3-(4-chlorophenyl)-1-phenyl-3-(phenylamino)propan-1-one | 119948-33-3

• 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-(4-chlorophenyl)-1-phenyl-3-(phenylamino)propan-1-one
• 英文别名: 1-phenyl-3-(p-chlorophenyl)-3-phenylamino-1-propanone；3-(4-chlorophenyl)-1-phenyl-3-(N-phenylamino)propan-1-one；3-anilino-3-(4-chlorophenyl)-1-phenylpropan-1-one
• CAS: 119948-33-3
• 化学式: C₂₁H₁₈ClNO
• 分子量: 335.833
• InChiKey: FFCGWRGWOZNCQH-UHFFFAOYSA-N

物化性质

• 熔点：
  114-115 °C
• 沸点：
  522.4±45.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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-(4-chlorophenyl)-1-phenyl-3-(phenylamino)propan-1-one 在 1-propylsulfonate-3-methylimidazolium trifluoromethanesulfonate 、 1-butyl-3-ethylimidazolium hexafluorophosphate 、 Selectfluor 作用下， 反应 3.0h， 以72%的产率得到4-氯查耳酮
  参考文献：
  名称：

  Mild and selective α-fluorination of carbonyl compounds (ketones, 1,3-diketones, β-ketoesters, α-nitroketones, and β-ketonitriles) with Selectfluor (F-TEDA-BF4) in imidazolium ILs [BMIM/PF6 or BMIM/NTf2] with Brønsted-acidic IL [PMIM(SO3H)/OTf] as promoter

  摘要：

  Structurally diverse ketones, 1,3-diketones, and beta-ketoesters, were selectively monofluorinated with Selectfluor (F-TEDA-BF4) (1 equiv) in [BMIM][PF6] as solvent and [PMIM(SO3H)][OTf] as promoter under mild conditions. In selected cases, the monofluorinated products were transformed to the gem-difluoro derivatives by employing an additional equivalent of Selectfluor, and gem-difluoro-derivatives were synthesized directly from the substrates by employing 2 equiv of Selectfluor. The method was extended to monofluorination of representative alpha-nitroketones and beta-ketonitriles using [BMIM][NTf2] without the need for promoters. The described method offers the added advantage of recycling and reuse of the IL solvent.

  DOI：

  10.1016/j.tetlet.2015.07.084
• 作为产物：
  描述：

  4-氯苯甲醛 在 alkylphenylsulfonic acid functionalized silica coated magnetic Fe₃O₄ nanoparticle 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 3-(4-chlorophenyl)-1-phenyl-3-(phenylamino)propan-1-one
  参考文献：
  名称：

  A magnetic solid sulfonic acid modified with hydrophobic regulators: an efficient recyclable heterogeneous catalyst for one-pot aza-Michael-type and Mannich-type reactions of aldehydes, ketones, and amines

  摘要：

  Two convenient green protocols for the synthesis of 3-amino ketones have been developed which involve one-pot aza-Michael-type and Mannich-type reactions of a series of aldehydes, ketones, and amines in the presence of a catalytic amount of the magnetic solid sulfonic acid catalyst, Fe3O4@SiO2@Me&Et-PhSO3H, at room temperature. The catalyst can be reused four times without loss of activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.02.088

文献信息

• Strong Lewis Acids of Air-Stable Metallocene Bis(perfluorooctanesulfonate)s as High-Efficiency Catalysts for Carbonyl-Group Transformation Reactions
  作者：Renhua Qiu、Xinhua Xu、Lifeng Peng、Yalei Zhao、Ningbo Li、Shuangfeng Yin

  DOI：10.1002/chem.201103874

  日期：2012.5.14

  that 2 a and 2 b were thermally stable at 300 and 180 °C, respectively. These complexes exhibited unusually high solubility in polar organic solvents. Conductivity measurement showed that the complexes (2 a and 2 b) were ionic dissociation in CH3CN solution. X‐ray analysis result confirmed 2 a⋅3 H2O⋅THF was a cationic organometallic Lewis acid. UV/Vis spectra showed a significant red shift due to the

  强路易斯酸空气中稳定的金属茂双（全氟辛烷磺酸盐）S [M（CP）2 ] [OSO 2 C ^ 8 ˚F 17 ] 2 ⋅ Ñ ħ 2 O⋅THF（M = Zr的（2 ⋅3ħ 2 O⋅THF ），M =的Ti（图2b ⋅2ħ 2 O⋅THF））由[M（CP）的反应合成2 ]氯2（M = Zr的（1），M =的Ti（图1b）），与n BuLi和C 8 F 17 SO 3 H（2当量）或与C 8 F 17 SO 3Ag（2当量）。这些配合物的水合物数（n）是可变的，取决于条件从0变为4。与众所周知的茂金属三氟甲磺酸盐相反，这些络合物在露天环境中一年没有变化。热重-差示扫描量热（TG-DSC）分析表明，2和图2b分别为300和180℃，是热稳定的。这些配合物在极性有机溶剂中显示出异常高的溶解度。电导率测量表明，络合物（2a和2b）在CH 3 CN溶液中呈离子离解。X射线分析结果确认为2 a⋅3H
• 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。
• Strong Lewis acid air-stable cationic titanocene perfluoroalkyl(aryl)sulfonate complexes as highly efficient and recyclable catalysts for C–C bond forming reactions
  作者：Ningbo Li、Jinying Wang、Xiaohong Zhang、Renhua Qiu、Xie Wang、Jinyang Chen、Shuang-Feng Yin、Xinhua Xu

  DOI：10.1039/c4dt00549j

  日期：——

  A series of titanocene perfluoroalkyl(aryl)sulfonate complexes were synthesized, characterized, and applied in various C–C bond forming reactions.

  一系列的钛ocene基过氟烷基（芳基）磺酸盐配合物被合成、表征，并应用于各种C-C键形成反应。
• Brønsted Acid-Catalyzed Mannich-Type Reactions in Aqueous Media
  作者：Takahiko Akiyama、Jun Takaya、Hirotaka Kagoshima

  DOI：10.1002/1615-4169(200206)344:3/4<338::aid-adsc338>3.0.co;2-o

  日期：2002.6

  aldimines took place smoothly in aqueous organic solvent to afford β-aminocarbonyl compounds in high yields. The HBF4-catalyzed Mannich-type reaction also proceeded smoothly in water without organic solvent in the presence of a surfactant. A three-component synthesis starting from aldehyde, amine, and silyl enolate was successfully realized by means of a Bronsted acid in aqueous media.

  HBF4催化的甲硅烷基烯醇化物与醛亚胺的曼尼希型反应在水性有机溶剂中顺利进行，以高产率得到β-氨基羰基化合物。在表面活性剂存在下，HBF4催化的曼尼希型反应在没有有机溶剂的水中也能顺利进行。借助布朗斯台德酸在水性介质中成功实现了从醛、胺和烯醇甲硅烷基开始的三组分合成。
• 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。