N-tert-butyl-1'H-spiro[cyclohexane-1,2'-quinoxaline]-3'-amine | 953132-31-5

• 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-tert-butyl-1'H-spiro[cyclohexane-1,2'-quinoxaline]-3'-amine
• 英文别名: N-tert-butylspiro[1,4-dihydroquinoxaline-3,1'-cyclohexane]-2-imine
• CAS: 953132-31-5
• 化学式: C₁₇H₂₅N₃
• mdl: MFCD27214247
• 分子量: 271.406
• InChiKey: MEQPRAQDVWGHNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  异氰酸叔丁酯 、 环己酮 、 邻苯二胺 在 cerium(IV) oxide 作用下， 以 水 为溶剂， 反应 2.0h， 以89%的产率得到N-tert-butyl-1'H-spiro[cyclohexane-1,2'-quinoxaline]-3'-amine
  参考文献：
  名称：

  铈氧化物纳米颗粒催化三组分协议在水中高度取代的新颖喹喔啉-2-胺衍生物和3,4-二氢喹喔啉-2-胺的合成†

  摘要：

  使用CeO 2纳米颗粒催化1,2-二胺与醛和异氰酸酯的三组分反应，在水中进行了新的喹喔啉-2-胺衍生物的合成。通过1，2-二胺，酮和异氰酸酯之间的反应，还合成了多种3，4-二氢喹喔啉-2-胺衍生物。这种新方法为合成喹喔啉-2-胺和3,4-二氢喹喔啉-2-胺提供了一种对环境无害且有效的方法。

  DOI：

  10.1039/c4ra00717d

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。
• Rapid and Efficient One-Pot Synthesis of 3,4-Dihydroquinoxalin-2-Amine Derivatives Catalyzed by Co₃O₄@SiO₂ Core-Shell Nanoparticles Under Ultrasound Irradiation
  作者：Mohammad Ali Ghasemzadeh、Boshra Mirhosseini-Eshkevari、Mohammad Hossein Abdollahi-Basir

  DOI：10.2174/1386207319666160524141831

  日期：2016.7.12

  three-component reactions of ophenylenediamines (OPDA), diverse ketones and various isocyanides in ethanol under ultrasound irradiation. The combinatorial synthesis was attained for this procedure with applying ultrasound irradiation while making use of ethanol as green ambient. The present approach offers several advantages such as high yields, environmentally benign, simple work-up, excellent yield of products

  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。
• 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。
• 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.
• EDTA-catalyzed synthesis of 3,4-dihydroquinoxalin-2-amine derivatives by a three-component coupling of one-pot condensation reactions in an aqueous medium
  作者：Srinivasa Rao Kolla、Yong Rok Lee

  DOI：10.1016/j.tet.2010.09.050

  日期：2010.11

  This paper describes a simple and efficient one-pot synthetic approach for the preparation of biologically interesting 3,4-dihydroquinoxalin-2-amine derivatives using EDTA-catalyzed three-component reactions of o-phenylenediamines, carbonyl compounds, and isocyanides in an aqueous medium. This method is of great value because of its environmentally benign character, high yields, and ease of handling. (C) 2010 Elsevier Ltd. All rights reserved.