4-amino-5-acetamidoacenaphthene | 35341-35-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-amino-5-acetamidoacenaphthene
• 英文别名: 5-Acetamido-4-aminoacenaphthen；N-(4-Aminoacenaphthen-5-YL)acetamide；N-(4-amino-1,2-dihydroacenaphthylen-5-yl)acetamide
• CAS: 35341-35-6
• 化学式: C₁₄H₁₄N₂O
• 分子量: 226.278
• InChiKey: XJYQHAQIHJMZDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-amino-5-acetamidoacenaphthene 在 盐酸 、 硫酸 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 2.5h， 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
• 作为产物：
  描述：

  N-（1,2-dihydroacenaphthylen-5-基）乙酰胺 在 palladium on activated charcoal 氢气 、 copper(II) nitrate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、413.69 kPa 条件下， 反应 7.0h， 生成 4-amino-5-acetamidoacenaphthene
  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

• 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.