1-dodecanoyl-1-pyrene | 78751-52-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1-dodecanoyl-1-pyrene
• CAS: 78751-52-7
• 化学式: C₂₈H₃₂O
• 分子量: 384.561
• InChiKey: HBDQFKMLMODHPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.69
• 重原子数：
  29.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-dodecanoyl-1-pyrene 在 lithium aluminium tetrahydride 作用下， 生成 1-Pyren-1-yldodecan-1-ol
  参考文献：
  名称：

  Charge Delocalization Pathways in Persistent 1-Pyrenyl-, 4-Pyrenyl-, and 2-Pyrenylmethylcarbenium Ions as Models of PAH−Epoxide Ring Opening:  NMR Studies in Superacids and AM1 Calculations

  摘要：

  The relative stability, magnitude, and mode of charge delocalization into the pyrene moiety (Py) were evaluated for a series of tertiary and secondary 1-pyrenylmethylcarbenium ions PyC+R1R2 and PyC+R3H (with R-1 = R-2 = Me and Ph; R-3 = Me, Ph, CH2Ph, and (CH2)(10)Me), 4-pyrenylmethylcarbenium ions (with R-1 = R-2 = Me; R-3 = Me and Ph), and 2-pyrenylmethylcarbenium ions (with R-1 = R-2 = Me). The carbocations were generated from the corresponding carbinols by protonation with FSO3H/SO2ClF. The primary 1-pyrenyl- and 2-pyrenylmethyl cations could not be generated by ionization of their primary alcohols. Within the tertiary and the secondary carbocations, pi-charge delocalization into the pyrene moiety and the pyrenium ion character of the resulting carbocations increase in the order: 1-pyrenyl (alpha) > 4-pyrenyl (alpha beta) > 2-pyrenyl (beta). The NMR characteristics of the resulting ions are discussed and compared. The connection between charge delocalization/ stability in the regioisomeric pyrenylmethyl carbocations and the magnitude of carcinogenic activity in the benzannelated pyrenes, for which the bay-region diol-epoxides are the ultimate carcinogens, are discussed.

  DOI：

  10.1021/jo9707343
• 作为产物：
  描述：

  月桂酸 、 芘 以70%的产率得到1-dodecanoyl-1-pyrene
  参考文献：
  名称：

  衍生的新型一组分和二组分有机胶凝剂。

  摘要：

  合成了一类新的烷基链附加的derivatives衍生物4-14，并评估了它们的胶凝能力。根据连接基团的性质，这些化合物在存在或不存在受体分子2,4,7-三硝基芴酮（TNF）的条件下会胶凝许多有机溶剂。具有酯，醚或烷基键的化合物通过与TNF的电荷转移相互作用而胶凝许多羟基和烃类溶剂，而具有酰胺，氨基甲酸酯和尿素接头的化合物则通过多种溶剂在各自的溶剂中自行形成凝胶π-π堆积和氢键相互作用。氨基甲酸酯（S）-12的X射线晶体结构显示出氢键和堆积特征，如模型所暗示。

  DOI：

  10.1002/chem.200204459