naphthalene-1-yl(1-phenylbut-3-enyl)amine | 241819-54-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthalene-1-yl(1-phenylbut-3-enyl)amine
• 英文别名: naphthalen-1-yl(1-phenylbut-3-enyl)amine；4-(N-1-naphthyl)amino-4-phenyl-1-butene；N-(1-Phenyl-3-buten-1-yl)-1-naphthalenamine；N-(1-phenylbut-3-enyl)naphthalen-1-amine
• CAS: 241819-54-5
• 化学式: C₂₀H₁₉N
• 分子量: 273.378
• InChiKey: FNTHWAMCJIRRCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  N-α-naphthylbenzylideneimine 、 triallylaluminum 以 乙醚 为溶剂， 反应 0.5h， 以98%的产率得到naphthalene-1-yl(1-phenylbut-3-enyl)amine
  参考文献：
  名称：

  使用三烯丙基铝对羰基化合物和亚胺进行烯丙基化的新颖有效方法

  摘要：

  这是首次使用三烯丙基铝作为羰基化合物和亚胺的烯丙基化试剂的报道。迄今仅在格氏试剂的情况下才知道没有附加金属催化剂的酮亚胺的烯丙基化。三烯丙基铝是添加到醛亚胺和酮亚胺中后以优异产率提供均烯丙基胺的有用替代品。该试剂与空间刚性的酮（如金刚烷酮）反应，以98％的收率提供1-金刚烷基-3-丁烯-1-醇，证实了该试剂的显着反应性。通过使用不同的酮酸酯证明了三烯丙基铝的化学选择性。值得注意的是，三烯丙基铝是由烯丙基溴和铝金属而不是格氏试剂制得的，并且该过程操作简单，从而导致了良好的产品收率。

  DOI：

  10.1021/jo052385f

文献信息

• Titanocene(III) Chloride Mediated Radical Induced Allylation of Aldimines: Formal Synthesis of C-Linked 4′-Deoxy Aza-disaccharide
  作者：Sumit Saha、Subhas Chandra Roy

  DOI：10.1021/jo200908b

  日期：2011.9.2

  Titanocene(III) chloride (Cp2TiCl) mediated radical induced allylation of aldimines for the preparation of homoallyl amines is described. The radical was generated from the allyl bromide using Cp2TiCl as the radical source. Formal synthesis of C(4)–C(5′)-linked 4′-deoxy aza-disaccharide is demonstrated and a study toward the bicyclic skeleton of alkaloids was also accomplished. The radical initiator

  描述了氯化钛新茂（III）（Cp 2 TiCl）介导的自由基诱导的亚胺的烯丙基化，用于制备高烯丙基胺。使用Cp 2 TiCl作为自由基源，从烯丙基溴生成自由基。C（4）–C（5'）-连接的4'-脱氧氮杂-二糖的形式合成得到证明，并完成了对生物碱双环骨架的研究。自由基引发剂Cp 2 TiCl是在氩气中由市售的二茂钛二氯化物（Cp 2 TiCl 2）和Zn粉在THF中原位制备的。
• A novel series of homoallylic amines as potential antimicrobials
  作者：U. Sankappa Rai、Arun M. Isloor、Prakash Shetty、Nishitha Isloor、Mahesh Padaki、Hoong-Kun Fun

  DOI：10.1007/s00044-011-9607-3

  日期：2012.7

  An efficient catalytic three-component reaction of aldehydes, amines, and allyltributylstannate has been successfully developed to produce homoallylic amines at 25A degrees C, in excellent yields, in the presence of 1 mol% of trifluoroacetic acid an inexpensive and environmentally friendly catalyst. Newly synthesized compounds were confirmed by spectral studies. Compound 3o was characterized by single crystal X-ray analysis. All the compounds were also screened for their antimicrobial activity. Halogen-substituted compounds namely 3d, 3g, 3n, and 3o have showed excellent antibacterial activity.
• YTTERBIUM METAL/TMSCL PROMOTED REACTION OF IMINES WITH ALLYLIC BROMIDE
  作者：Weike Su、Jinghua Li、Yongmin Zhang

  DOI：10.1081/scc-100000209

  日期：——

  In the presence of chlorotrimethylsilane (TMSCl), ytterbium metal can promote the allylation of imines with allylic bromide to give the corresponding homoallylamines in satisfactory yields in THF under mild conditions.
• Novel and Efficient Method for the Allylation of Carbonyl Compounds and Imines Using Triallylaluminum
  作者：Kao-Hsien Shen、Ching-Fa Yao

  DOI：10.1021/jo052385f

  日期：2006.5.1

  triallylaluminum as a reagent for the allylation of carbonyl compounds and imines. The allylation of ketimines without additional metal catalyst is known so far only in the case of the Grignard reagent. Triallylaluminum is a useful alternative to provide the homoallylic amines in excellent yield upon addition to aldimines and ketimines. The significant reactivity of this reagent was confirmed by its

  这是首次使用三烯丙基铝作为羰基化合物和亚胺的烯丙基化试剂的报道。迄今仅在格氏试剂的情况下才知道没有附加金属催化剂的酮亚胺的烯丙基化。三烯丙基铝是添加到醛亚胺和酮亚胺中后以优异产率提供均烯丙基胺的有用替代品。该试剂与空间刚性的酮（如金刚烷酮）反应，以98％的收率提供1-金刚烷基-3-丁烯-1-醇，证实了该试剂的显着反应性。通过使用不同的酮酸酯证明了三烯丙基铝的化学选择性。值得注意的是，三烯丙基铝是由烯丙基溴和铝金属而不是格氏试剂制得的，并且该过程操作简单，从而导致了良好的产品收率。