2-methyl-1-phenyl-1-[N-(4-methylphenyl)amino]pentan-3-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methyl-1-phenyl-1-[N-(4-methylphenyl)amino]pentan-3-one
• 英文别名: syn-2-methyl-1-phenyl-1-(p-tolylamino)pentan-3-one；(1R,2R)-2-methyl-1-(4-methylanilino)-1-phenylpentan-3-one
• 化学式: C₁₉H₂₃NO
• 分子量: 281.398
• InChiKey: LVMAOGAPIPECGY-HNAYVOBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯甲醛 、 乙烷,三氯氟- 、 3-戊酮 在 5-磺基水杨酸 作用下， 以 水 为溶剂， 反应 7.0h， 以83%的产率得到2-methyl-1-phenyl-1-[N-(4-methylphenyl)amino]pentan-3-one
  参考文献：
  名称：

  5-磺基水杨酸在纯水中催化曼尼希直接反应

  摘要：

  水溶性布朗斯台德酸5-磺基水杨酸可在纯水中有效催化环己酮和3-戊酮的直接三组分曼尼希反应。给出了21个Mannich反应的例子，该例子提供了相应的β-氨基酮，产率高达97％，非对映选择性也不错。酸催化剂可以水溶液形式循环至少六次，曼尼希产品的产率保持在90％以上。

  DOI：

  10.1016/j.molcata.2014.08.017

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。
• One-pot three-component Mannich-type reaction catalyzed by trifluoromethanesulfonic acid in water
  作者：Gang Li、Hankui Wu、Zhiyong Wang、Xianli Wang

  DOI：10.1134/s0023158411010113

  日期：2011.2

  One-pot three-component Mannich-type reaction of ketones, aldehydes and amines was efficiently catalyzed by liquid trifluoromethanesulfonic acid in water at ambient temperature. The high yield of corresponding β-amino ketones compounds were achieved. The proposed method is mild, green, simple and efficient.

  在环境温度下，液体三氟甲磺酸在水中能有效地催化酮，醛和胺的一锅三组分曼尼希型反应。实现了高产率的相应β-氨基酮化合物。该方法温和，绿色，简单，有效。
• Mannich Reaction of Imines and Silyl Enol Ethers Induced by Radical Cation Salts: Synthesis of β-Amino Ketones
  作者：Xiao-dong Jia、Xi-cun Wang、Wen-juan Wang、Cong-de Huo、Zheng-jun Quan、Yan Ren

  DOI：10.1055/s-0030-1259036

  日期：2010.12

  Mannich reaction of imines and sily enol ethers induced by radical cation salts was investigated and a series of β-amino ketones were synthesized. Reverse diastereoselectivity was obtained in the reactions of imines and silyl enol ethers of pentan-2-one and pentan-3-one, respectively, which was rationalized by quantum mechanical calculations. A single electron-transfer mechanism was proposed in which

  研究了自由基阳离子盐诱导亚胺与甲硅烷基烯醇醚的曼尼希反应，合成了一系列β-氨基酮。分别在pentan-2-one和pentan-3-one的亚胺和甲硅烷基烯醇醚的反应中获得了反向非对映选择性，这通过量子力学计算得到了合理化。提出了一种单一的电子转移机制，其中亚胺自由基阳离子在这种转变中充当亲电子物种。
• Aluminium dodecatungstophosphate (AlPW12O40)—An efficient catalyst for three-component Mannich reaction in water
  作者：Gang Li、Ruiling Long、Suling Yang、Liping Zhang

  DOI：10.1134/s0023158411040045

  日期：2011.7

  One-pot, three-component Mannich reactions of ketones, aldehydes and amines were efficiently catalyzed by AlPW12O40 in water at ambient temperature to give the corresponding beta-amino ketones in good to excellent yields. The method has the following merits: Firstly, Catalyst AlPW12O40 is non-corrosive and environmentally benign; Secondly, loading amount of catalyst is very low, less than 1 mol %; Thirdly, water as solvent is green and safe.
• 5-Sulfosalicylic acid catalyzed direct Mannich reaction in pure water
  作者：Chun Chen、Xuyang Zhu、Ya Wu、Huaming Sun、Guofang Zhang、Weiqiang Zhang、Ziwei Gao

  DOI：10.1016/j.molcata.2014.08.017

  日期：2014.12

  A water-soluble Brønsted acid, 5-sulfosalicylic acid, efficiently catalyzed the direct three-component Mannich reactions of cyclohexanone and 3-pentanone in pure water. 21 Examples of Mannich reactions were presented, which afforded the corresponding β-amino ketones with up to 97% yield and decent diastereoselectivities. The acid catalyst can be recycled as an aqueous solution for at least six times

  水溶性布朗斯台德酸5-磺基水杨酸可在纯水中有效催化环己酮和3-戊酮的直接三组分曼尼希反应。给出了21个Mannich反应的例子，该例子提供了相应的β-氨基酮，产率高达97％，非对映选择性也不错。酸催化剂可以水溶液形式循环至少六次，曼尼希产品的产率保持在90％以上。