2-isobutyl-1,2,3,4-tetrahydroquinoxaline | 1327154-09-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-isobutyl-1,2,3,4-tetrahydroquinoxaline
• 英文别名: 2-(2-Methylpropyl)-1,2,3,4-tetrahydroquinoxaline；2-(2-methylpropyl)-1,2,3,4-tetrahydroquinoxaline
• CAS: 1327154-09-5
• 化学式: C₁₂H₁₈N₂
• 分子量: 190.288
• InChiKey: KOUOWTOAWJUDNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(异丁基)喹喔啉 在 2,2'-联吡啶 、 甲酸 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 sodium formate 作用下， 以 水 为溶剂， 反应 9.0h， 以97%的产率得到2-isobutyl-1,2,3,4-tetrahydroquinoxaline
  参考文献：
  名称：

  用于水中N-杂环转移加氢的多功能（五甲基环戊二烯基）铑-2,2'-联吡啶（Cp * Rh-bpy）催化剂

  摘要：

  采用由（五甲基环戊二烯基）二氯化铑二聚体[Cp * RhCl 2 ] 2组成的催化体系的研究报道了在水溶液中以甲酸为氢源，将2,2'-联吡啶（bpy）用于转移各种喹喔啉，喹喔啉酮，喹啉和吲哚的氢化反应。该方法以良好或优异的产率提供了各种四氢喹喔啉，二氢喹喔啉，四氢喹啉和二氢吲哚。催化剂对喹喔啉和喹喔啉酮的活性极好，底物与催化剂之比（S / C）为10000是可行的。配体的选择对于催化至关重要，并且水相还原显示出高度的pH依赖性，而酸性pH值则需要最佳还原。催化剂易于获得，并且反应在不需要惰性气氛的情况下操作简单。

  DOI：

  10.1002/adsc.201500491

文献信息

• Metal-free tandem cyclization/hydrosilylation to construct tetrahydroquinoxalines
  作者：Yixiao Pan、Changjun Chen、Xin Xu、Haoqiang Zhao、Jiahong Han、Huanrong Li、Lijin Xu、Qinghua Fan、Jianliang Xiao

  DOI：10.1039/c7gc03095a

  日期：——

  B(C₆F₅)₃-Catalyzed tandem cyclization/hydrosilylation for the step-economical construction of 1,2,3,4-tetrahydroquinoxalines from readily available starting materials has been developed.

  B(C6F5)3催化的串联环化/氢硅烷化反应，可从易得的起始物构建1,2,3,4-四氢喹啉。
• PROCESS FOR PRODUCING OPTICALLY ACTIVE AMINE
  申请人：TAKASAGO INTERNATIONAL CORPORATION

  公开号：US20150210657A1

  公开（公告）日：2015-07-30

  A process for producing an optically active amine compound, characterized by asymmetrically hydrogenating a prochiral carbon-nitrogen double bond in the presence of a ruthenium complex represented by general formula (1) or (2) (wherein P represents an optically active diphosphine, X represents an anionic group, and Ar represents an optionally substituted arylene group).

  一种制备光学活性胺化合物的方法，其特征在于在存在由通用式（1）或（2）表示的钌配合物的情况下，对一个丙半胱氨基双键进行不对称氢化（其中P代表光学活性二膦，X代表阴离子基团，Ar代表可选择取代的芳基基团）。
• Tetrabutylammonium Bromide-Catalyzed Transfer Hydrogenation of Quinoxaline with HBpin as a Hydrogen Source
  作者：Qi Guo、Jingchao Chen、Guoli Shen、Guangfu Lu、Xuemei Yang、Yan Tang、Yuanbin Zhu、Shiyuan Wu、Baomin Fan

  DOI：10.1021/acs.joc.1c02537

  日期：2022.1.7

  A metal-free environmentally benign, simple, and efficient transfer hydrogenation process of quinoxaline has been developed using the HBpin reagent as a hydrogen source. This reaction is compatible with a variety of quinoxalines offering the desired tetrahydroquinoxalines in moderate-to-excellent yields with Bu4NBr as a noncorrosive and low-cost catalyst.

  以HBpin试剂为氢源，开发了一种环境友好、简单、高效的喹喔啉转移加氢工艺。该反应与多种喹喔啉相容，以中等至优异的收率提供所需的四氢喹喔啉，Bu 4 NBr 作为非腐蚀性和低成本的催化剂。
• Rhodium-catalyzed transfer hydrogenation of quinoxalines with water as a hydrogen source
  作者：Xia Zhang、Jingchao Chen、Ruhima Khan、Guoli Shen、Zhenxiu He、Yongyun Zhou、Baomin Fan

  DOI：10.1039/c9ob02095k

  日期：——

  Rhodium-catalyzed transfer hydrogenation of quinoxalines with water as a hydrogen source was reported. The reaction allowed the simple preparation of tetrahydroquinoxalines under mild conditions. The deuterium-labelling experiment confirmed that water is the sole hydrogen source in the transfer hydrogenation reaction.

  据报道铑以水为氢源催化喹喔啉的转移加氢。该反应允许在温和的条件下简单地制备四氢喹喔啉。氘标记实验证实水是转移氢化反应中唯一的氢源。
• pH-Regulated transfer hydrogenation of quinoxalines with a Cp*Ir–diamine catalyst in aqueous media
  作者：Jing Tan、Weijun Tang、Yawei Sun、Zhen Jiang、Fei Chen、Lijin Xu、Qinghua Fan、Jianliang Xiao

  DOI：10.1016/j.tet.2011.06.067

  日期：2011.8

  The combination of [Cp*IrCl2](2) with N-(2-aminoethyl)-4-(trifluoromethyl)benzenesulfonamide constitutes an efficient catalyst for selective transfer hydrogenation of a variety of quinoxalines in water with HCOONa as the hydrogen source, affording the corresponding tetrahydroquinoxalines in good to excellent yields. The catalyst is air-stable, and the reduction could be performed without nitrogen protection. The aqueous phase reduction is shown to be highly pH-dependent, with acidic pH leading to better results. There exits a pH window for optimum rate, and the use of HOAc/NaOAc buffer solution is essential for maintaining a stable pH during the reaction. (C) 2011 Elsevier Ltd. All rights reserved.