Ethyl 3-(2-azidophenyl)prop-2-enoate | 1422541-80-7

• 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 3-(2-azidophenyl)prop-2-enoate
• 英文别名: ethyl 3-(2-azidophenyl)prop-2-enoate
• CAS: 1422541-80-7
• 化学式: C₁₁H₁₁N₃O₂
• 分子量: 217.227
• InChiKey: BCUZBUIXWDHZAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 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 3-(2-azidophenyl)prop-2-enoate 以 乙腈 为溶剂， 反应 1.5h， 以68%的产率得到吲哚-2-羧酸乙酯
  参考文献：
  名称：

  邻-叠氮基肉桂酰基衍生物的光化学：溶剂控制下 2-酰化吲哚和 2-取代喹啉的简便和模块化合成

  摘要：

  评估邻-叠氮基肉桂酰基化合物的光促进潜力用于杂环合成。根据溶剂的性质，在质子惰性条件下获得 2-酰化吲哚，而使用质子介质产生 2-取代喹啉。这种不含金属的方法的合成意义在于，通过简单地改变溶剂，反应结果可以针对不同的关键杂环支架。

  DOI：

  10.1055/s-0036-1590861

文献信息

• Synthesis, Fungicidal Activity, and Sterol 14α-Demethylase Binding Interaction of 2-Azolyl-3,4-dihydroquinazolines on Penicillium digitatum
  作者：Wen-Jin Li、Qian Li、De-Li Liu、Ming-Wu Ding

  DOI：10.1021/jf305355u

  日期：2013.2.20

  A series of new 2-azolyl-3,4-dihydroquinazolines 6 was synthesized by direct cyclization of imidazole or 1,2,4-triazole with carbodiimides 4, which were obtained from aza-Wittig reaction of iminophosphorane 3 with isocyanate. The preliminary bioassay results demonstrated that most of the 2-imidazolyl-3,4-dihydroquinazolines 6a-6i exhibited good to significant fungicidal activity against Penicillium digitatum, whereas 2-triazolyl-3,4-dihydroquinazolines 6j-6t exhibited low fungicidal activity. Some of the 2-imidazolyl-3,4-dihydroquinazolines 6a-6i also exhibited strong binding interaction with the cytochrome P450-dependent sterol 14 alpha-demethylase (CYP51). For example, compound 6e showed the best fungicidal activity against P. digitatum with IC50 = 4.14 mu g/mL and the best CYP51 binding activity with K-d = 0.34 mu g/mL, both superior to those of the agricultural fungicide triadimefon.
• Photochemistry of ortho-Azidocinnamoyl Derivatives: Facile and Modular Synthesis of 2-Acylated Indoles and 2-Substituted Quinolines under Solvent Control
  作者：S. Chassaing、S. Chaabouni、N. Pinkerton、S. Abid、C. Galaup

  DOI：10.1055/s-0036-1590861

  日期：2017.12

  The light-promoted potential of ortho -azidocinnamoyl compounds is evaluated for heterocycle synthesis. Depending on the nature of the solvent, 2-acylated indoles were obtained under aprotic conditions, whereas the use of a protic medium led to 2-substituted quinolines. The synthetic significance of this metal-free method is that, by simply changing the solvent, the reaction outcome can be directed

  评估邻-叠氮基肉桂酰基化合物的光促进潜力用于杂环合成。根据溶剂的性质，在质子惰性条件下获得 2-酰化吲哚，而使用质子介质产生 2-取代喹啉。这种不含金属的方法的合成意义在于，通过简单地改变溶剂，反应结果可以针对不同的关键杂环支架。