2-amino-4-(4-methylphenyl)-4a,5,6,7-tetrahydronaphthalene-1,3,3(4H)-tricarbonitrile

• 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-(4-methylphenyl)-4a,5,6,7-tetrahydronaphthalene-1,3,3(4H)-tricarbonitrile
• 英文别名: 2-amino-4a,5,6,7-tetrahydro-4-p-tolylnaphthalene-1,3,3(4H)-tricarbonitrile；2-Amino-3,3-dicyano-4-(4-methylphenyl)-4A,5,6,7-tetrahydro-1(4H)-naphthalenyl cyanide；2-amino-4-(4-methylphenyl)-4a,5,6,7-tetrahydro-4H-naphthalene-1,3,3-tricarbonitrile
• 化学式: C₂₀H₁₈N₄
• mdl: MFCD01460377
• 分子量: 314.39
• InChiKey: WIENPEIVMXUIDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  97.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(4-甲基亚苄基)-丙二腈 、 2-cyano-2-cyclohexylidenethioacetamide 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以22%的产率得到2-amino-4-(4-methylphenyl)-4a,5,6,7-tetrahydronaphthalene-1,3,3(4H)-tricarbonitrile
  参考文献：
  名称：

  Novel [4 + 2] Cycloaddition Reaction of Aryl-Methylidenemalononitriles to Unsaturated Chalcogen Amides. Synthesis, Structure, and Properties of Triethylammonium 3,5,5-Tricyano-1,4,5,6-Tetrahydropyridine-2-Selenolates and -Thiolates

  摘要：

  Reaction of arylmethylidenemalononitriles with 3-aryl-2-cyanoprop-2-eneselenoamides in the presence of Et3N gave triethylammonium 4,6-diaryl-3,5,5-tricyano-1,4,5,6-tetrahydropyridine-2-selenolates. A similar reaction with cyclohexylidenecyanothioacetamide yields triethylammonium 4-aryl-1,5,5-tri-cyano-3-azaspiro[5.5]undec-1-ene-2-thiolate. Alkylation of the obtained selenolates and thiolates gives 6-(alkylseleno)-2,4-diaryl-1,4-dihydropyridine-3,3,5(2H)-tricarbonitriles and 4-(alkylthio)-2-aryl-3-aza- spiro[5.5]undec-4-ene-1,1,5-tricarbonitriles, respectivelly. The structure of 2,4-di(2-furyl)-6-{[2-(4-methylphenyl)-2-oxoethyl]seleno}-1,4-dihydropyridine-3,3,5(2H)-tricarbonitrile has been confirmed by the X-ray structural analysis.

  DOI：

  10.1007/s10593-013-1378-y

文献信息

• Synthesis of cobalt tetra-2,3-pyridiniumporphyrazinato with sulfonic acid tags as an efficient catalyst and its application for the synthesis of bicyclic <i>ortho</i>-aminocarbonitriles, cyclohexa-1,3-dienamines and 2-amino-3-cyanopyridines
  作者：Mohammad Dashteh、Mohammad Ali Zolfigol、Ardeshir Khazaei、Saeed Baghery、Meysam Yarie、Sajjad Makhdoomi、Maliheh Safaiee

  DOI：10.1039/d0ra02172e

  日期：——

  ortho-Aminocarbonitriles, cyclohexa-1,3-dienamines and 2-amino-3-cyanopyridines were synthesized by [Co(TPPASO₃H)]Cl as an efficient pyridiniumporphyrazinato based catalyst.

  "ortho"-氨基腈、环己烯-1,3-二胺和2-氨基-3-氰基吡啶通过[Co(TPPASO3H)]Cl作为高效的吡啶基卟啉催化剂合成。
• Borax catalyzed domino reactions: synthesis of highly functionalised pyridines, dienes, anilines and dihydropyrano[3,2-c]chromenes
  作者：Aniruddha Molla、Sahid Hussain

  DOI：10.1039/c4ra03627a

  日期：——

  Borax, an innocuous, inexpensive, and a naturally occurring material, very efficiently catalyzes the Knoevenagel condensation and Michael addition in domino fashion for the construction of highly functionalised pyridines, dienes, anilines and dihydropyrano[3,2-c]chromenes. The present protocol offers advantages in terms of higher yields, wide scope of substrates, operational simplicity, short reaction time, no requirement of workup or column chromatography, and easy access to a wide range of structurally diverse functionalized molecules of biological importance. Recycling of the catalyst and scaling up of the reactions are important attributes of this catalytic process.

  硼砂是一种无害、廉价且自然存在的物质，它以串联方式高效催化Knoevenagel缩合反应和Michael加成反应，用于构建高度功能化的吡啶、二烯、苯胺和二氢吡喃[3,2-c]色烯结构。目前的协议在产量、底物范围广度、操作简便性、反应时间短、无需后处理或柱层析以及易于获得结构多样且具有生物学意义的官能化分子等方面具有优势。催化剂的回收和反应的规模放大是该催化过程的重要特点。
• Multicomponent domino reactions in deep eutectic solvent: An efficient strategy to synthesize multisubstituted cyclohexa-1,3-dienamines
  作者：Najmedin Azizi、Tahereh Soleymani Ahooie、Mohammad Mahmoudi Hashemi

  DOI：10.1016/j.molliq.2017.09.049

  日期：2017.11

  Urea-choline chloride based DES is effective dual solvents/organocatalysts and affording a series of multisubstituted cyclohexa-1,3-dienamines in good to excellent yields under mild conditions. The DES could be easily recycled several times without appreciable loss of activity. The present protocol offers advantages in terms of environmental sustainability and efficient utilization of natural resources

  研究了酮，醛和丙二腈在深共熔溶剂（DES）中的多组分多米诺反应。氯化脲-胆碱氯化物是有效的双重溶剂/有机催化剂，在温和条件下以良好或优异的收率提供了一系列多取代的环己-1,3-二烯胺。DES可以轻松回收几次，而不会造成明显的活动损失。本协议在环境可持续性和对自然资源的有效利用，操作简便和反应时间短方面具有优势。
• DABCO functionalized dicationic ionic liquid (DDIL): A novel green benchmark in multicomponent synthesis of heterocyclic scaffolds under sustainable reaction conditions
  作者：Trushant Lohar、Arjun Kumbhar、Madhuri Barge、Rajshri Salunkhe

  DOI：10.1016/j.molliq.2016.10.039

  日期：2016.12

  network enhances the overall activity of DDIL. These make them compatible for base catalyzed one pot multicomponent synthesis of ortho -amino carbonitriles and 3-methyl-4-arylmethylene-isoxazol-5(4 H )-ones under grinding without solvent. In addition the activity of DDIL was also studied for synthesis of tetrahydrobenzo[b]pyrans under ultrasound irradiation in water. Furthermore the DDIL was easily recoverable

  摘要 采用二氮杂双环[2,2,2]辛烷(DABCO)、1,3-二氯-2-丙醇和NaBF 4 在乙腈中合成了一种新型DABCO功能化双阳离子离子液体(DDIL)。IL 已通过 IR、NMR 和质谱技术充分表征。IL 中BF 4 - 阴离子的存在通过 19 F NMR 证实并且也得到质量分析的支持。TGA 分析表明，IL 在高达 180 °C 的温度下是热稳定的。我们证明了 DDIL 网络中叔氮位点和羟基的存在增强了 DDIL 的整体活性。这些使它们与碱催化的邻氨基腈和 3-甲基-4-芳基亚甲基-异恶唑-5(4 H )-在无溶剂研磨下的一锅多组分合成相容。此外，还研究了 DDIL 在水中超声照射下合成四氢苯并[b]吡喃的活性。此外，DDIL 易于多次回收和回收，活性适度降低。
• A task-specific biodegradable ionic liquid: a novel catalyst for synthesis of bicyclic ortho-aminocarbonitriles
  作者：D. S. Gaikwad、K. A. Undale、D. B. Patil、A. A. Patravale、A. A. Kamble

  DOI：10.1007/s13738-018-1315-1

  日期：2018.5

  AbstractHerein, we report a novel method for synthesis of bicyclic ortho-aminocarbonitriles catalyzed by biodegradable ionic liquid. The biodegradability (BOD analysis) of all the ionic liquids that are used to carry out the reaction is studied, and these ester-functionalized ionic liquids showed better degradability as compared to the rest of the ILs. The IL used in the reaction was recycled six times

  摘要本文中，我们报道了一种可生物降解的离子液体催化合成双环邻氨基甲腈的新方法。研究了用于进行反应的所有离子液体的生物降解性（BOD分析），并且与其他ILs相比，这些酯官能化的离子液体显示出更好的降解性。反应中使用的IL非常有效地循环了六次，并且开发的方法在绿色化学指标计算（AE，RME，MI，CE，TON和TOF）方面也很有效。高收率，更少的时间且无需柱色谱法是该方案的附加优点。 图形概要