acenaphtho<4,5-e>triazole | 116082-62-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: acenaphtho<4,5-e>triazole
• 英文别名: 5,9-dihydro-4H-acenaphtho[4,5-d][1,2,3]triazole；5,9-Dihydro-4H-acenaphtho[4,5-d][1,2,3]triazol；3,4,5-Triazatetracyclo[6.6.1.02,6.011,15]pentadeca-1(14),2,5,7,11(15),12-hexaene
• CAS: 116082-62-3
• 化学式: C₁₂H₉N₃
• 分子量: 195.224
• InChiKey: JZZRSEYODLBDPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  acenaphtho<4,5-e>triazole 在 lead(IV) acetate 、 氢氧化钾 、 hydroxylamine-O-sulfonic acid 作用下， 生成 7-cyano-1-(cyanomethylene)indan
  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
• 作为产物：
  描述：

  N-（1,2-dihydroacenaphthylen-5-基）乙酰胺 在 palladium on activated charcoal 盐酸 、 硫酸 、 氢气 、 copper(II) nitrate 、 溶剂黄146 、 sodium nitrite 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 4.0~20.0 ℃ 、413.69 kPa 条件下， 反应 9.5h， 生成 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

文献信息

• Acenaphthene Chemistry. III.¹ The Preparation and Reactions of 4,5-Acenaphthenequinonedibenzenesulfonimide²
  作者：Henry J. Richter、Berton C. Weberg

  DOI：10.1021/ja01556a068

  日期：1958.12
• 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
  作者：Benjamin F. Plummer、Steven R. Russell、W. Gregory Reese、William H. Watson、Mariusz Krawiec

  DOI：10.1021/jo00010a010

  日期：1991.5

  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.