N-(phenyl)-α-(3-phenyl-2-propenyl)benzemethanamine

• 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: N-(phenyl)-α-(3-phenyl-2-propenyl)benzemethanamine
• 英文别名: N-(1,4-diphenylbut-3-enyl)benzeneamide；(E)-N-(1,4-diphenylbut-3-enyl)aniline；N-((E)-1,4-diphenylbut-3-enyl)benzenamine；N-[(E)-1,4-diphenylbut-3-enyl]aniline
• 化学式: C₂₂H₂₁N
• 分子量: 299.415
• InChiKey: KWHXMPPZWPYSSI-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  烯丙苯 、 N-苄叉苯胺 在 sodium hexamethyldisilazane 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以96%的产率得到N-(phenyl)-α-(3-phenyl-2-propenyl)benzemethanamine
  参考文献：
  名称：

  由酰胺钠引发的烯烃的形式烯丙基 C(sp3)-H 键活化

  摘要：

  氨基钠的催化用途已被用于在温和条件下烯烃的正式烯丙基 C(sp3)-H 键活化。随后与亚胺的 CC 键形成以高产率进行，具有完全的区域选择性和优异的几何选择性。不含过渡金属的催化剂可耐受芳香族氰基、氯和溴官能团。带有 C=C 双键和不同杂芳族单元的复合胺已在一个步骤中制备。钠相对于其他 s-、p-、d- 和 f-嵌段金属以及无金属系统的关键重要性已被揭示。此外，通过 NMR 和 HRMS 分析检测到两种具有催化活性的钠基中间体。

  DOI：

  10.1021/jacs.7b01542

文献信息

• Facile synthesis of homoallylamines via α-regioselectivity in ultrasonic mediation and γ-adduct syn-stereoselective allylation with AlCl3-catalysis
  作者：Chuo-Yu Lee、Ya-Chuan Yen、Adam Shih-Yuan Lee

  DOI：10.1016/j.tetlet.2024.155134

  日期：2024.7

  The allylation reaction of aldimines with allyl metal reagents is an important synthetic method for the preparation of homoallylamines. Therefore, we wish to report a highly regioselective and stereoselective allylation reaction under sonochemical Barbier-type reaction conditions. The high yields of regioselective α-adducts were achieved by reacting cinnamyl bromide, zinc, 1,2-dibromoethane, and aldimine

  醛亚胺与烯丙基金属试剂的烯丙基化反应是制备高烯丙胺的重要合成方法。因此，我们希望报道在声化学Barbier型反应条件下的高度区域选择性和立体选择性烯丙基化反应。通过使肉桂基溴、锌、1,2-二溴乙烷和醛亚胺在 THF 中在声化学 Barbier 型条件下反应，获得了高产率的区域选择性 α-加合物。在路易斯酸促进的巴比耶型反应条件下也实现了高度区域选择性和立体选择性烯丙基化反应。
• Allylic-Type Diindium Reagents. Reactivity toward Electrophiles and Cascade Coupling Reactions with Imines
  作者：Tsunehisa Hirashita、Yousuke Hayashi、Kazuma Mitsui、Shuki Araki

  DOI：10.1021/jo026609v

  日期：2003.2.1

  The allylic-type diindium reagents A and B were prepared from 3-bromo-1-iodopropene (1a) and 4-bromo-2-iodobut-2-ene (1b), respectively, and their reactions with electrophiles were investigated. The diindium reagents A and B were initially reacted with imines and the resulting vinylindium compounds were then treated with organic halides in the presence of Pd(PPh3)(4) to give linear N-aryl and N-tosyl homoallylic amines. Diindium A is stable in a small amount of water in solvent, whereas B is easily protonated to give a crotylindium reagent. The reaction of B with benzaldehyde gives mainly the 1,3- and 1,5-diols via a spontaneous coupling with two molecules of the aldehyde, in contrast to A, which reacts with one molecule of carbonyl compounds to give the vinylindium compounds.
• Allylation of Imines with Allyltrimethylsilane and Experimental Evidences for a Fluoride-Triggered Autocatalysis Mechanism of the Sakurai−Hosomi Reaction
  作者：De-Kun Wang、Yong-Gui Zhou、Yong Tang、Xue-Long Hou、Li-Xin Dai

  DOI：10.1021/jo980767y

  日期：1999.6.1

  This article reports the reaction of allyltrimethylsilane 1 with aldimines 2 in the presence of tetra-n-butylammonium fluoride to give the corresponding homoallylamines 3 in moderate to excellent yields. The allylation mechanism of imines as well as that of aldehydes can be reasonably interpreted by a fluoride-triggered autocatalytic procedure.