(E)-methyl 2-(azidomethyl)-5-(4-fluorophenyl)pent-2-en-4-ynoate | 1228932-04-4

• 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: (E)-methyl 2-(azidomethyl)-5-(4-fluorophenyl)pent-2-en-4-ynoate
• CAS: 1228932-04-4
• 化学式: C₁₃H₁₀FN₃O₂
• 分子量: 259.24
• InChiKey: SYPULLXHLUTIJT-NYYWCZLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  75.06
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-methyl 2-(azidomethyl)-5-(4-fluorophenyl)pent-2-en-4-ynoate 以 甲苯 为溶剂， 反应 1.0h， 以88%的产率得到methyl 3-(4-fluorophenyl)-6H-pyrrolo[1,2-c][1,2,3]triazole-5-carboxylate
  参考文献：
  名称：

  3,5-Disubstituted 6H-pyrrolo[1,2-c][1,2,3]triazoles from Morita–Baylis–Hillman adducts of propargyl aldehydes

  摘要：

  A simple method for synthesizing several 6H-pyrrolo[1,2-c][1,2,3]triazole derivatives having a methoxy carbonyl or an acetyl group at C-5 position and 7,8-dihydro-4H-[1,2,3]triazolo[1,5-a]indol-5(6H)-ones via an intramolecular 1,3-dipolar cycloaddition reaction of azido enynes, which were readily obtained from the Morita-Baylis-Hillman acetates of propargyl aldehydes with sodium azide, has been developed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.017
• 作为产物：
  描述：

  3-(4-氟苯基)-2-丙炔醛 在 三乙烯二胺 、 4-二甲氨基吡啶 、 sodium azide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 4.5h， 生成 (E)-methyl 2-(azidomethyl)-5-(4-fluorophenyl)pent-2-en-4-ynoate
  参考文献：
  名称：

  铜催化烯丙基叠氮化物的分子内硫属元素胺化：5-硒基/亚磺酰基烟酸酯的合成

  摘要：

  已经描述了用于合成5-硒烯基/亚磺酰基烟酸酯的新方法，该方法涉及铜催化的烯丙基叠氮化物与二有机基-二卤代羰基化的有机硫属酰基氮杂-环化。该方法在一锅中通过区域选择性分子内硫属元素铝化作用使炔烃双官能化，从而以良好或优异的产率提供取代的5-硫属元素酰基烟酸酯。所得烟酸酯提供了它们的氧化物，砜和酸衍生物的途径。

  DOI：

  10.1021/acs.orglett.8b03695

文献信息

• Cu(I)-Catalyzed Aminative Aza-Annulation of Enynyl Azide using <i>N</i>-Fluorobenzenesulfonimide: Synthesis of 5-Aminonicotinates
  作者：Chada Raji Reddy、Santosh Kumar Prajapti、Ravi Ranjan

  DOI：10.1021/acs.orglett.8b01228

  日期：2018.5.18

  An unprecedented copper-catalyzed aminative aza-annulation of enynyl azide using commercially available N-fluorobenzenesulfonhnide (NFSI) as an amination reagent is described. The reaction proceeds via regioselective inter-/intramolecular diamination, incorporating one nitrogen from the NFSI and the other from the azide, to provide amino substituted nicotinate derivatives in a single step with moderate to high yield. This method represents an efficient way to access diverse aminonicotinates through direct C-N bond-coupling processes.
• 3,5-Disubstituted 6H-pyrrolo[1,2-c][1,2,3]triazoles from Morita–Baylis–Hillman adducts of propargyl aldehydes
  作者：Sun Pil Park、Sang-Hyun Ahn、Kee-Jung Lee

  DOI：10.1016/j.tet.2010.03.017

  日期：2010.5

  A simple method for synthesizing several 6H-pyrrolo[1,2-c][1,2,3]triazole derivatives having a methoxy carbonyl or an acetyl group at C-5 position and 7,8-dihydro-4H-[1,2,3]triazolo[1,5-a]indol-5(6H)-ones via an intramolecular 1,3-dipolar cycloaddition reaction of azido enynes, which were readily obtained from the Morita-Baylis-Hillman acetates of propargyl aldehydes with sodium azide, has been developed. (C) 2010 Elsevier Ltd. All rights reserved.
• Copper-Catalyzed Intramolecular Chalcogenoamination of Enynyl Azides: Synthesis of 5-Selenyl/Sulfenyl Nicotinates
  作者：Chada Raji Reddy、Ravi Ranjan、Santosh Kumar Prajapti

  DOI：10.1021/acs.orglett.8b03695

  日期：2019.2.1

  methodology for the synthesis of 5-selenyl/sulfenyl nicotinates involving copper-catalyzed organochalcogenyl aza-annulation of enynyl azide with diorganyl-dichalcogenides has been described. This method offers difunctionalization of alkynes via regioselective intramolecular chalcogenoamination in one pot to provide substituted 5-chalcogenyl nicotinates in good to excellent yields. The resulting nicotinates

  已经描述了用于合成5-硒烯基/亚磺酰基烟酸酯的新方法，该方法涉及铜催化的烯丙基叠氮化物与二有机基-二卤代羰基化的有机硫属酰基氮杂-环化。该方法在一锅中通过区域选择性分子内硫属元素铝化作用使炔烃双官能化，从而以良好或优异的产率提供取代的5-硫属元素酰基烟酸酯。所得烟酸酯提供了它们的氧化物，砜和酸衍生物的途径。