5-dimethylaminoacenaphthylene | 4536-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 吖萘类
• 英文名称: 5-dimethylaminoacenaphthylene
• 英文别名: N,N-dimethylacenaphthylen-5-amine
• CAS: 4536-95-2
• 化学式: C₁₄H₁₃N
• 分子量: 195.264
• InChiKey: NLMHZPQHGAHVGN-UHFFFAOYSA-N

物化性质

• 沸点：
  332.6±21.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,6-二苯基-1,2,4,5-四嗪 、 5-dimethylaminoacenaphthylene 以 苯 为溶剂， 反应 90.0h， 以74%的产率得到3-dimethylamino-7,10-diphenyl-8,9-diazafluoranthene
  参考文献：
  名称：

  摘要：

  5,6-Bis(dimethylamino)acenaphthylene is readily involved in [4+2] cycloaddition reactions with symm-tetrazine derivatives to form new "proton sponges" with the diazafluoranthene skeleton. Under analogous condition, 1,8-bis(dimethylamino)-4-vinylnaphthalene gave 4-pyridazinyl derivatives. The relative reactivities of 5,6-bis(dimethylamino)acenaphthylene, 1,8-bis(dimethylamino)-4-vinylnaphthatene. 5-dimethylamitioacenaphthylene, and acenaphthylene in the reactions with 3.6-diphenyl-symm-tetrazine are in a ratio of 32 : 17 : 14 : 1. The site of protonation of 3,4-bis(dimethylamino)-7,10-diphenyl-8,9-diazafluoranthene is controlled by the basicity of the solvent. The reaction in acetonitrile afforded the cation stabilized by an intramolecular hydrogen bond, whereas the reaction in dimethyl suffoxide gave rise to the resonance-stabilized cation. 6,7-Bis(dimethylamino)phenalen-1-one was protonated only at the carbonyl group.

  DOI：

  10.1023/a:1022429322461
• 作为产物：
  描述：

  5-dimethylaminoacenaphthene 在 四氯苯醌 作用下， 以 苯 为溶剂， 反应 0.5h， 以44%的产率得到5-dimethylaminoacenaphthylene
  参考文献：
  名称：

  摘要：

  5,6-Bis(dimethylamino)acenaphthylene is readily involved in [4+2] cycloaddition reactions with symm-tetrazine derivatives to form new "proton sponges" with the diazafluoranthene skeleton. Under analogous condition, 1,8-bis(dimethylamino)-4-vinylnaphthalene gave 4-pyridazinyl derivatives. The relative reactivities of 5,6-bis(dimethylamino)acenaphthylene, 1,8-bis(dimethylamino)-4-vinylnaphthatene. 5-dimethylamitioacenaphthylene, and acenaphthylene in the reactions with 3.6-diphenyl-symm-tetrazine are in a ratio of 32 : 17 : 14 : 1. The site of protonation of 3,4-bis(dimethylamino)-7,10-diphenyl-8,9-diazafluoranthene is controlled by the basicity of the solvent. The reaction in acetonitrile afforded the cation stabilized by an intramolecular hydrogen bond, whereas the reaction in dimethyl suffoxide gave rise to the resonance-stabilized cation. 6,7-Bis(dimethylamino)phenalen-1-one was protonated only at the carbonyl group.

  DOI：

  10.1023/a:1022429322461