2-amino-4-(3-bromophenyl)-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-(3-bromophenyl)-4a,5,6,7-tetrahydronaphthalene-1,3,3(4H)-tricarbonitrile
• 英文别名: 2-amino-4-(3-bromophenyl)-4a,5,6,7-tetrahydro-4H-naphthalene-1,3,3-tricarbonitrile
• 化学式: C₁₉H₁₅BrN₄
• 分子量: 379.259
• InChiKey: XRDKIBUWSWAVAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  间溴苯甲醛 、 环己酮 、 丙二腈 在 N-butylpyridinium tetrafluoroborate 作用下， 反应 5.0h， 以88%的产率得到2-amino-4-(3-bromophenyl)-4a,5,6,7-tetrahydronaphthalene-1,3,3(4H)-tricarbonitrile
  参考文献：
  名称：

  离子液体中双环邻氨基甲腈衍生物的串联合成

  摘要：

  通过一当量的芳族醛，环己酮和两当量的丙二腈的串联四组分缩合反应，可高效合成2-氨基-4a，5,6,7-四氢萘-1,3,3 （4 H）-三腈在离子液体中进行。一锅中最多形成四个新的键和一个新的环，而水是该多组分方法中唯一的副产物。

  DOI：

  10.1002/jhet.2088

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。
• 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。
• Synthesis of orthoaminocarbonitrile tetrahydronaphthalenes catalyzed by butyl-3-methylimidazolium hexafluorophosphate ionic liquid base catalyst
  作者：Mahsa Khorasani、Hossein Naeimi

  DOI：10.1080/00397911.2022.2119579

  日期：2022.10.18

  Abstract In this research, the treatment of cyclohexanone, malononitrile, and aromatic aldehydes was carried out for the successful synthesis of orthoaminocarbonitrile tetrahydronaphthalenes by using butyl-3-methylimidazolium hexafluorophosphate as a base catalyst. In this protocol, the target products were obtained in high to excellent yields between 85% and 95% and short reaction times between 10

  摘要 本研究以丁基-3-甲基咪唑鎓六氟磷酸盐为碱催化剂，对环己酮、丙二腈和芳香醛进行处理，成功合成邻氨基甲腈四氢萘。在该协议中，目标产物在温和条件下以 85% 至 95% 的高至极好产率和 10 至 20 分钟的短反应时间获得。所有产物均通过熔点、FT-IR 和1 H NMR 技术进行鉴定。
• Fabrication and characterization of mesoporous yolk–shell nanocomposites as an effective reusable heterogeneous base catalyst for the synthesis of ortho-aminocarbonitrile tetrahydronaphthalenes
  作者：Mahsa Khorasani、Hossein Naeimi

  DOI：10.1039/d3ra02740f

  日期：——

  Mesoporous yolk–shell nanocomposites (MYSNs) were loaded with a mobile CaMg core inside the silica shell. CaMg@MYS nanocomposites have been effectively prepared inside the inner cavity of a novel structure that consists of hollow mesoporous silica spheres. Tetraethyl orthosilicate (TEOS) and an amount of cetyltrimethylammonium bromide (CTAB) are coated on the carbon spheres used as a hard template

  介孔蛋黄壳纳米复合材料（MYSN）在二氧化硅壳内负载有移动的 CaMg 核。CaMg@MYS 纳米复合材料已在由中空介孔二氧化硅球组成的新颖结构的内腔内有效制备。原硅酸四乙酯（TEOS）和一定量的十六烷基三甲基溴化铵（CTAB）被涂覆在碳球上，在多步合成过程中用作硬模板。在该方法中，在温和条件下，目标产物的产率高达 87-96%，响应时间在 10-20 分钟之间。CaMg@MYS 催化剂在多组分工艺中显示出作为高效且可重复使用的催化剂的前景。与金属氧化物纳米结构相比，CaMg@MYS 多蛋黄球表现出较高的催化性能和新颖性的重要因素。应用1 H NMR和熔点技术。此外，为了表征所制备的催化剂，还应用了 FT-IR、XRD、FE-SEM、EDS、元素图谱和 HR-TEM 技术。
• Sonochemical synthesis of ortho‐aminocarbonitrile tetrahydronaphthalenes using mesoporous yolk–shell nanocomposites as a recyclable heterogeneous catalyst and evaluation of their in vitro antimicrobial activities
  作者：Mahsa Khorasani、Hossein Naeimi、Zohreh Zahraei

  DOI：10.1002/aoc.7305

  日期：2024.1

  A mobile Ca/Mg core was formed inside the silica shell of mesoporous yolk–shell nanocomposites (CaO‐MgO@SiO2). This new structure of hollow mesoporous silica spheres has been successfully synthesized inside the inner cavity. The used carbon spheres as a rigid template in the multi‐step synthetic process are covered with tetraethyl orthosilicate (TEOS) and a mixture of cetyltrimethylammonium bromide (CTAB). Then, the tetrahydronaphthalenes were synergistically synthesized using CaO‐MgO@SiO2 nanocomposites as a nanocatalyst under ultrasound irradiation. By this technique, the required items could be produced with a high to excellent efficiency between 90% and 98% and the reaction times of 5–15 min. As an effective and reusable catalyst in multicomponent processes, the CaO‐MgO@SiO2 catalyst exhibits high reactivity. The FT‐IR, 1H NMR, and melting point methods were used to identify all of the products. Moreover, FT‐IR, XRD, FE‐SEM, EDS, Mapping, and HR‐TEM techniques are used to characterize the prepared catalysts. Also, in vitro antibacterial activity of some synthetic compounds was evaluated.