ethyl 2-azido-3-(2-bromophenyl)acrylate | 1206626-34-7

• 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: ethyl 2-azido-3-(2-bromophenyl)acrylate
• 英文别名: Ethyl 2-azido-3-(2-bromophenyl)prop-2-enoate
• CAS: 1206626-34-7
• 化学式: C₁₁H₁₀BrN₃O₂
• 分子量: 296.123
• InChiKey: LRZJHRYNFMFHGN-UHFFFAOYSA-N

物化性质

• 熔点：
  48-50 °C

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-azido-3-(2-bromophenyl)acrylate 在 氯化锆(IV) 、 silver nitrate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以63%的产率得到4-溴吲哚-2-甲酸乙酯
  参考文献：
  名称：

  ZrCl₄-promoted facile synthesis of indole derivatives

  摘要：

  锆（IV）氯化物有效地激活芳基叠氮丙烯酸酯中的氮（N2）挤出，随后进行环化反应，以中等至良好的产率提供所需的吲哚产物。

  DOI：

  10.1039/c4ra02158d
• 作为产物：
  描述：

  叠氮乙酸乙酯 、 邻溴苯甲醛 生成 ethyl 2-azido-3-(2-bromophenyl)acrylate
  参考文献：
  名称：

  Synthesis of 2,3,4-trisubstituted pyrroles via a facile reaction of vinyl azides and tosylmethyl isocyanide

  摘要：

  从对甲苯甲基异氰酸酯（TOSMIC）和容易合成的乙烯基叠氮化合物中合成多取代吡咯的简便方法已经开发出来。在碱的存在下，在温和条件下进行反应。2-对甲苯基取代的吡咯以中等至良好的收率得到。此外，还开发了一种碱引发的一锅法吡咯合成方法，使用羧醛、乙酸叠氮乙酯和TOSMIC。

  DOI：

  10.1139/v11-150

文献信息

• Manganese(II)-Mediated Domino Annulation Reaction of Vinyl Azides and 4-Hydroxycoumarin: A Stereoselective Synthesis of Spirobenzofuranone-lactams
  作者：Shanshan Guo、Binhui Chen、Donghong Zhao、Wenteng Chen、Guolin Zhang

  DOI：10.1002/adsc.201600423

  日期：2016.10.6

  A manganese(II) acetate‐catalyzed domino reaction of vinyl azides and 4‐hydroxycoumarin has been developed for the synthesis of polyfunctionalized spirofuranone‐lactams. A wide range of vinyl azides are capable of providing the desired spirofuranone‐lactams in good to excellent yields. The reaction was achieved via thermal decomposition of vinyl azides to 2H‐azirines, followed by an intramolecular

  已开发出锰（II）乙酸锰催化的叠氮化物和4-羟基香豆素的多米诺反应，用于合成多官能化的螺呋喃酮-内酰胺。各种各样的乙烯基叠氮化物能够以优异的产率提供所需的螺呋喃酮-内酰胺。该反应是通过将乙烯基叠氮化物热分解为2 H-叠氮基，然后进行分子内亲核攻击和立体选择性环化而实现的。温和的反应条件和简便的操作使该反应对于合成螺呋喃酮-内酰胺具有优势。
• Mn(II)-catalyzed synthesis of benzo[f]indole-4,9-diones via vinyl azides and 2-hydroxynaphthoquinone
  作者：Shanshan Guo、Binhui Chen、Xiao Guo、Guolin Zhang、Yongping Yu

  DOI：10.1016/j.tet.2015.08.067

  日期：2015.12

  A novel, convenient and economical protocol to prepare polyfunctionalized benzo[f]indole-4,9-diones catalyzed by Mn(II) acetate from vinyl azides and 2-hydroxynaphthoquinone has been achieved. This reaction proceeded in good to excellent yields for a wide range of vinyl azides, and a possible mechanism has also been proposed. (C) 2015 Published by Elsevier Ltd.
• Copper-catalyzed tandem synthesis of [1,2,3]triazolo[5,1-a]isoquinolines and their transformation to 1,3-disubstituted isoquinolines
  作者：Yuan-Yuan Hu、Jie Hu、Xiang-Chuan Wang、Li-Na Guo、Xing-Zhong Shu、Yan-Ning Niu、Yong-Min Liang

  DOI：10.1016/j.tet.2009.11.043

  日期：2010.1

  2-Azido-3-(2-iodophenyl)acrylates react with terminal alkynes in the presence of a copper(II) catalyst without ligands to give a wide range of [1,2,3]triazolo[5,1-a]isoquinolines in good yields. These compounds favor expulsion of N-2 in refluxed acetic acid to form 1,3-disubstituted isoquinolines. The procedure is simple, economical, and efficient. (C) 2009 Elsevier Ltd. All rights reserved.
• Domino Approach for the Synthesis of Pyrrolo[1,2-α]pyrazine from Vinyl Azides
  作者：Wenteng Chen、Miao Hu、Jianwei Wu、Hongbin Zou、Yongping Yu

  DOI：10.1021/ol101538x

  日期：2010.9.3

  A domino synthesis of pyrrolo[1,2-alpha]pyrazine from 1H-2-pyrrolecarbaldehyde and readily synthesized vinyl azides was developed. This reaction proceeded under relatively mild conditions in the presence of base. Additionally, a possible mechanism for the entire sequence is proposed.