(E)-N-(3-(4-methoxyphenyl)allyl)formamide | 107960-67-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-N-(3-(4-methoxyphenyl)allyl)formamide
• 英文别名: (E)-N-formyl-p-methoxycinnamylamine；N-[(E)-3-(4-methoxyphenyl)prop-2-enyl]formamide
• CAS: 107960-67-8
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: DUSDKZRZOFQJPR-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-N-(3-(4-methoxyphenyl)allyl)formamide 在 吡啶 、 四氧化锇 作用下， 反应 20.0h， 以41 mg的产率得到threo-2-hydroxy-3-(formylamino)-1-(4-methoxyphenyl)propanol
  参考文献：
  名称：

  Revised structure of bursatellin

  摘要：

  DOI：

  10.1021/jo00387a037
• 作为产物：
  描述：

  4-甲氧基烟腈 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.25h， 生成 (E)-N-(3-(4-methoxyphenyl)allyl)formamide
  参考文献：
  名称：

  Revised structure of bursatellin

  摘要：

  DOI：

  10.1021/jo00387a037

文献信息

• Palladium-Catalyzed Synthesis of Allylic Ureas via an Isocyanate Intermediate
  作者：Lucien P. Jay、Timothy J. Barker

  DOI：10.1002/ejoc.201600149

  日期：2016.4

  A palladium-catalyzed coupling of allylic carbonates with trimethylsilylisocyanate to provide allylic isocyanates is reported. Amines are added in a second step to yield allylic ureas in this one-pot procedure. Use of a bidentate phosphine ligand with a large bite angle was found to be important in this transformation. The scope of allylic carbonates has been examined, as well as amines compatible

  报道了烯丙基碳酸酯与三甲基甲硅烷基异氰酸酯的钯催化偶联以提供烯丙基异氰酸酯。在此一锅法中，在第二步中添加胺以产生烯丙基脲。发现使用具有大咬合角的双齿膦配体在这种转变中很重要。已检查烯丙基碳酸酯的范围，以及与这些反应条件相容的胺。
• Substrate-Directable Heck Reactions with Arenediazonium Salts. The Regio- and Stereoselective Arylation of Allylamine Derivatives and Applications in the Synthesis of Naftifine and Abamines
  作者：Patrícia Prediger、Laís Ferreira Barbosa、Yves Génisson、Carlos Roque Duarte Correia

  DOI：10.1021/jo201105z

  日期：2011.10.7

  The palladium-catalyzed, substrate-directable Heck-Matsuda reaction of allylamine derivatives with arenediazonium salts is reported. The reaction proceeds under mild conditions, with excellent regio- and stereochemical control as a function of coordinating groups present in the allylamine substrate. The distance between the olefin moiety and the carbonylic system seems to play a key role regarding the regiocontrol. The method presents itself as robust, as simple to carry out, and with wide synthetic scope concerning the allylic substrates and the type of arenediazonium employed. The synthetic potential of the method is illustrated by the short total syntheses of the bioactive compounds naftifine, abamine, and abamine SG.