6,7-dihydro-5H-benzo[c][1,2,3]triazolo[1,5-a]azepine | 1429337-85-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6,7-dihydro-5H-benzo[c][1,2,3]triazolo[1,5-a]azepine
• 英文别名: 6,7-dihydro-5H-triazolo[5,1-a][2]benzazepine
• CAS: 1429337-85-8
• 化学式: C₁₁H₁₁N₃
• 分子量: 185.228
• InChiKey: DBZATMPMYNNQPD-UHFFFAOYSA-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：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(2-iodophenyl)propan-1-ol 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium azide 、 四丁基溴化铵 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 6,7-dihydro-5H-benzo[c][1,2,3]triazolo[1,5-a]azepine
  参考文献：
  名称：

  Facile Synthesis of [1,2,3]-Triazole-Fused Isoindolines, Tetrahydroisoquino­lines, Benzoazepines and Benzoazocines by Palladium-Copper Catalysed Heterocyclisation­

  摘要：

  An elegant method for the synthesis of 1,2,3-triazoles fused with five-, six-, seven- and eight-membered benzoheterocycles, including isoindoline, tetrahydroisoquinoline, benzoazepine and benzoazocine, has been developed via palladium-copper catalysed reactions in one-pot. The broad scope of this reaction was illustrated by effecting bis-heteroannulations, synthesis of uracil derivatives of biological interest, and employment of acetylene gas as an inexpensive substrate. The reactions are experimentally simple and utilise easily accessible substrates of different types.

  DOI：

  10.1055/s-0032-1316839

文献信息

• Expedient Access to 2-Benzazepines by Palladium-Catalyzed C−H Activation: Identification of a Unique Hsp90 Inhibitor Scaffold
  作者：Matteo Virelli、Elisabetta Moroni、Giorgio Colombo、Lorenzo Fiengo、Alessio Porta、Lutz Ackermann、Giuseppe Zanoni

  DOI：10.1002/chem.201804244

  日期：2018.11.7

  Bioactive 2‐benzazepines were accessed in an atom‐ and step‐economical manner through a versatile palladium‐catalyzed C−H activation strategy. The C−H arylation required low catalyst loading and a mild base, which was reflected by a broad scope and high functional‐group tolerance. The benzotriazolodiazepinones were identified as new heat shock protein 90 (Hsp90) inhibiting lead compounds, with considerable

  生物活性的2-苯并ze庚因是通过通用的钯催化的CH活化方法以原子经济和分步经济的方式获得的。CH芳基化反应需要低的催化剂负载量和适度的碱，这反映在宽范围和高官能团耐受性上。苯并三唑并二氮杂吡啶酮被鉴定为新的抑制热激蛋白90（Hsp90）的先导化合物，在抗癌应用中具有相当大的潜力。