1-(2-ethyl-3-methylquinolin-6-yl)ethanone | 309754-11-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(2-ethyl-3-methylquinolin-6-yl)ethanone
• 英文别名: 2-ethyl-6-acetyl-3-methylquinoline；6-acetyl-2-ethyl-3-methylquinoline；1-(2-ethyl-3-methyl-[6]quinolyl)-ethanone；1-(2-Aethyl-3-methyl-[6]chinolyl)-aethanon
• CAS: 309754-11-8
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: HVPZQGNEVFHRRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三正丙胺 、 1-(2-ethyl-3-methylquinolin-6-yl)ethanone 在 ruthenium trichloride 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 40.0h， 以51%的产率得到1-(2-ethyl-3-methylquinolin-6-yl)pentan-1-one
  参考文献：
  名称：

  Ruthenium-Catalyzed Regioselectiveα-Alkylation of Ketones: The First Alkyl-Group Transfer from Trialkylamines to theα-C Atom of Ketones

  摘要：

  A new reaction: A ruthenium-catalyzed transfer of an alkyl group from a trialkylamine to the α-carbon atom of a ketone leads in good yields to α-alkylated ketones [Eq. (1)]. The reaction is applicable to a wide range of alkyl(alkyl), alkyl(aryl), and cyclic ketones, and in the case of unsymmetrical ketones it takes place regioselectively at the less hindered α-position.

  DOI：

  10.1002/1521-3773(20010302)40:5<958::aid-anie958>3.0.co;2-4
• 作为产物：
  描述：

  4-乙基苯胺 在 盐酸 、 potassium dichromate 、 硫酸 、 水 、 zinc(II) chloride 作用下， 生成 1-(2-ethyl-3-methylquinolin-6-yl)ethanone
  参考文献：
  名称：

  The Nitrogen Compounds in Petroleum Distillates. XX. Isolation of 2-Methyl-8-ethylquinoline from California Petroleum and Proof of Structure through Degradation and Synthesis

  摘要：

  DOI：

  10.1021/ja01848a002

文献信息

• Titania-Supported Iridium Subnanoclusters as an Efficient Heterogeneous Catalyst for Direct Synthesis of Quinolines from Nitroarenes and Aliphatic Alcohols
  作者：Lin He、Jian-Qiang Wang、Ya Gong、Yong-Mei Liu、Yong Cao、He-Yong He、Kang-Nian Fan

  DOI：10.1002/anie.201104089

  日期：2011.10.17

  A versatile heterogeneous catalyst consisting of sub‐nanosized iridium clusters deposited on titania (Ir/TiO2‐NCs) promotes the direct tandem synthesis of quinoline derivatives from readily available nitroarenes and aliphatic alcohols under mild and additive‐free conditions (see scheme). The process tolerates the presence of various reactive functional groups and is highly selective.

  一种通用的多相催化剂，由沉积在二氧化钛上的亚纳米级铱簇（Ir / TiO 2 -NCs）组成，可促进在温和且无添加剂的条件下，由易得的硝基芳烃和脂肪族醇直接串联合成喹啉衍生物。该方法可耐受各种反应性官能团的存在，并且具有很高的选择性。
• Ruthenium-catalyzed formal alkyl group transfer: Synthesis of quinolines from nitroarenes and alkylammonium halides
  作者：Chan Sik Cho、Na Young Lee、Tae-Jeong Kim、Sang Chul Shim

  DOI：10.1002/jhet.5570410320

  日期：2004.5

  Nitroarenes are reductively cyclized with an array of tetraalkylammonium halides and trialkylarnmonium chlorides in the presence of a catalytic amount of a ruthenium catalyst along with tin(II) chloride dihydrate at 180° to afford the corresponding quinolines in moderate to good yields. The addition of tin(II) chloride dihydrate is necessary for the effective formation of quinolines and toluene is

  在催化量的钌催化剂和二水合氯化锡（II）的存在下，将四烷基卤化铵和三烷基氯化铵与硝基芳烃进行还原性环合，在180°下产生适量至良好收率的相应喹啉。为了有效形成喹啉，必须添加二水合氯化锡（II），甲苯是选择的溶剂。针对该催化过程，提出了一种反应途径，该反应途径包括首先将硝基芳烃还原为苯胺，然后将烷基铵卤化物转化为烷基胺，将烷基从烷基胺转移至苯胺以形成亚胺，使亚胺二聚，并进行杂环化。
• Ruthenium-Catalyzed Synthesis of Quinolines from Anilines and Allylammonium Chlorides in an Aqueous Medium via Amine Exchange Reaction
  作者：Chan Sik Cho、Joon Seok Kim、Byoung Ho Oh、Tae-Jeong Kim、Sang Chul Shim、Nam Sik Yoon

  DOI：10.1016/s0040-4020(00)00694-3

  日期：2000.9

  Anilines react with allylammonium chlorides in an aqueous medium (H2O–dioxane) in the presence of a catalytic amount of RuCl2(PPh3)3 together with SnCl2·2H2O to give the corresponding quinolines in moderate to good yields. The existence of SnCl2·2H2O is necessary for the effective formation of quinolines, and a reaction pathway involving amine exchange reaction between anilines and allylammonium chlorides

  在催化量的RuCl 2（PPh 3）3和SnCl 2 ·2H 2 O的存在下，苯胺在水性介质（H 2 O-二恶烷）中与烯丙基氯化铵反应，以中等至良好的收率得到相应的喹啉。SnCl 2 ·2H 2 O的存在对于喹啉的有效形成是必需的，并且针对该催化过程提出了涉及苯胺和烯丙基氯化铵之间形成亚胺的胺交换反应的反应路径。
• Ruthenium-Catalyzed Regioselectiveα-Alkylation of Ketones: The First Alkyl-Group Transfer from Trialkylamines to theα-C Atom of Ketones
  作者：Chan Sik Cho、Bok Tae Kim、Myung Jin Lee、Tae-Jeong Kim、Sang Chul Shim

  DOI：10.1002/1521-3773(20010302)40:5<958::aid-anie958>3.0.co;2-4

  日期：2001.3.2

  A new reaction: A ruthenium-catalyzed transfer of an alkyl group from a trialkylamine to the α-carbon atom of a ketone leads in good yields to α-alkylated ketones [Eq. (1)]. The reaction is applicable to a wide range of alkyl(alkyl), alkyl(aryl), and cyclic ketones, and in the case of unsymmetrical ketones it takes place regioselectively at the less hindered α-position.
• The Nitrogen Compounds in Petroleum Distillates. XX. Isolation of 2-Methyl-8-ethylquinoline from California Petroleum and Proof of Structure through Degradation and Synthesis
  作者：Richard A. Glenn、J. R. Bailey

  DOI：10.1021/ja01848a002

  日期：1941.3