N-cyclohexyl-3,4-dihydro-3,3-dimethylquinoxalin-2-amine | 1011487-24-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-cyclohexyl-3,4-dihydro-3,3-dimethylquinoxalin-2-amine
• 英文别名: N-cyclohexyl-3,3-dimethyl-3,4-dihydroquinoxalin-2-amine；N-cyclohexyl-3,3-dimethyl-1,4-dihydroquinoxalin-2-imine
• CAS: 1011487-24-3
• 化学式: C₁₆H₂₃N₃
• 分子量: 257.379
• InChiKey: PQMBCLCFCQCQAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  36.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  异氰环已烷 、 邻苯二胺 、 丙酮 以 乙醇 为溶剂， 反应 0.2h， 以98%的产率得到N-cyclohexyl-3,4-dihydro-3,3-dimethylquinoxalin-2-amine
  参考文献：
  名称：

  Co3O4 @ SiO2核壳纳米粒子在超声辐照下快速高效地一锅合成3,4-二氢喹喔啉-2-胺衍生物

  摘要：

  在这项研究中，使用Co3O4 @ SiO2纳米粒子在超声辐射下开发了一种通用的合成3,4-二氢喹喔啉-2-胺衍生物的合成方法。首先通过简单，绿色的工艺，通过超声处理制备Co3O4; @ SiO2纳米粒子，然后将它们用作邻苯二胺（OPDA）的三组分反应合成3,4-二氢喹喔啉-2-胺的有效催化剂。 ），超声辐照下乙醇中的各种酮和各种异氰酸酯。通过在使用乙醇作为绿色环境的同时施加超声辐射，可以实现该程序的组合合成。本方法提供了许多优点，例如高收率，对环境无害，后处理简单，产物的收率极好并且反应时间短。可以使用简单的外部磁体容易地回收纳米磁性催化剂，并重复使用几次而活性没有任何显着损失。通过FT-IR，FE-SEM，XRD，EDX，VSM和TEM分析对催化剂进行了全面表征。

  DOI：

  10.2174/1386207319666160524141831

文献信息

• Guanidinium-based sulfonic acid as a new Brønsted acid organocatalyst in organic synthesis in water
  作者：Mozhdeh Seyyedhamzeh、Shabnam Shaabani、Mona Hamidzad Sangachin、Ahmad Shaabani

  DOI：10.1007/s11164-015-2181-4

  日期：2016.4

  Guanidinium-based sulfonic acid as a new Brønsted acid organocatalyst has been synthesized, characterized, and applied for the synthesis of 3,4-dihydroquinoxalin-2-amine, 1,6-dihydropyrazine-2,3-dicarbonitrile, triazolo[1,2-a]indazole-trione, and spiro triazolo[1,2-a]indazole-tetraone derivatives in an aqueous medium. The catalytic system, reported here, possesses the advantages of both homogeneous and heterogeneous catalysts and can be repetitively used in water.

  基于胍基磺酸作为一种新型布仑斯特酸有机催化剂已被合成、表征，并应用于水相中合成3,4-二氢喹唔啉-2-胺、1,6-二氢吡嗪-2,3-二腈、三唑并[1,2-a]吲哚三酮和螺三唑并[1,2-a]吲哚四酮衍生物。本文报道的催化体系兼具均相和非均相催化剂的优势，并且可在水中重复使用。
• A novel catalytic one-pot three-component reaction of aldehydes, o-phenylenediamine derivatives and isocyanides for synthesis of 3,4-dihydroquinoxalin-2-amine derivatives in the presence of zirconium tetrachloride
  作者：Seyed Ali Jehbez、Hamid Reza Safaei

  DOI：10.1007/s13738-018-1301-7

  日期：2018.5

  synthesis of biologically interesting 3,4-dihydroquinoxalin-2-amine derivatives through a three-component condensation reaction of o-phenylenediamines, carbonyl compounds and isocyanides in ethanol at room temperature is described. In this work, unlike the other methods, aldehydes reacted as well as ketones in the presence of 10 mol% of zirconium tetrachloride as catalyst to afford good to excellent yields

  摘要描述了一种简单有效的一锅法，用于在室温下通过邻苯二胺，羰基化合物和异氰化物在乙醇中的三组分缩合反应合成生物学上令人感兴趣的3,4-二氢喹喔啉-2-胺衍生物。在这项工作中，与其他方法不同，在10摩尔％的四氯化锆作为催化剂的存在下，醛类和酮类也发生了反应，从而提供了良好的产品收率。该方法由于其对环境有益的特性，高收率，易于处理以及对醛和酮的可靠性而具有重要的价值。通过IR，1 H NMR，13 C NMR和元素分析系统地表征了新合成的化合物。 图形概要醛，邻苯二胺衍生物和异氰酸酯的新型催化一锅三组分反应，用于在四氯化锆存在下合成3,4-二氢喹喔啉-2-胺衍生物 。
• Eco-friendly synthesis of 3,4-dihydroquinoxalin-2-amine, diazepine-tetrazole and benzodiazepine-2-carboxamide derivatives with the aid of MCM-48/H₅ PW₁₀ V₂ O₄₀
  作者：Esmail Vessally、Rahim Hosseinzadeh-Khanmiri、Ebrahim Ghorbani-Kalhor、Moosa Es'haghi、Ladan Ejlali

  DOI：10.1002/aoc.3729

  日期：2017.10

  efficient, eco‐friendly and highly recyclable catalyst for the one‐pot and multicomponent synthesis of 3,4‐dihydroquinoxalin‐2‐amine, diazepine‐tetrazole and benzodiazepine‐2‐carboxamide derivatives in aqueous media and at room temperature with high yields in short reaction times (40–60 min). The recoverable catalyst was easily recycled at least five times without any loss of catalytic activity. The

  生产了由MCM-48 / H 5 PW 10 V 2 O 40组成的非均质材料，并将其用作高效，生态友好且高度可回收的催化剂，用于3,4-二氢喹喔啉-2-胺的一锅多组分合成，二氮杂-四唑和苯并二氮杂-2-羧酰胺衍生物在水性介质中和室温下以高收率在较短的反应时间（40-60分钟）内产生。可回收的催化剂易于循环至少五次，而没有任何催化活性的损失。使用1 H NMR和13 C NMR光谱确认获得的产物的结构。
• Wool-SO3H and nano-Fe3O4@wool as two green and natural-based renewable catalysts in one-pot isocyanide-based multicomponent reactions
  作者：Ahmad Shaabani、Zeinab Hezarkhani、Mohammad Tayeb Faroghi

  DOI：10.1007/s00706-016-1717-7

  日期：2016.11

  Natural wool sulfonic acid (wool-SO3H) and wool-supported Fe3O4 nanoparticles (nano-Fe3O4@wool) with highly loaded Fe3O4 nanoparticles were simply synthesized and characterized by flame atomic absorption spectroscopy, X-ray diffraction, thermogravimetric analysis, and scanning electron microscopy. The successful synthesis of 3,4-dihydroquinoxalin-2-amine, 1,6-dihydropyrazine-2,3-dicarbonitrile, (cyanophenylamino)acetamide, tetrahydro-1H-1,5-benzodiazepine-2-carboxamide, and 4,5,6,7-tetrahydro-1H-1,4-diazepine-5-carboxamide derivatives shows that wool-SO3H and Fe3O4@wool nanocomposite have high catalytic activity and can be repetitively used as two biodegradable catalysts.
• Cellulose-SO3H as a biodegradable solid acid catalyzed one-pot three-component Ugi reaction: Synthesis of α-amino amide, 3,4-dihydroquinoxalin-2-amine, 4H-benzo[b][1,4]thiazin-2-amine and 1,6-dihydropyrazine-2,3-dicarbonitrile derivatives
  作者：Hamid Mofakham、Zeinab Hezarkhani、Ahmad Shaabani

  DOI：10.1016/j.molcata.2012.04.002

  日期：2012.8

  A variety of amines has become utilized in the three-compound Ugi reaction and synthesis of 3,4-dihydroquinoxalin-2-amine, 4H-benzo[b][1,4]thiazin-2-amine and 1,6-dihydropyrazine-2,3-dicarbonitrile derivatives in the presence of cellulose sulfuric acid as a biopolymer solid acid catalyst in ethanol at room temperature. (c) 2012 Elsevier B.V. All rights reserved.