3-(naphthalen-1-yl)-1-phenyl-3-phenylamino-propan-1-one | 502614-90-6

• 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-(naphthalen-1-yl)-1-phenyl-3-phenylamino-propan-1-one
• 英文别名: 3-(naphthalen-1-yl)-1-phenyl-3-phenylaminopropan-1-one；1-Propanone, 3-(1-naphthalenyl)-1-phenyl-3-(phenylamino)-；3-anilino-3-naphthalen-1-yl-1-phenylpropan-1-one
• CAS: 502614-90-6
• 化学式: C₂₅H₂₁NO
• 分子量: 351.448
• InChiKey: DNTLLVIVASFHDH-UHFFFAOYSA-N

物化性质

• 沸点：
  575.2±43.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 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-(naphthalen-1-yl)-1-phenyl-3-phenylamino-propan-1-one 在 indium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以83%的产率得到苯基[2-(1-萘基)乙烯基]甲酮
  参考文献：
  名称：

  铟（III）的三氟甲磺酸盐催化查尔酮的Aza-Michael加合物与芳香胺的反应：Retro-Michael加成与喹啉的形成

  摘要：

  研究了查尔酮的氮杂-迈克尔加合物与芳族胺的三氟甲磺酸铟（III）催化反应。衍生自取代苯胺和查耳酮的迈克尔加合物进行了逆迈克尔加成反应，得到了原始原料，而衍生自1-萘胺和查耳酮的迈克尔加合物得到了喹啉。有人提出了六元环过渡态来解释反迈克尔加成反应，而提出了一种Povarov机理来解释喹啉的形成。

  DOI：

  10.1021/acs.joc.7b03151
• 作为产物：
  描述：

  1-苯基-1-三甲基硅氧乙烯 、 (E)-N-(naphthalen-1-ylmethylene)aniline 在 ytterbium triflate on poly(4-vinylpyridine/styrene) resin 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.0h， 生成 3-(naphthalen-1-yl)-1-phenyl-3-phenylamino-propan-1-one
  参考文献：
  名称：

  Cross-linked poly(4-vinylpyridine/styrene) copolymers as a support for immobilization of ytterbium triflate

  摘要：

  Eight cross-linked poly(4-vinylpyridine/styrene) (P/S) resins (as beads) were prepared by radical suspension polymerization. Ytterbium triflate was immobilized in the range of 0.10-0.24 mmol/g by mixing with the P/S resins. The ytterbium triflate-immobilized P/S resins exhibited good activity in two Lewis acid-catalyzed reactions. Low pyridine containing resins were recycled with no loss of activity, while a slight loss of activity was observed with the higher pyridine containing resins. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.068

文献信息

• An efficient and mild bismuth triflate-catalysed three-component Mannich-type reaction
  作者：Thierry Ollevier、Etienne Nadeau

  DOI：10.1039/b710794c

  日期：——

  In the presence of a catalytic amount of Bi(OTf)(3).4H(2)O, aldehydes together with amines react with silyl enolates to afford the corresponding Mannich-type adducts smoothly. A wide variety of silyl enolates derived from ketones, as well as esters and thioesters, react rapidly to afford the beta-amino ketones or the beta-amino esters in high yields (up to 94%).

  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。
• Molecular Iodine-Catalyzed Imine Activation for Three-Component ­Nucleophilic Addition Reactions
  作者：Kim Janda、Byoung Lee、Suresh Mahajan

  DOI：10.1055/s-2005-868487

  日期：——

  β-Amino ketones and α-amino nitriles were synthesized from silyl enol ethers and trimethylsilyl cyanides, via a three-component nucleophilic addition reaction with aromatic aldehydes and amines; the reaction was found to be significantly accelerated by molecular iodine under neutral conditions.

  β-氨基酮和α-氨基腈由甲硅烷基烯醇醚和三甲基甲硅烷基氰化物通过与芳香醛和胺的三组分亲核加成反应合成；发现在中性条件下分子碘可显着加速反应。
• Novel method for catalyst immobilization using an ionic polymer: a case study using recyclable ytterbium triflate
  作者：Byoung Se Lee、Suresh Mahajan、Kim D. Janda

  DOI：10.1016/j.tetlet.2004.12.013

  日期：2005.1

  A series of ionic polymers prepared by quarternization of cross-linked poly(4-vinylpyridine/styrene) (P/S) resins with several alkylating agents, including short-length PEG mesylate were used as polymeric supports to immobilize Yb(OTf)(3). The efficacy of the polymer-bound catalyst was examined in a Mannich-type reaction. (C) 2004 Elsevier Ltd. All rights reserved.