2-phenyl-1-(1-pyrenyl)ethanone | 60714-31-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 2-phenyl-1-(1-pyrenyl)ethanone
• 英文别名: 2-phenyl-1-pyren-1-yl-ethanone；2-Phenyl-1-pyren-1-yl-aethanon；2-Phenyl-1-pyren-1-ylethanone
• CAS: 60714-31-0
• 化学式: C₂₄H₁₆O
• 分子量: 320.39
• InChiKey: BYUVBDGDTZASFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-phenyl-1-(1-pyrenyl)ethanone 在 lithium aluminium tetrahydride 作用下， 生成 2-Phenyl-1-pyren-1-yl-ethanol
  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：

  芘 、 苯乙酰氯 在 二硫化碳 、 三氯化铝 作用下， 生成 2-phenyl-1-(1-pyrenyl)ethanone
  参考文献：
  名称：

  Buu-Hoi; Royer, Bulletin de la Societe Chimique de France, 1946, p. 659

  摘要：

  DOI：

文献信息

• Direct Synthesis of Arylketones by Nickel-Catalyzed Addition of Arylboronic Acids to Nitriles
  作者：Ying-Chieh Wong、Kanniyappan Parthasarathy、Chien-Hong Cheng

  DOI：10.1021/ol1003252

  日期：2010.4.16

  A convenient and efficient method for the synthesis of various arylketones by nickel-catalyzed addition of arylboronic acids to nitriles is described. A catalytic cycle involving Ni(II) species as the catalytic intermediates is proposed to account for the present catalytic reaction.

  描述了一种通过镍催化将芳基硼酸加成到腈中来合成各种芳基酮的方便有效的方法。提出了涉及Ni（II）物质作为催化中间体的催化循环以解决当前的催化反应。
• Buu-Hoi et al., Journal of the Chemical Society, 1951, p. 1381,1384
  作者：Buu-Hoi et al.

  DOI：——

  日期：——
• GERASIMENKO YU. E.; DIDENKO S. I., ZH. ORGAN. XIMII <ZORK-AE>, 1976, 12, HO 7, 1546-1553
  作者：GERASIMENKO YU. E.、 DIDENKO S. I.

  DOI：——

  日期：——