N-[1-(2-furyl)-3-butenyl]phenylamine | 144661-27-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[1-(2-furyl)-3-butenyl]phenylamine
• 英文别名: N-phenyl-α-prop-2-enylfuran-2-methanamine；N-(1-(furan-2-yl)but-3-enyl)benzenamine；N-(1-(furan-2-yl)but-3-en-1-yl)aniline；4-(2-furan)-4-(phenyl)aminobut-1-ene；4-N-phenylamino-4-(2-furyl)butene-1；N-(1-(2-furyl)but-3-enyl)aniline；N-[1-(2-Furyl)-3-butenyl]aniline；N-[1-(furan-2-yl)but-3-enyl]aniline
• CAS: 144661-27-8
• 化学式: C₁₄H₁₅NO
• mdl: MFCD01126424
• 分子量: 213.279
• InChiKey: NHTXMDMUIXFGIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[1-(2-furyl)-3-butenyl]phenylamine 在 磷酸 作用下， 以 苯 为溶剂， 反应 25.0h， 生成 1-allyl-3-oxo-2-phenyl-2,3-dihydro-1H-isoindole-4-carboxylic acid
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1016047809349
• 作为产物：
  描述：

  烯丙基三甲氧基硅烷 、 N-糠基苯胺 在 silver trifluoromethanesulfonate 、 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三氟甲磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 15.33h， 以49%的产率得到N-[1-(2-furyl)-3-butenyl]phenylamine
  参考文献：
  名称：

  A silver triflate-catalyzed cascade of in situ-oxidation and allylation of arylbenzylamines

  摘要：

  A silver-triflate catalyzed cascade of in situ-oxidation and allylation of arylbenzylamines is reported. The 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate is employed as a mild oxidant which is compatible with both catalyst and ligand. Racemic BINAP is also utilized to assist with the catalyst in regulating the yields of products. Various homoallylic amines are obtained in 39-99% yields. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.06.076

文献信息

• Allylation of Aldehydes and Imines:  Promoted by Reuseable Polymer-Supported Sulfonamide of <i>N</i>-Glycine
  作者：Gui-long Li、Gang Zhao

  DOI：10.1021/ol0528235

  日期：2006.2.1

  [reaction: see text] A allylation of aldehydes and imines (generated in situ from aldehydes and amines) with allyltributyltin promoted by recoverable and reusable the polymer-supported sulfonamide of N-glycine has been developed. Good to high yields were obtained in various cases. Most of the SnBu(3) residue can be recovered as Bu(3)SnCl. Highly stereoselective synthesis of N-Boc-(2S,3S)-3-hydroxy-2-phenylpiperidine

  [反应：见正文]已开发了醛和亚胺（由醛和胺就地生成）与烯丙基三丁基锡的烯丙基化反应，该方法通过可回收和可重复使用的N-甘氨酸聚合物负载的磺酰胺促进。在各种情况下都获得了良好到高产。大多数的SnBu（3）残留物可以作为Bu（3）SnCl回收。N-Boc-（2S，3S）-3-羟基-2-苯基哌啶7的高度立体选择性合成是通过使用P4a介导的Boc-1-苯基甘氨酸的烯丙基化作为关键步骤实现的。
• Synthetic and Mechanistic Studies of Indium-Mediated Allylation of Imines in Ionic Liquids
  作者：Man Chun Law、Tin Wai Cheung、Kwok-Yin Wong、Tak Hang Chan

  DOI：10.1021/jo062198x

  日期：2007.2.1

  Aldimines derived from aryl and non-enolizable aliphatic aldehydes were allylated with allyl bromide mediated by indium powder in [bpy][BF4] (bpy = N-butylpyridine) to give good yields of the corresponding homoallylic amines. Selective formation of monoallylated amines can be achieved by varying the amount of bromide ion additive in the form of [bpy][Br]. The transient organoindium intermediates, allylindium(I)

  在[bpy] [BF 4 ]（bpy = N-丁基吡啶）中，将铟粉介导的烯丙基溴与烯丙基溴烯丙基化衍生自芳基和不可烯化的脂肪族醛的醛亚胺，以得到相应的均烯丙基胺良好的收率。可以通过改变[bpy] [Br]形式的溴离子添加剂的数量来实现单烯丙基化胺的选择性形成。通过NMR光谱研究了反应中形成的瞬态有机铟中间体，烯丙基（I）和烯丙基（III）二溴化物。
• Synthesis of polystyrene-bound perfluoroalkyl sulfonic acids and the application of their ytterbium salts in multicomponent reactions (MCRs)
  作者：Yueyan Yin、Gang Zhao、Gui-Long Li

  DOI：10.1016/j.tet.2005.08.118

  日期：2005.12

  New polystyrene-bound perfluoroalkyl sulfonic acids and their ytterbium salts have been prepared. Multicomponent reactions (MCRs) for the efficient synthesis of homoallylic amines or amides catalyzed by the polystyrene-bound perfluoroalkyl sulfonic ytterbium salts are reported.

  已经制备了新的聚苯乙烯结合的全氟烷基磺酸及其and盐。据报道，通过聚苯乙烯键合的全氟烷基磺酸盐催化的多组分反应（MCRs）可有效合成均烯丙基胺或酰胺。
• Montmorillonite Clay-Catalyzed Three-Component Coupling Reactions: A Facile Synthesis of Homoallylic Amines
  作者：J. S. Yadav、B. V. S. Reddy、A. Krishnam Raju、D. Gnaneshwar

  DOI：10.1002/1615-4169(200210)344:9<938::aid-adsc938>3.0.co;2-z

  日期：2002.10

  Homoallylic amines are synthesized by the three-component coupling reaction of aldehydes, amines and allyltributylstannane using a heterogeneous solid acid catalyst, montmorillonite KSF, under mild reaction conditions to afford the corresponding homoallylic amines in excellent yields.

  在温和的反应条件下，使用多相固体酸催化剂蒙脱土KSF，通过醛，胺和烯丙基三丁基锡烷的三组分偶联反应，可以合成均烯丙基胺，从而以优异的收率得到相应的均烯丙基胺。
• Aldehydes vs Aldimines. Unprecedented Aldimine-Selective Nucleophilic Additions in the Coexistence of Aldehydes Using a Lanthanide Salt as a Lewis Acid Catalyst
  作者：Shū Kobayashi、Satoshi Nagayama

  DOI：10.1021/ja971153y

  日期：1997.10.1

  It is well-recognized that aldimines are less reactive than aldehydes toward nucleophilic additions. In this paper, an unprecedented change in the reactivity is described: preferential reactions of aldimines over aldehydes in nucleophilic additions using a lanthanide salt as a Lewis acid catalyst. In the presence of a catalytic amount of ytterbium triflate (Yb(OTf)3), only aldimines reacted with silyl

  众所周知，醛亚胺对亲核加成的反应性低于醛。在本文中，描述了一种前所未有的反应性变化：在亲核加成中使用镧系元素盐作为路易斯酸催化剂，醛亚胺​​优先于醛反应。在催化量的三氟甲磺酸镱 (Yb(OTf)3) 存在下，只有醛亚胺与甲硅烷基烯醇醚、烯酮甲硅烷基缩醛、烯丙基三丁基锡烷或氰基三甲基硅烷反应，以高产率提供相应的加合物，即使在醛共存的情况下也是如此。13C NMR 分析表明选择性形成醛亚胺-Yb(OTf)3 复合物而不是醛-Yb(OTf)3 复合物。虽然这份报告证明了路易斯酸在有机合成中的有效利用，