3-(2-methoxyphenyl)-1-phenyl-3-(N-phenylamino)propan-1-one | 37904-88-4

• 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-methoxyphenyl)-1-phenyl-3-(N-phenylamino)propan-1-one
• 英文别名: 3-(2-methoxyphenyl)-1-phenyl-3-(phenylamino)propan-1-one；3-anilino-3-(2-methoxyphenyl)-1-phenyl-1-propanone
• CAS: 37904-88-4
• 化学式: C₂₂H₂₁NO₂
• 分子量: 331.414
• InChiKey: JXUKMDCVTWOJRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-methoxychalcone 、 苯胺 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 3-(2-methoxyphenyl)-1-phenyl-3-(N-phenylamino)propan-1-one
  参考文献：
  名称：

  Silicon-Based Lewis Acid Assisted Cinchona Alkaloid Catalysis: Highly Enantioselective Aza-Michael Reaction under Solvent-Free Conditions

  摘要：

  The study showed that a combination of an achiral silicon-based Lewis acid and chiral Lewis base, such as iodotrimethylsilane (TMSI) and cinchonine, generated a highly enantioselective catalyst system under solvent-free conditions which gave aromatic beta-amino ketones with up to >99% ee. Mechanistic studies demonstrate the enhanced asymmetric induction may be due to the combined and competitive activation of a carbonyl moiety of chalcone with cinchonine and the silicon-based Lewis acid in the aza-Michael reaction.

  DOI：

  10.1021/ol202803b

文献信息

• Salicylato Titanocene Complexes as Cooperative Organometallic Lewis Acid and Brønsted Acid Catalysts for Three-Component Mannich Reactions
  作者：Ya Wu、Chun Chen、Gai Jia、Xuyang Zhu、Huaming Sun、Guofang Zhang、Weiqiang Zhang、Ziwei Gao

  DOI：10.1002/chem.201402438

  日期：2014.7.7

  A binary acid system has been developed that features an air‐stable organometallic precursor, titanocene dichloride, and simple organic cooperative Brønsted acids, which allowed for mild and highly efficient Mannich reactions of both aryl and alkyl ketones with excellent yields and satisfactory diastereoselectivity. Mechanistic studies, including 1H NMR titration, X‐ray structure analyses as well as

  已经开发了一种二元酸体系，其特征是具有空气稳定性的有机金属前体，二茂钛二氯化物和简单的有机协作布朗斯台德酸，可实现芳基和烷基酮的温和高效的曼尼希反应，并具有优异的收率和令人满意的非对映选择性。机理研究，包括1 H NMR滴定，X射线结构分析以及催化活性物质的分离，阐明了这种新的二元酸体系的巨大协同作用。
• Hf(OTf)4 as a Highly Potent Catalyst for the Synthesis of Mannich Bases under Solvent-Free Conditions
  作者：Shuai-Bo Han、Jing-Ying Wei、Xiao-Chong Peng、Rong Liu、Shan-Shan Gong、Qi Sun

  DOI：10.3390/molecules25020388

  日期：——

  Hf(OTf)4 was identified as a highly potent catalyst (0.1–0.5 mol%) for three-component Mannich reaction under solvent-free conditions. Hf(OTf)4-catalyzed Mannich reaction exhibited excellent regioselectivity and diastereoselectivity when alkyl ketones were employed as substrates. 1H NMR tracing of the H/D exchange reaction of ketones in MeOH-d4 indicated that Hf(OTf)4 could significantly promote the

  Hf(OTf)4 被确定为在无溶剂条件下进行三组分曼尼希反应的高效催化剂（0.1-0.5 mol%）。当使用烷基酮作为底物时，Hf(OTf)4 催化的曼尼希反应表现出优异的区域选择性和非对映选择性。酮在 MeOH-d4 中的 H/D 交换反应的 1H NMR 示踪表明 Hf(OTf)4 可以显着促进酮-烯醇互变异构化，从而有助于加快反应速率。
• Solvent strategy for unleashing the Lewis acidity of titanocene dichloride for rapid Mannich reactions
  作者：Ya Wu、Xiu Wang、Yanlong Luo、Jing Wang、Yajun Jian、Huaming Sun、Guofang Zhang、Weiqiang Zhang、Ziwei Gao

  DOI：10.1039/c5ra27094d

  日期：——

  The remarkable activation effect of alcohol solvent on kinetically inert titanocene dichloride was found to promote rapid three-component Mannich reactions. NMR and ESI-MS analyses as well as a control experiment of catalytic active species elucidated that the coordination of MeOH to the titanocene moiety unleashed the Lewis acid [Cp2Ti(OMe)2] and Brønsted acid HCl, which led to the enhanced catalytic

  发现醇溶剂对动力学惰性二茂钛二氯化物的显着活化作用促进了快速的三组分曼尼希反应。NMR和ESI-MS分析以及催化活性物种的对照实验表明，MeOH与二茂钛部分的配位释放出路易斯酸[Cp 2 Ti（OMe）2 ]和布朗斯台德HCl，从而增强了催化作用Cp 2 TiCl 2的活性。
• Cooperative Catalysis of <i>p</i>-Aminophenol and Titanocene Dichloride in Direct Mannich Reactions with Acetone
  作者：Xuyang Zhu、Chun Chen、Binxun Yu、Guofang Zhang、Weiqiang Zhang、Ziwei Gao

  DOI：10.1246/cl.140705

  日期：2014.12.5

  A new binary acid system featuring an air stable organometallic precursor, titanocene dichloride and a simple Brønsted acid–base compound, was developed. The new catalyst system allowed for mild and highly efficient direct three-component Mannich reactions of both aryl ketones and alkyl ketones, in particular, acetone and its derivatives with excellent yields. Mechanistic study elucidated the dramatic synergistic effect of the new binary acid system.

  开发了一种新型的二元酸体系，包含一种空气稳定的有机金属前驱体——二氯化钛烯，以及一种简单的布朗斯特酸碱化合物。该新催化剂体系使得芳香酮和烷基酮，特别是丙酮及其衍生物的直接三组分曼尼赫反应能够在温和的条件下高效进行，得到了优异的产率。机制研究阐明了这种新二元酸体系的显著协同效应。
• Titanocene dichloride and poly(o-aminophenol) as a new heterogeneous cooperative catalysis system for three-component Mannich reaction
  作者：Xuyang Zhu、Chun Chen、Binxun Yu、Ya Wu、Guofang Zhang、Weiqiang Zhang、Ziwei Gao

  DOI：10.1039/c5cy00793c

  日期：——

  A heterogeneous binary acid system featuring an organometallic precusor, titanocene dichloride, and poly(o-aminophenol) as a cooperative Brønsted acid supporter was developed.

  开发了一种含有有机金属前体、二氯化二茂钛和聚（o-氨基苯酚）作为协同Brønsted酸支持剂的异质二元酸体系。