(E)-methyl 2-(aminomethyl)-3-(4-fluorophenyl)acrylate | 1009375-48-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-methyl 2-(aminomethyl)-3-(4-fluorophenyl)acrylate
• 英文别名: methyl (E)-2-(aminomethyl)-3-(4-fluorophenyl)prop-2-enoate
• CAS: 1009375-48-7
• 化学式: C₁₁H₁₂FNO₂
• 分子量: 209.22
• InChiKey: QDCCSZIJZNBXMX-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 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：
  52.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-methyl 2-(aminomethyl)-3-(4-fluorophenyl)acrylate 在 碘 、 potassium carbonate 作用下， 以 氯仿 为溶剂， 反应 0.58h， 以80%的产率得到methyl 7-fluoroquinoline-3-carboxylate
  参考文献：
  名称：

  Iodine-Mediated Intramolecular Electrophilic Aromatic Cyclization in Allylamines: A General Route to Synthesis of Quinolines, Pyrazolo[4,3-b]pyridines, and Thieno[3,2-b]pyridines

  摘要：

  An unprecedented synthesis of aromatic ring annulated pyridines from suitably substituted primary allylamines via intramolecular electrophilic aromatic cyclization mediated by molecular iodine under mild conditions is described.

  DOI：

  10.1021/ol303109m
• 作为产物：
  描述：

  methyl 3-(4-fluorophenyl)-3-hydroxy-2-methylenepropanoate 在 吡啶 、 甲醇 、 氨 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (E)-methyl 2-(aminomethyl)-3-(4-fluorophenyl)acrylate
  参考文献：
  名称：

  Iodine-Mediated Intramolecular Electrophilic Aromatic Cyclization in Allylamines: A General Route to Synthesis of Quinolines, Pyrazolo[4,3-b]pyridines, and Thieno[3,2-b]pyridines

  摘要：

  An unprecedented synthesis of aromatic ring annulated pyridines from suitably substituted primary allylamines via intramolecular electrophilic aromatic cyclization mediated by molecular iodine under mild conditions is described.

  DOI：

  10.1021/ol303109m

文献信息

• Application of Primary Allylamine Derivatives of Baylis-Hillman Adducts to Heterocyclic Synthesis: Generation of 5-Benzyl-4(3<i>H</i>)-pyrimidinones and 2-Benzylidene-2,3-dihydropyrrolizin-1-ones
  作者：Sanjay Batra、Somnath Nag、Sudharshan Madapa

  DOI：10.1055/s-2007-990929

  日期：2008.1

  The applications of the primary allyl amines afforded by the acetyl derivative of Baylis-Hillman adducts of acrylate for the synthesis of heterocycles using robust reactions are described. In the first strategy a one-pot synthesis of 5-benzyl-4(3H)- pyrimidinones have been achieved via N-formylation of the amines in the presence of neat formamide followed by ammonium formate-mediated cyclization. These

  描述了由丙烯酸酯的 Baylis-Hillman 加合物的乙酰基衍生物提供的伯烯丙胺在使用稳健反应合成杂环中的应用。在第一种策略中，5-苄基-4(3H)-嘧啶酮的单锅合成是通过在纯甲酰胺存在下胺的 N-甲酰化，然后是甲酸铵介导的环化来实现的。这些嘧啶酮已被证明是 4-吡啶胺衍生物的优良前体。在第二种策略中，2-亚苄基-2,3-二氢吡咯嗪-1-酮的合成是通过用二甲氧基呋喃处理烯丙胺，然后进行皂化和PPA介导的分子内环化来完成的。
• Isonitriles from the Baylis–Hillman adducts of acrylates: viable precursor to tetrazolo-fused diazepinones via post-Ugi cyclization
  作者：Maloy Nayak、Sanjay Batra

  DOI：10.1016/j.tetlet.2009.11.051

  日期：2010.1

  Stereocontrolled synthesis of substituted isonitriles from the Baylis-Hillman adducts of acrylates has been developed. Ugi reaction of these isonitriles with TMSN3, aliphatic amines, and aldehydes or ketone affords 1-substituted tetrazoles which have been demonstrated to be suitable substrates for producing tetrazolo-fused diazepinones. (C) 2009 Elsevier Ltd. All rights reserved.
• Iodine-Mediated Intramolecular Electrophilic Aromatic Cyclization in Allylamines: A General Route to Synthesis of Quinolines, Pyrazolo[4,3-<i>b</i>]pyridines, and Thieno[3,2-<i>b</i>]pyridines
  作者：Harikrishna Batchu、Soumya Bhattacharyya、Sanjay Batra

  DOI：10.1021/ol303109m

  日期：2012.12.21

  An unprecedented synthesis of aromatic ring annulated pyridines from suitably substituted primary allylamines via intramolecular electrophilic aromatic cyclization mediated by molecular iodine under mild conditions is described.