t-butyl 6-chloro-2-methylquinoline-3-carboxylate | 1431472-22-8

• 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: t-butyl 6-chloro-2-methylquinoline-3-carboxylate
• 英文别名: tert-butyl 6-chloro-2-methylquinoline-3-carboxylate
• CAS: 1431472-22-8
• 化学式: C₁₅H₁₆ClNO₂
• 分子量: 277.751
• InChiKey: IGRXQYCMYNZFQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酰乙酸叔丁酯 、 2-氨基-5-氯苯甲醛 在 lithium trifluoromethanesulfonate 作用下， 以 neat (no solvent) 为溶剂， 生成 t-butyl 6-chloro-2-methylquinoline-3-carboxylate
  参考文献：
  名称：

  Lithium triflate (LiOTf): a highly efficient and reusable catalytic system for the synthesis of diversified quinolines under neat conditions

  摘要：

  A series of diverse polyfunctionalized quinolines were easily prepared in excellent yields via a Friedlander reaction of o-aminoaryl ketone or o-aminoaryl aldehyde with alpha-methylene ketones using lithium triflate as an expeditious catalyst under solvent free conditions. The protocol provides a practical and straightforward approach toward highly functionalized quinoline derivatives in excellent yields. The catalyst is easily recoverable and less sensitive to moisture, which makes this protocol more advantageous.

  DOI：

  10.1007/s00706-012-0906-2

文献信息

• Developing strategies for the preparation of Co-carbon catalysts involved in the free solvent selective synthesis of aza-heterocycles
  作者：M. Godino-Ojer、R.M. Martín-Aranda、F.J. Maldonado-Hódar、A.F. Pérez-Cadenas、E. Pérez-Mayoral

  DOI：10.1016/j.mcat.2017.11.037

  日期：2018.2

  We report herein different series of new zero valent Cobalt nanocarbons, as doped and supported aerogels, able to efficiently catalyze the reaction of 2-amino-5-chlorobenzaldehyde and beta-ketoesters, via Friedlander reaction. The reaction works under solvent-free and mild conditions affording yields over 80% in only 30 min of reaction time. The catalysts could be reused almost during two consecutive cycles without almost any activity loss. A comparative study between supported and doped-carbon aerogels, as catalysts highly efficient in the reaction, has allowed to stablish the relationship between the catalyst structure and the catalytic performance. At this regard, different parameters such as carbonization temperature and surface chemistry on the aerogels under study have been also explored. As a result, although the carbon matrix is involved in the reaction, the Co(0) nanoparticles on the carbon surface are the predominant active catalytic species. Oxygen functionalities on the oxidized samples in the surroundings of Co(0) nanoparticles probably prevent the access of the reagents, notably decreasing their catalytic performance. (C) 2017 Elsevier B.V. All rights reserved.