3'-(methylcarbonyl)acenaphtho<4,5-e>triazole | 133578-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3'-(methylcarbonyl)acenaphtho<4,5-e>triazole
• 英文别名: 1-(3,4,5-triazatetracyclo[6.6.1.02,6.011,15]pentadeca-1(14),2(6),3,7,11(15),12-hexaen-5-yl)ethanone
• CAS: 133578-51-5
• 化学式: C₁₄H₁₁N₃O
• 分子量: 237.261
• InChiKey: HMSOUHMJOCVFFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  47.78
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1'-(methylcarbonyl)acenaphtho<4,5-e>triazole 在 吡啶 、 硫酸 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 3'-(methylcarbonyl)acenaphtho<4,5-e>triazole
  参考文献：
  名称：

  Sterically congested polycyclic aromatic hydrocarbons with nonoptimal geometries. 4,5-Didehydroacenaphthene as a precursor for the synthesis of 7,14-diphenyl-8,9-(1',8'-naphthenylene)acephenanthrene

  摘要：

  A multistep synthetic route for the synthesis of the reactive intermediate 4,5-didehydroacenaphthene (15) is described. A mixture of N-1-, N-2-, and N-3-aminoacenaphtho[4,5-e]triazoles is produced, which is oxidized by lead tetraacetate (LTA) to the corresponding aryne. The N-2-triazole is oxidized by LTA to 7-cyano-1-(cyanomethylene)indan (18), whose structure was verified by X-ray analysis. Intermediate 15 was trapped by 7,9-diphenyl-8H-cyclopenta[a]acenaphthylen-8-one (acecyclone) to produce the congested hydrocarbon 7,14-diphenyl-8,9-(1',8'-naphthenylene)acephenanthrene (20). There is a small deviation from planarity for 20, and this is modeled by MMX calculations and verified by X-ray crystallographic analysis of the structure.

  DOI：

  10.1021/jo00010a010