2-[1-(4-methoxyphenyl)-1-(N-phenylamino)methyl]cyclohexanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[1-(4-methoxyphenyl)-1-(N-phenylamino)methyl]cyclohexanone
• 英文别名: 2-[(4-methoxyphenyl)(anilino)methyl]cyclohexanone；2-((4-methoxyphenyl)(phenylamino)methyl)cyclohexan-1-one；(2-(4-methoxy-phenyl)-phenylamino-methyl)-cyclohexanone；[1'-(N-phenylamino)-1'-(4-methoxyphenyl)]methylcyclohexanone；2-[Anilino-(4-methoxyphenyl)methyl]cyclohexan-1-one；2-[anilino-(4-methoxyphenyl)methyl]cyclohexan-1-one
• 化学式: C₂₀H₂₃NO₂
• 分子量: 309.408
• InChiKey: NLFGPJHFJHGZRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[1-(4-methoxyphenyl)-1-(N-phenylamino)methyl]cyclohexanone 、 2-(三甲基硅)苯基三氟甲烷磺酸盐 在 potassium fluoride 、 18-冠醚-6 、 盐酸 作用下， 以 乙腈 、 水 为溶剂， 反应 1.0h， 以45%的产率得到6-(4-methoxyphenyl)-5-phenyl-5,6,7,8,9,10-hexahydrophenanthridine
  参考文献：
  名称：

  通过苯炔的串联反应合成六氢菲啶

  摘要：

  已经描述了碳环β-氨基酮与苯炔之间的串联插入-环化反应，以中等至高收率生产六氢菲啶。

  DOI：

  10.1016/j.tet.2020.131372
• 作为产物：
  描述：

  2-(4-methoxybenzylidene)cyclohexanone 、 苯胺 反应 1.0h， 生成 2-[1-(4-methoxyphenyl)-1-(N-phenylamino)methyl]cyclohexanone
  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

• Three Component Mannich Reaction and 1,5-Benzodiazepine Synthesis Catalyzed by a Tetranitrile-Silver Complex
  作者：Gopalakrishnapanicker Krishnan、Radhakrishnan Sreerekha、Krishnapillai Sreekumar

  DOI：10.2174/157017809787003188

  日期：2009.1.1

  This manuscript describes the first example of silver ion complex of a dendritic tetranitrile ligand catalyzed one-pot three component Mannich reaction and 1,5-benzodiazepine synthesis. The catalyst can be separated from the products by a change in the solvent. The catalyst is reusable.

  本文稿描述了首例树枝状四氰基配体银离子复合物催化的一锅三组分Mannich反应及1,5-苯并二氮卓合成。通过改变溶剂，催化剂可从产物中分离。该催化剂可重复使用。
• Designing a novel tetradentate polyoxometalate eco-catalyst for the synthesis of β-aminocyclohexanone derivatives in water
  作者：Roya Mozafari、Fariba Heidarizadeh、Maedeh Azaroon

  DOI：10.1039/c8ra08259f

  日期：——

  designable cations and anions. Anions have two types of acids, acidic protons, and metals with Lewis acidity. In order to test the efficient catalytic behavior of the tetradentate catalyst, a controlled reaction was performed using benzaldehyde, aniline and cyclohexanone. Imine from the condensation of benzaldehyde and aniline was observed in the absence of ionic catalyst instead of desired products. Thus

  使用季戊四醇四甲基咪唑鎓磷钨酸盐 (C(MIM-PTA) 4 ) 作为新的四齿酸性催化剂，已经完成了一系列已知的 β-氨基环己酮的合成。由季戊四醇四溴化物与甲基咪唑缩合而成。然后，用Br -取代大体积阴离子H 2 PW 12 O 40 1-在结构中。这种四齿催化剂提供可设计的阳离子和阴离子。阴离子有两种类型的酸，酸性质子和具有路易斯酸性的金属。为了测试四齿催化剂的有效催化行为，使用苯甲醛、苯胺和环己酮进行受控反应。在不存在离子催化剂而不是所需产物的情况下观察到来自苯甲醛和苯胺缩合的亚胺。因此，由于不存在中间体的分离和立体专一性，该反应由于时间、能量和节省原材料的考虑将是有吸引力的。该催化剂显示出高催化活性，使得经过四次循环后，得到高收率和高纯度的产物。该反应在室温下进行。虽然高温可以提高反应速率，但它有助于醛和胺的副反应和氧化。催化剂通过元素分析、FT-IR光谱、1 H NMR、 13 C
• Direct Asymmetric Mannich Reaction Catalyzed by a d-Glucosamine-Derived Organocatalyst
  作者：Rama Peddinti、Arun Sharma

  DOI：10.1055/s-0036-1591740

  日期：2018.3

  Sugar-based primary amines have been employed as organocatalysts for the direct asymmetric Mannich reaction. By catalyst-screening experiments, we observed that catalysts bearing a hydroxy function at C-3 actively participated in the reaction, possibly through hydrogen bonding with the imine generated in situ, to provide β-amino carbonyl compounds with better diastereoselectivity and enantioselectivity

  糖基伯胺已被用作直接不对称曼尼希反应的有机催化剂。通过催化剂筛选实验，我们观察到在 C-3 处带有羟基官能团的催化剂积极参与反应，可能是通过与原位生成的亚胺形成氢键，从而提供具有更好非对映选择性和对映选择性的 β-氨基羰基化合物。获得的所有产品都处于良好至极好的对映体过量。
• Brønsted acid-surfactant-combined catalyst for the Mannich reaction in water
  作者：Tao Chang、Leqin He、Li Bian、Haiyan Han、Mingxia Yuan、Xiaorui Gao

  DOI：10.1039/c3ra44726j

  日期：——

  A series of Brønsted acid-surfactant-combined catalysts (BASCs) functionalised with different acids have been synthesized and applied to catalyze the three-component Mannich reaction with aldehyde, acetone and amine at 25 °C in water. The effects of cation tail length and ions of the ionic liquid and the recyclability of the catalysts and BASC acidity (H0) were investigated. The results demonstrated that the 3-(N,N-dimethyloctylammonium) propanesulfonic acid toluene sulfate ([DOPA][Tos]) provide the best catalytic activity because of the formation of emulsions during the reaction. The catalytic procedure was simple and the catalyst could be recycled 9 times by simple separating processes without noticeably decreasing the catalytic activity.

  研究人员合成了一系列用不同酸进行官能化的布氏酸-表面活性剂复合催化剂（BASCs），并将其用于催化醛、丙酮和胺在 25 °C 水中的三组分曼尼希反应。研究了离子液体的阳离子尾长和离子的影响以及催化剂的可回收性和 BASC 酸度 (H0)。结果表明，3-（N,N-二甲基辛基铵）丙磺酸甲苯硫酸盐（[DOPA][Tos]）的催化活性最好，因为在反应过程中会形成乳状液。催化过程简单，催化剂可通过简单的分离过程循环使用 9 次，而催化活性不会明显降低。
• An environmentally friendly, photocontrollable and highly recyclable catalyst for use in a one-pot three-component Mannich reaction
  作者：Qian Tang、Hong-jiang Quan、Song Liu、Lan-tao Liu、Cheuk-fai Chow、Cheng-bin Gong

  DOI：10.1016/j.molcata.2016.05.006

  日期：2016.9

  H was investigated towards the one-pot three-component Mannich-type reaction of benzaldehyde, aniline and cyclohexanone in water at room temperature, and gave excellent yields. Interestingly, the catalytic activity could be regulated by photoirradiation. Furthermore, upon completion of the reaction, the product could be readily separated by extraction, and the water phase reused in the next run. Lastly

  摘要 通过将4-[4-(6-膦酸-己氧基)苯基偶氮基]苯磺酸固定在膦酸锆上，合成了一种环境友好、光控、高度可回收的催化剂(ZrOPPAZOSO 3 H)。该催化剂通过傅里叶变换红外、扫描电子显微镜、X射线粉末衍射、氮吸附-解吸和紫外-可见分析进行了表征。研究了ZrOPPAZOSO 3 H在室温下对水中苯甲醛、苯胺和环己酮的一锅三组分曼尼希型反应的催化活性，并获得了优异的收率。有趣的是，催化活性可以通过光辐照来调节。此外，反应完成后，产物可以很容易地通过萃取分离，水相在下一次运行中重新使用。最后，