3-氯丙基二氧化硅与二氮杂双环[2.2.2]辛烷在干燥丙酮中的反应提供了与二氧化硅键合的正丙基-4-氮杂-1-氮杂双环[2.2.2]辛烷氯化物（SB-DABCO），作为一种新的碱性催化剂。通过环酮/ 1,3-二酮与芳族醛和丙二酸烷基酯的一锅三组分反应，该催化剂可用于高效合成4 H-苯并[ b ]吡喃衍生物。

  DOI：

  10.1016/j.apcata.2011.04.012

文献信息

• Silica-bonded 5-n-propyl-octahydro-pyrimido[1,2-a]azepinium chloride (SB-DBU)Cl as a highly efficient, heterogeneous and recyclable silica-supported ionic liquid catalyst for the synthesis of benzo[b]pyran, bis(benzo[b]pyran) and spiro-pyran derivatives
  作者：Alireza Hasaninejad、Nooshin Golzar、Maryam Beyrati、Abdolkarim Zare、Mohammad Mahdi Doroodmand

  DOI：10.1016/j.molcata.2013.02.022

  日期：2013.6

  The reaction of 3-chloropropyl silica (SilprCl) with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in dry acetone affords silica-bonded 5-n-propyl-octahydro-pyrimido[1,2-a]azepinium chloride (SB-DBU)Cl as a new silica-supported ionic liquid catalyst. Afterward, (SB-DBU)Cl is used for the efficient synthesis of 4H-benzo[b]pyran derivatives via the one-pot, three-component reaction of carbonyl compounds (cyclohexane-1

  3-氯丙基二氧化硅（SilprCl）与1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）在干燥的丙酮中的反应得到二氧化硅键合的5-正丙基-八氢-嘧啶基[1,2- a]氯化ze嗪（SB-DBU）Cl作为新型的二氧化硅负载型离子液体催化剂。之后，（SB-DBU）Cl通过羰基化合物（环己烷-1,3-二酮，5,5-一锅法）的三锅法有效合成4 H-苯并[ b ]吡喃衍生物。（1，3-二甲基环己烷-1，3-二酮或3-甲基-1-苯基-2-吡唑啉-5-酮）与芳族醛和烷基丙二酸酯。此外，一些新颖的双（苯并[ b使用（SB-DBU）Cl合成[] pyran] s和在结构上含有羟吲哚和/或喹喔啉部分的多种结构多样的螺-吡喃。将催化剂循环使用十五次，收率不变。
• Glycerol as a biodegradable and reusable promoting medium for the catalyst-free one-pot three component synthesis of 4H-pyrans
  作者：Hamid Reza Safaei、Mohsen Shekouhy、Sudabeh Rahmanpur、Athar Shirinfeshan

  DOI：10.1039/c2gc35135h

  日期：——

  Glycerol is applied as a green, biodegradable and reusable promoting medium for one-pot three component synthesis of 4H-pyrans under catalyst-free conditions. A broad range of substrates including aromatic and heteroaromatic aldehydes, isatine derivatives, acenaphthenequinone and ninehydrine are condensed with carbonyl compounds possessing a reactive α-methylene group and alkylmalonates. All reactions are completed in short times, and the products are obtained in good to excellent yields. The reaction medium could be recycled and reused several times without any loss of efficiency.

  甘油作为绿色、生物可降解且可重复利用的促进介质，在无催化剂条件下用于一锅法三组分合成4H-吡喃。广泛的一系列底物，包括芳香和杂环醛、吲哚醌衍生物、苊醌和九氢吲哚，与具有活性α-亚甲基的羰基化合物及烷基丙二酸酯进行缩合反应。所有反应均在短时间内完成，产物收率良好至优异。反应介质可回收并重复使用多次，效率无任何损失。
• Efficient synthesis of novel bis(dihydropyrano[2,3c]pyrazoles), bis(4H-chromenes) and bis(dihydropyrano[3,2-c]chromenes) with amide functionality
  作者：Amna M. Abdella、Amr M. Abdelmoniem、Holger Butenschön、Ismail A. Abdelhamid、Ahmed H. M. Elwahy

  DOI：10.24820/ark.5550190.p011.071

  日期：——

  A synthesis of novel bis(1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles), bis(4H-chromene-3-carbonitriles) and bis(dihydropyrano[3,2-c]chromenes), which are linked to aliphatic spacers via amide linkages was achieved via multicomponent reactions (MCR) of the appropriate bis-aldehyde with two equivalents of both of malononitrile and 3-methylpyrazol-5-one, dimedone or 4-hydroxycoumarin in a basic solution

  合成新型双（1,4-二氢吡喃并[2,3-c]吡唑-5-腈）、双（4H-色烯-3-腈）和双（二氢吡喃并[3,2-c]色烯），其中通过酰胺键连接到脂肪族间隔基是通过适当的双醛与两当量的丙二腈和 3-甲基吡唑-5-酮、二甲酮或 4-羟基香豆素在碱性溶液中的多组分反应 (MCR) 实现的。
• Amine-functionalized hyper-crosslinked polyphenanthrene as a metal-free catalyst for the synthesis of 2-amino-tetrahydro-4 H -chromene and pyran derivatives
  作者：Reddi Mohan Naidu Kalla、Anuraj Varyambath、Mi Ri Kim、Il Kim

  DOI：10.1016/j.apcata.2017.03.009

  日期：2017.5

  the polymerization of phenanthrene using bromomethyl methyl ether as a bridging agent in the absence of any templates. The organic spheres were subjected to amine-functionalizing on the periphery of them using unreacted bromomethyl groups. The amine-functionalized microporous polyphenthrene could be employed as a highly effective and stable solid basic catalyst for the syntheses of functionalized 2-

  通过在没有任何模板的情况下使用溴甲基甲基醚作为桥联剂，通过菲的聚合，可以简单地制备超交联的微孔聚菲球。使用未反应的溴甲基基团对有机球在其外围进行胺官能化。该胺官能化的微孔polyphenthrene可以采用作为用于官能化的2-氨基四氢-4-的合成的高度有效和稳定的固体碱性催化剂ħ -色烯并吡喃衍生物。这些反应的显着特征是产品收率高，环境友好，反应时间短，底物范围广以及不需要有毒溶剂。此外，催化剂可以重复使用多达四次，而不会显着降低活性。
• Diethylene glycol-bis(3-methylimidazolium) dihydroxide as a dicationic ionic liquid catalyst for the synthesis of 4H-pyrane derivatives in aqueous medium
  作者：Khodabakhsh Niknam、Mohsen Khataminejad、Fariba Zeyaei

  DOI：10.1016/j.tetlet.2015.12.034

  日期：2016.1

  Diethylene glycol-bis(3-methylimidazolium) dihydroxide [DiEG(mim)(2)[OH](2) was prepared by the reaction between sodium hydroxide and diethylene glycol-bis(3-methylimidazolium) dibromide in aqueous ethanol at room temperature. This solid, quaternized ionic liquid was employed as a recyclable catalyst for the synthesis of 4H-pyrane derivatives in high yields from the three-component condensation reaction of malononitrile, aromatic aldehydes, and 1,3-dicarbonyls in water at room temperature. In addition, spiropyrane derivatives were synthesized from the reaction of isatin, malononitrile, and 1,3-dicarbonyls in water at reflux. The dicationic ionic liquid showed the same efficiency when used in consecutive reactions. (C) 2015 Elsevier Ltd. All rights reserved.