2-[1'-(2-furyl)-1'-N-phenylamino]methylcyclohexanone

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-[1'-(2-furyl)-1'-N-phenylamino]methylcyclohexanone
• 英文别名: 2-[Anilino(furan-2-yl)methyl]cyclohexan-1-one
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: PSSHYCSUOGAMHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  糠醛 、 1-环己烯氧基三甲基硅烷 、 苯胺 在 bismuth triflate tetrahydrate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以78%的产率得到2-[1'-(2-furyl)-1'-N-phenylamino]methylcyclohexanone
  参考文献：
  名称：

  一种高效，温和的三氟甲磺酸铋催化的三组分曼尼希型反应。

  摘要：

  在催化量的Bi（OTf）（3）.4H（2）O的存在下，醛与胺一起与甲硅烷基烯醇酸酯反应，可平稳地提供相应的曼尼希型加合物。多种衍生自酮以及酯和硫代酯的甲硅烷基烯醇化物迅速反应，以高收率（高达94％）提供β-氨基酮或β-氨基酯。

  DOI：

  10.1039/b710794c

文献信息

• 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。
• Carbohydrate-Based Tolylsulfonyl Hydrazines: Effective Catalysts for the Mannich Reaction and the Syntheses of Bisindolylalkanes in Water
  作者：Peng Wu、Yiqian Wan、Jiwen Cai

  DOI：10.1071/ch08004

  日期：——

  Three carbohydrate-based tolylsulfonyl hydrazines were used to catalyze the three-component Mannich reaction, as well as the adduct reaction of aldehyde and indole to prepare bisindolylalkanes in water. Moderate to good yields were achieved. The results demonstrate that carbohydrate derivatives can be employed as effective catalysts in water, and an environmentally benign methodology was developed to synthesize bioactive bisindolylalkanes and the β-amino carbonyl framework.

  我们使用了三种基于碳水化合物的甲苯磺酰肼来催化三组分曼尼希反应以及醛和吲哚的加成反应，从而在水中制备出双吲哚烷烃。获得了中等到良好的产率。研究结果表明，碳水化合物衍生物可用作水中的有效催化剂，并开发出一种无害环境的方法来合成具有生物活性的双吲哚烷烃和β-氨基羰基框架。
• Polyelectrolyte Brønsted acid catalyzed three-component Mannich reactions accelerated by emulsion
  作者：Xi Chen、Huaming Sun、Yanlong Luo、Yajun Jian、Ya Wu、Weiqiang Zhang、Ziwei Gao

  DOI：10.1039/c6ra04180a

  日期：——

  An effective polyelectrolyte Bronsted acid (polyacrylic acid) catalyzed three-component Mannich reactions accelerated by emulsion has been developed. The results demonstrated that the polyacrylic acid provided the best catalytic activity in...

  已开发出一种有效的聚电解质布朗斯台德酸（聚丙烯酸）催化由乳液加速的三组分曼尼希反应。结果表明，聚丙烯酸具有较好的催化活性。
• Mannich-type reactions of aromatic aldehydes, anilines, and methyl ketones in fluorous biphase systems created by rare earth (III) perfluorooctane sulfonates catalysts in fluorous media
  作者：Wen-Bin Yi、Chun Cai

  DOI：10.1016/j.jfluchem.2006.07.009

  日期：2006.11

  Rare earth (III) perfluorooctane sulfonates (RE(OPf)3) catalyze the three-component Mannich-type reactions of different ketones with various aromatic aldehydes and aromatic amines in fluorous media to give various β-arylamino ketones in good yields. By simple separation of the fluorous phase containing only catalyst, reaction can be repeated several times.

  稀土（III）全氟辛烷磺酸盐（RE（OPf）3）在氟介质中催化不同酮与各种芳香醛和芳香胺的三组分曼尼希型反应，以高收率得到各种β-芳基氨基酮。通过仅含催化剂的氟相的简单分离，反应可重复数次。
• Nafion-H®: A recyclable and diastereoselective solid acid catalyst for three-component mannich reaction
  作者：Yang Suling、Li Gang、Long Yunling

  DOI：10.1134/s0023158412060079

  日期：2012.11

  One-pot, three-component Mannich reactions of ketones, aldehydes and amines are efficiently catalyzed by heterogeneous Nafion-H® ambient temperature to give the corresponding β-amino ketones compounds in good to excellent yields. The catalyst can be easily recovered and reused without any decrease of activity for at least four times. Diastereoselective products can be obtained in Mannich reaction of aliphatic

  异构的Nafion-H®环境温度可有效催化酮，醛和胺的一锅，三组分曼尼希反应，从而以良好或极好的收率得到相应的β-氨基酮化合物。催化剂可以容易地回收和再利用，而活性至少四次没有降低。非对映选择性产物可以在脂肪族酮的曼尼希反应中获得。