2-[(3-nitrophenyl)(phenylamino)methyl]cyclohexanone

• 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-[(3-nitrophenyl)(phenylamino)methyl]cyclohexanone
• 英文别名: (2R)-2-[(S)-anilino-(3-nitrophenyl)methyl]cyclohexan-1-one
• 化学式: C₁₉H₂₀N₂O₃
• 分子量: 324.379
• InChiKey: PUEYZYDQLGNUHY-PKOBYXMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  环己酮 、 间硝基苯甲醛 、 苯胺 在 ethane-1,2-diaminium hydrogen sulfate 作用下， 以 乙醇 为溶剂， 反应 0.2h， 以87%的产率得到2-[(3-nitrophenyl)(phenylamino)methyl]cyclohexanone
  参考文献：
  名称：

  乙烷-1,2-硫酸氢二胺：通过三组分曼尼希反应一锅法合成β-氨基酮的可回收有机催化剂

  摘要：

  合成了 1,2-硫酸氢乙烷并通过 NMR 和元素分析技术对其进行了表征，发现对酮与芳香醛和芳香胺在乙醇中的一锅曼尼希型反应具有较高的催化效率。该方法具有条件温和、原料易得、与多种功能兼容、后处理程序简单等优点。该催化剂还显示出良好的可回收性和可重复使用性。

  DOI：

  10.3184/174751914x13939287092503

文献信息

• 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。
• Cs2.5H0.5PW12O40 catalyzed diastereoselective synthesis of β-amino ketones via three component Mannich-type reaction in water
  作者：Ezzat Rafiee、Sara Eavani、Fereshte Khajooei Nejad、Mohammad Joshaghani

  DOI：10.1016/j.tet.2010.06.052

  日期：2010.8

  compounds were prepared and used as catalysts for the Mannich-type reaction of benzaldehyde, aniline, and cyclohexanone in water. Among them, Cs2.5H0.5PW12O40 showed excellent catalytic activity. Effects of surfactant, catalyst loading and temperature were studied to introduce the best reaction condition. The optimized reaction conditions were extended to Mannich reaction of various aldehydes, ketones

  制备了一系列Keggin杂多化合物的不溶盐，并将其用作水中苯甲醛，苯胺和环己酮的曼尼希型反应的催化剂。其中，Cs 2.5 H 0.5 PW 12 O 40表现出优异的催化活性。研究了表面活性剂，催化剂负载量和温度的影响，以引入最佳反应条件。优化的反应条件扩展到各种醛，酮和胺在水中的曼尼希反应。这种快速的过程提供了具有主要抗非对映选择性的结构多样化的β-氨基酮。另外，据报道有四种新化合物。回收催化剂并将其再用于后续操作。
• Acid-ionic polymer as recyclable catalyst for one-pot three-component Mannich reaction
  作者：W. Senapak、R. Saeeng、U. Sirion

  DOI：10.1039/c7ra04834c

  日期：——

  A recyclable solid-catalyst, acid-ionic polymer bearing imidazolium trifluoromethanesulfonate, [PS-Im][OTf] was presented as an efficient catalyst in a one-pot, three-component Mannich reaction of aldehydes, amines and ketones. The protocol was conducted successfully under mild, convenient and metal-free conditions to afford the corresponding products in moderate to excellent yields. In addition, the

  提出了一种可循环使用的固体催化剂，带有三氟甲磺酸咪唑鎓盐[PS-Im] [OTf]的酸离子聚合物，它是醛，胺和酮的一锅，三组分曼尼希反应中的一种有效催化剂。该方案在温和，方便和无金属的条件下成功进行，以中等至极好的收率提供了相应的产品。另外，该催化剂被重复使用了四次而活性没有明显损失。
• Diastereoselective three-component Mannich reaction catalyzed by silica-supported ferric hydrogensulfate
  作者：Hossein Eshghi、Mohammad Rahimizadeh、Mohsen Hosseini、Aida Javadian-Saraf

  DOI：10.1007/s00706-012-0800-y

  日期：2013.2

  AbstractA highly anti-diastereoselective three-component Mannich reaction of aromatic amines and aromatic aldehydes with cyclohexanone in the presence of silica-supported ferric hydrogensulfate has been developed. The best selectivity was obtained where there were electron-donating groups on both aldehyde and amine. Selectivity decreases when electron-withdrawing groups are present on the aldehyde;

  摘要高度抗芳族胺，并用在二氧化硅负载的三价铁氢盐的存在下的环己酮的芳香醛的-diastereoselective三组分曼尼希反应已经研制成功。在醛和胺上均具有给电子基团的情况下，可获得最佳的选择性。当在醛上存在吸电子基团时，选择性降低。在这些情况下，如果胺上存在供电子基团，则选择性会提高。 图形概要
• Highly efficient one-pot three-component Mannich reaction catalyzed by ZnO-nanoparticles in water
  作者：David I. MaGee、Minoo Dabiri、Peyman Salehi、Laleh Torkian

  DOI：10.3998/ark.5550190.0012.b14

  日期：——

  ZnO-nanoparticles, as a recyclable heterogeneous catalyst, efficiently promoted the one-pot threecomponent Mannich reaction of ketones, aromatic aldehydes and amines in water to afford the corresponding β-amino carbonyl compounds in good to excellent yields and with moderate diastereoselectivity. The method offers a new modification of the Mannich reaction with a simple workup procedure.

  ZnO-纳米颗粒作为一种可回收的多相催化剂，有效地促进了酮、芳香醛和胺在水中的一锅三组分曼尼希反应，以良好的收率和中等的非对映选择性提供相应的β-氨基羰基化合物。该方法通过简单的后处理程序对曼尼希反应进行了新的改进。