4-(4-methoxyphenylamino)-4-(phenyl)butan-2-one | 21086-06-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-methoxyphenylamino)-4-(phenyl)butan-2-one
• 英文别名: 4-(4-methoxyphenylamino)-4-phenylbutan-2-one；4-phenyl-4-(phenylamino)butan-2-one；4-(4-Methoxyanilino)-4-phenylbutan-2-one
• CAS: 21086-06-6
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: VZLMGXYCEJCIGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲氧苯胺 、 苄叉丙酮 在 magnesia 作用下， 反应 3.17h， 以88%的产率得到4-(4-methoxyphenylamino)-4-(phenyl)butan-2-one
  参考文献：
  名称：

  MgO nanoparticles as an efficient and reusable catalyst for aza-Michael reaction

  摘要：

  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。

  DOI：

  10.1007/s13738-013-0338-x

文献信息

• Squaric acid as an impressive organocatalyst for Michael addition in water
  作者：Najmadin Azizi、Elham Saki、Mahtab Edrisi

  DOI：10.1016/j.crci.2011.07.003

  日期：2011.11

  Résumé A simple, green, and environmentally benign protocol for squaric acid (5 mg) catalyst conjugate addition of aromatic amines and thiols to unsaturated carbonyl compounds in water in good to excellent yields is developed. The advantages of low sensitivity toward moisture and oxygen, high tolerance of different functional groups, green reaction media and efficient recyclability make this organocatalyst suitable for both laboratory and industrial scale synthesis of β-substituted carbonyls under very mild conditions.

  简历 开发了一种简单、绿色且对环境友好的方案，利用胡椒酸（5毫克）作为催化剂，在水介质中实现了芳香胺和硫醇对不饱和羰基化合物的共轭加成反应，产率良好至优异。该有机催化剂具有对湿气和氧气低敏感性、对多种官能团高度耐受性、绿色反应介质及高效可回收性等优点，非常适用于在非常温和条件下进行β-取代羰基化合物的实验室及工业规模合成。
• Lanthanide Triflate Catalyzed Imino Diels-Alder Reactions; Convenient Syntheses of Pyridine and Quinoline Derivatives
  作者：Shū Kobayashi、Haruro Ishitani、Satoshi Nagayama

  DOI：10.1055/s-1995-4066

  日期：1995.9

  Lanthanide triflate catalyzed imino Diels-Alder reactions of imines with dienes or alkenes have been developed. A new group of Lewis acids, lanthanide triflates, are quite effective for the catalytic activation of imines. Unique reactivities of imines which work as both dienophiles and azadienes under certain conditions have been revealed. Three-component coupling reactions between aldehydes, amines, and dienes or alkenes were successfully carried out by using lanthanide triflate as a catalyst to afford pyridine and quinoline derivatives in high yields. The Lewis acid catalysts were stable and kept their activity even in the presence of water and amines. A stepwise reaction mechanism for these reactions is suggested from the experimental results.

  已开发了铈三氟甲磺酸盐催化的亚胺与二烯或烯烃的亚胺Diels-Alder反应。新一类路易斯酸，即铈三氟甲磺酸盐，在催化亚胺的活化方面非常有效。已揭示出亚胺在某些条件下同时作为二烯亲和体和氮烯体的独特反应性。通过使用铈三氟甲磺酸盐作为催化剂，成功进行了醛、胺与二烯或烯烃之间的三组分偶联反应，得到高产率的吡啶和喹啉衍生物。这些路易斯酸催化剂在水和胺存在的情况下依然保持稳定性和活性。根据实验结果，提出了这些反应的逐步反应机理。
• Ln(OTf)₃- or Sc(OTf)₃-Catalyzed Three Components Coupling Reactions between Aldehydes, Amines, and Dienes or Alkenes. Efficient Syntheses of Pyridine and Quinoline Derivatives
  作者：Shu Kobayashi、Haruro Ishitani、Satoshi Nagayama

  DOI：10.1246/cl.1995.423

  日期：1995.6

  Three components coupling reactions between aldehydes, amines, and dienes or alkenes were catalyzed by lanthanide or scandium triflate to afford pyridine and quinoline derivatives in high yields. The Lewis acid catalysts were stable and kept their activity even in the presence of water and amines.

  在镧系元素或三氟甲磺酸钪的催化下，醛、胺和二烯或烯烃之间的三组分偶联反应以高产率得到吡啶和喹啉衍生物。即使在水和胺的存在下，路易斯酸催化剂也很稳定并保持其活性。
• A novel Mannich-type reaction in aqueous media. Lanthanide triflate-catalysed condensation of aldehydes, amines and vinyl ethers for the synthesis of β-amino ketones
  作者：Shū Kobayashi、Haruro Ishitani

  DOI：10.1039/c39950001379

  日期：——

  A novel Mannich-type reaction between an aldehyde, an amine and a vinyl ether is catalysed by lanthanide triflates to afford a β-amino ketone in good yield in aqueous media.

  一种新型的曼尼希型反应，涉及醛、胺和乙烯基醚，在三氟甲磺酸镧系元素催化下，在水中以良好产率生成β-氨基酮。
• Heteropoly acid in ionic liquid — An efficient and recyclable system for one-pot three-component Mannich reaction
  作者：Meghana S Rasalkar、Sachin V Bhilare、Amol R Deorukhkar、Nitin B Darvatkar、Manikrao M Salunkhe

  DOI：10.1139/v06-176

  日期：2007.1.1

  This paper describes a one-pot three-component Mannich reaction, catalyzed by phosphotungstic acid (H3PW12O40), a heteropoly acid in ionic liquid. The catalyst was found to be mild and efficient, and the protocol affords β-amino ketones in good yields under ambient conditions. Several ionic liquids and conventional organic solvents were employed for the reaction. The ionic liquid 1-butyl-3-methylimidazolium

  本文描述了一种由离子液体中的杂多酸磷钨酸 (H3PW12O40) 催化的一锅三组分曼尼希反应。发现该催化剂温和且高效，并且该方案在环境条件下以良好的产率提供 β-氨基酮。该反应使用了几种离子液体和常规有机溶剂。离子液体 1-丁基-3-甲基咪唑鎓四氟硼酸盐 ([bmim]BF4) 在产物产率方面提供了最好的结果。观察到均相反应介质有利于反应的产率。关键词：曼尼希反应，β-氨基酮，磷钨酸，离子液体，可回收性。