3-[(2-methylphenyl) amino]-1,3-diphenylpropan-1-one | 191793-92-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-[(2-methylphenyl) amino]-1,3-diphenylpropan-1-one
• 英文别名: 3-(2-Methylanilino)-1,3-diphenylpropan-1-one；3-(2-methylanilino)-1,3-diphenylpropan-1-one
• CAS: 191793-92-7
• 化学式: C₂₂H₂₁NO
• 分子量: 315.415
• InChiKey: CJLFEKDNADDKPE-UHFFFAOYSA-N

物化性质

• 熔点：
  102-103 °C
• 沸点：
  510.0±45.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[(2-methylphenyl) amino]-1,3-diphenylpropan-1-one 在 Chiralcel OJ 作用下， 以 异丙醇 为溶剂， 生成 3-[(2-methylphenyl) amino]-1,3-diphenylpropan-1-one 、 3-[(2-methylphenyl) amino]-1,3-diphenylpropan-1-one
  参考文献：
  名称：

  各种基于多糖的手性固定相的HPLC手性分离β-氨基酮的筛选方法

  摘要：

  当苯甲醛与一些伯胺和苯乙酮缩合时，通过Mannich反应合成了九种β-氨基酮。通过使用光谱法鉴定纯化的化合物。这些衍生物的对映体分离采用几种涂覆并固定多糖固定相，即，CHIRALCEL通过高效液相色谱法（HPLC）进行® OD-H，CHIRALCEL ® OD，CHIRALCEL ® OJ，CHIRALPAK ® AD，CHIRALPAK ® IA和CHIRALPAK ® IB使用组成不同的流动相ñ正己烷和乙醇按各种比例混合，或纯乙醇或异丙醇。在等度正相模式下检查了这些手性固定相的保留行为和选择性。结果表明，纤维素衍生物在分离外消旋β-氨基酮方面比直链淀粉衍生物具有更高的对映选择性。手性27：332–338，2015年。 ©2015 Wiley Periodicals，Inc.

  DOI：

  10.1002/chir.22434
• 作为产物：
  描述：

  苯亚甲基苯乙酮 、 邻甲苯胺 反应 6.0h， 以66%的产率得到3-[(2-methylphenyl) amino]-1,3-diphenylpropan-1-one
  参考文献：
  名称：

  Supramolecular Assemblies in Ionic Liquid Catalysis for Aza-Michael Reaction

  摘要：

  Supramolecular assemblies formed by a relay of cooperative hydrogen bonds and charge charge interactions have been identified/characterized by (+ve) ESI and MALDI-TOF-TOF MS and MS-MS studies during the aza-Michael reaction of amines with alpha,beta-unsaturated carbonyl compounds in the presence of ionic liquids (ILs) digging out the role of catalysis by ILs, forming the basis of rational design/selection as organocatalysts, and offering a diagnostic model to predict/rationalize the selectivity of the aza-Michael reaction in a competitive environment.

  DOI：

  10.1021/ol101557t

文献信息

• H3PW12O40 supported on silica-encapsulated γ-Fe2O3 nanoparticles: a novel magnetically-recoverable catalyst for three-component Mannich-type reactions in water
  作者：Ezzat Rafiee、Sara Eavani

  DOI：10.1039/c1gc15291b

  日期：——

  A new type of magnetically-recoverable catalyst was synthesized by the immobilization of H3PW12O40 on the surface of silica-encapsulated γ-Fe2O3 nanoparticles. This catalyst was characterized by transmission electron microscopy (TEM), a laser particle size analyzer, infrared spectroscopy (IR) and inductively coupled plasma atomic emission spectroscopy (ICP-AES). The results show that the particles are mostly spherical in shape and have an average size of approximately 94 nm. The characterization data derived from IR spectroscopy reveal that H3PW12O40 on the support exists in the Keggin structure. The acidity of the catalyst was measured by a potentiometric titration with n-butylamine. To our surprise, this very strong solid acid catalyst showed an excellent distribution of acid sites, suggesting that the catalyst possesses a higher number of surface active sites compared to its homogeneous analogues. The activity of the catalyst was probed through one-pot three-component Mannich-type reactions of aldehydes, amines and ketones in water at room temperature. The excellent conversions show that the catalyst has strong and sufficient acidic sites, which are responsible for its catalytic performance. After the reaction, the catalyst/product separation could be easily achieved with an external magnetic field, and more than 95% of the catalyst could usually be recovered. The catalyst was reused at least five times without any loss of its high catalytic activity.

  通过将H3PW12O40固定在二氧化硅包覆的γ-Fe2O3纳米颗粒表面，合成了一种新型磁性可回收催化剂。该催化剂通过透射电子显微镜（TEM）、激光粒度分析仪、红外光谱（IR）和电感耦合等离子体原子发射光谱（ICP-AES）进行了表征。结果显示，颗粒主要呈球形，平均尺寸约为94纳米。红外光谱表征数据揭示，负载上的H3PW12O40以Keggin结构存在。催化剂的酸度通过用正丁胺进行的电位滴定法测量。令人惊讶的是，这种非常强的固体酸催化剂显示出优异的酸位点分布，表明催化剂相对于均相类似物具有更高的表面活性位点数量。催化剂的活性通过在水中的室温下进行的一锅法三组分Mannich型反应，即醛、胺和酮的反应来评估。优异的转化率表明，催化剂具有强烈且充分的酸性位点，这是其催化性能的原因。反应后，通过外部磁场可以轻松实现催化剂/产物分离，通常可以回收超过95%的催化剂。该催化剂至少可以重复使用五次，而不会损失其高催化活性。
• Cellulose-Supported Ionic Liquid Phase Catalyst-Mediated Mannich Reaction
  作者：Sharanabasappa Khanapure、Megha Jagadale、Dolly Kale、Shivanand Gajare、Gajanan Rashinkar

  DOI：10.1071/ch18576

  日期：——

  Cellulose-supported ionic liquid phase (SILP) catalyst containing a camphor sulfonate anion with a pendant ferrocenyl group was prepared and characterised with different analytical techniques such as Fourier-transform infrared, Fourier-transform Raman, and cross polarization–magic angle spinning (CP-MAS) 13C NMR spectroscopy, X-ray diffraction, scanning electron microscopy, and thermogravimetric analysis

  制备了带有樟脑烯基侧基的樟脑磺酸根阴离子的纤维素负载离子液相催化剂，并采用不同的分析技术进行了表征，如傅立叶变换红外光谱，傅立叶变换拉曼光谱和交叉极化-魔角纺丝（CP- MAS）13 C NMR光谱，X射线衍射，扫描电子显微镜和热重分析。SILP催化剂在通过曼尼希反应合成β-氨基羰基化合物中显示出优异的催化活性。回收研究表明，SILP催化剂可以重复使用六次，而催化活性不会显着降低。
• Aluminized Polyborate: A New and Eco-friendly Catalyst for One-pot Multicomponent Synthesis of 1,3-Diaryl-3-(arylamino)propan-1-ones <i>via</i> Mannich Reaction
  作者：Anil S. Mali、Prerna Ganwir、Ganesh U. Chaturbhuj

  DOI：10.1080/00304948.2022.2057141

  日期：2022.7.4

  Published in Organic Preparations and Procedures International: The New Journal for Organic Synthesis (Vol. 54, No. 4, 2022)

  （2022 年）。镀铝聚硼酸盐：一种新型环保催化剂，用于通过曼尼希反应一锅法合成 1,3-二芳基-3-(芳氨基)丙-1-酮。国际有机制剂和程序。领先于印刷。
• Screening Approach for Chiral Separation of β-Aminoketones by HPLC on Various Polysaccharide-Based Chiral Stationary Phases
  作者：Khadidja Addadi、Khaled Sekkoum、Nasser Belboukhari、Abdelkrim Cheriti、Hassan Y. Aboul-Enein

  DOI：10.1002/chir.22434

  日期：2015.5

  Nine β‐aminoketones were synthesized via Mannich reaction when benzaldehyde was condensed with some primary amines and acetophenone. The purified compounds were identified by using spectroscopic methods. The enantiomeric separation of these derivatives was carried out by high‐performance liquid chromatography (HPLC) using several coated and immobilized polysaccharide stationary phases, namely, Chiralcel®

  当苯甲醛与一些伯胺和苯乙酮缩合时，通过Mannich反应合成了九种β-氨基酮。通过使用光谱法鉴定纯化的化合物。这些衍生物的对映体分离采用几种涂覆并固定多糖固定相，即，CHIRALCEL通过高效液相色谱法（HPLC）进行® OD-H，CHIRALCEL ® OD，CHIRALCEL ® OJ，CHIRALPAK ® AD，CHIRALPAK ® IA和CHIRALPAK ® IB使用组成不同的流动相ñ正己烷和乙醇按各种比例混合，或纯乙醇或异丙醇。在等度正相模式下检查了这些手性固定相的保留行为和选择性。结果表明，纤维素衍生物在分离外消旋β-氨基酮方面比直链淀粉衍生物具有更高的对映选择性。手性27：332–338，2015年。 ©2015 Wiley Periodicals，Inc.
• Supramolecular Assemblies in Ionic Liquid Catalysis for Aza-Michael Reaction
  作者：Sudipta Raha Roy、Asit K. Chakraborti

  DOI：10.1021/ol101557t

  日期：2010.9.3

  Supramolecular assemblies formed by a relay of cooperative hydrogen bonds and charge charge interactions have been identified/characterized by (+ve) ESI and MALDI-TOF-TOF MS and MS-MS studies during the aza-Michael reaction of amines with alpha,beta-unsaturated carbonyl compounds in the presence of ionic liquids (ILs) digging out the role of catalysis by ILs, forming the basis of rational design/selection as organocatalysts, and offering a diagnostic model to predict/rationalize the selectivity of the aza-Michael reaction in a competitive environment.