3-(4-methylphenyl)aminocyclohexan-1-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: 3-(4-methylphenyl)aminocyclohexan-1-one
• 英文别名: 3-(4-Methylanilino)cyclohexan-1-one
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: OBRAIURXZOLTDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  2-环己烯-1-酮 、 乙烷,三氯氟- 以 甘油 为溶剂， 反应 24.0h， 以92%的产率得到3-(4-methylphenyl)aminocyclohexan-1-one
  参考文献：
  名称：

  An environmentally benign protocol: catalyst-free Michael addition of aromatic amines to α,β-unsaturated ketones in glycerol

  摘要：

  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。

  DOI：

  10.1007/s11164-012-0575-0

文献信息

• Triethylammonium acetate (TEAA): a recyclable inexpensive ionic liquid promotes the chemoselective aza- and thia-Michael reactions
  作者：Akhilesh K. Verma、Pankaj Attri、Varun Chopra、Rakesh K. Tiwari、Ramesh Chandra

  DOI：10.1007/s00706-008-0886-4

  日期：2008.9

  A new, highly efficient, inexpensive, recyclable, mild, convenient, and green protocol for chemoselective aza/thia- Michael addition reactions of amines/thiols to α,β - unsaturated compounds using triethylammonium acetate ( TEAA ) ionic liquid was developed. The catalyst can be recycled ten times and obviate the need for toxic and expensive catalysts.

  用于化学选择性氮杂/硫杂一种新的，高效率的，廉价的，可回收，轻度，方便，和绿色协议 迈克尔 的胺/硫醇到α，β加成反应 - 使用三乙基乙酸铵（不饱和化合物 TEAA ）离子液体被开发。该催化剂可以循环使用十次，从而消除了对有毒和昂贵催化剂的需求。
• MgO nanoparticles as an efficient and reusable catalyst for aza-Michael reaction
  作者：Mahmood Tajbakhsh、Maryam Farhang、Ali Asghar Hosseini

  DOI：10.1007/s13738-013-0338-x

  日期：2014.6

  MgO nanoparticles were prepared by an improved sol–gel technique which appeared to have narrow size distributions. The synthesized magnesium oxide nanoparticles were used as an efficient catalyst in aza-Michael reaction for addition of amines to a series of α,β-unsaturated carbonyl compounds and nitro olefins under solvent-free conditions at room temperature to afford high yields of the β-amino carbonyl and β-nitro amines. The catalyst can be recovered and reused at least five successive runs without loss of activity.

  通过改进的溶胶-凝胶技术制备的MgO纳米颗粒具有较窄的粒径分布。合成的氧化镁纳米颗粒在无溶剂条件下于室温下作为高效催化剂，用于一系列α,β-不饱和羰基化合物和硝基烯烃的氮迈克尔加成反应中，以及胺的加成反应，从而获得高产率的β-氨基羰基和β-硝基胺。该催化剂可回收并在至少五次连续运行中重复使用而不会损失活性。
• 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。
• 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。