1-(p-tolylamino)pentan-3-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(p-tolylamino)pentan-3-one
• 英文别名: 1-(4-Methylanilino)pentan-3-one；1-(4-methylanilino)pentan-3-one
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: CZMRDQBHWHMJHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-戊烯-3-酮 、 乙烷,三氯氟- 在 1,1,3,3-tetramethylguanidinium lactate 作用下， 反应 0.5h， 以92%的产率得到1-(p-tolylamino)pentan-3-one
  参考文献：
  名称：

  基于胍的特定任务离子液体作为无溶剂条件下氮杂-迈克尔加成的催化剂

  摘要：

  建立了在无溶剂条件下使用[TMG] [Lac]作为催化剂，将脂肪族和芳香族胺类氮杂-迈克尔加成至缺电子烯烃的有效而简便的方法。

  DOI：

  10.1007/s11164-011-0296-9

文献信息

• Lithium tetrafluoroborate catalyzed highly efficient inter- and intramolecular aza-Michael addition with aromatic amines
  作者：U.P. Lad、M.A. Kulkarni、U.V. Desai、P.P. Wadgaonkar

  DOI：10.1016/j.crci.2011.09.006

  日期：2011.12

  Abstract Lithium tetrafluoroborate has been demonstrated for the first time to be an efficient catalyst in intermolecular aza-Michael addition aromatic amines to electron deficient alkenes. Suitability of the same catalyst in intramolecular aza-Michael addition leading 2-aryl-2,3-dihydroquinolin-4(1H) ones has also been described.

  摘要 四氟硼酸锂首次被证明是分子间氮杂-迈克尔加成芳香胺到缺电子烯烃的有效催化剂。也描述了相同催化剂在分子内氮杂-迈克尔加成引导 2-芳基-2,3-二氢喹啉-4(1H) 中的适用性。
• Highly efficient aza-Michael reactions of aromatic amines and N-heterocycles catalyzed by a basic ionic liquid under solvent-free conditions
  作者：Lei Yang、Li-Wen Xu、Wei Zhou、Lyi Li、Chun-Gu Xia

  DOI：10.1016/j.tetlet.2006.08.103

  日期：2006.10

  A task-specific basic ionic liquid, [Bmim]OH, has been introduced as a catalyst for the aza-Michael addition of aromatic amines and N-heterocycles to cyclic or acyclic ketones under neat conditions. The catalyst can be recycled for subsequent reactions without any appreciable loss of efficiency.

  已引入一种特定任务的碱性离子液体[Bmim] OH，作为在纯净条件下将芳族胺和N-杂环向氮杂-迈克尔加成至环状或无环酮的催化剂。催化剂可以再循环用于随后的反应，而没有任何明显的效率损失。
• Guanidine-based task-specific ionic liquids as catalysts for aza-Michael addition under solvent-free conditions
  作者：Anguo Ying、Ming Zheng、Haidan Xu、Fangli Qiu、Changhua Ge

  DOI：10.1007/s11164-011-0296-9

  日期：2011.10

  An efficient and facile protocol for aza-Michael addition of aliphatic and aromatic amines to electron-deficit alkenes using [TMG][Lac] as catalyst under solvent-free conditions was established.

  建立了在无溶剂条件下使用[TMG] [Lac]作为催化剂，将脂肪族和芳香族胺类氮杂-迈克尔加成至缺电子烯烃的有效而简便的方法。
• Green, efficient and practical Michael addition of arylamines to α,β-unsaturated ketones
  作者：Ran Jiang、Dan-Hua Li、Jing Jiang、Xiao-Ping Xu、Tao Chen、Shun-Jun Ji

  DOI：10.1016/j.tet.2011.03.082

  日期：2011.5

  The aza-Michael addition of aromatic amines to alpha,beta-unsaturated ketones was carried out effectively at room temperature in good to excellent yields without any catalyst or solvent. It was significant that part of adducts could be collected in almost quantitative yield without column chromatography. This procedure offered a green, efficient, and practical approach for the synthesis of beta-amino ketones. (C) 2011 Elsevier Ltd. All rights reserved.
• An environmentally benign protocol: catalyst-free Michael addition of aromatic amines to α,β-unsaturated ketones in glycerol
  作者：Anguo Ying、Qunhui Zhang、Hongmin Li、Gangfeng Shen、Weizhong Gong、Mingju He

  DOI：10.1007/s11164-012-0575-0

  日期：2013.2

  Glycerol was used as a reaction medium as well as promoter for aza-Michael addition of aromatic amines to electronic deficient α,β-unsaturated ketones. Various aromatic amines can react smoothly with chalcone, 2-cyclohexen-1-one, 2-cyclopenten-1-one, and ethyl vinyl ketone to achieve good to excellent yields in the absence of any catalyst.

  甘油被用作反应介质，同时也是芳香胺与缺电子的α,β-不饱和酮的aza-Michael加成反应的促进剂。多种芳香胺能够顺利地与查尔酮、2-环己烯-1-酮、2-环戊烯-1-酮和乙基乙烯酮反应，在无需任何催化剂的情况下实现优良至极佳的产率。