1-萘基烯酮 | 67279-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-萘基烯酮
• 英文名称: 1-naphthylketene
• 英文别名: 1-Naphthyl-keten
• CAS: 67279-06-5
• 化学式: C₁₂H₈O
• 分子量: 168.195
• InChiKey: QGKVZGXBYGLUHR-UHFFFAOYSA-N

物化性质

• 沸点：
  284.8±10.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1-萘基烯酮 在 sodium hydroxide 作用下， 生成 1-萘乙酸
  参考文献：
  名称：

  Solvent isotope effect on the hydroxide-ion-catalyzed hydration of ketenes in aqueous solution

  摘要：

  Five ketenes, phenyl(ethyl)ketene, phenyl(methylthio)ketene, diphenylketene, pentafluorophenylketene, and 1-naphthylketene, were generated flash photolytically and solvent isotope effects (H2O vs. D2O) on their hydroxide-ion-catalyzed hydration in aqueous solution were determined. The values obtained are all weakly inverse and closely similar (k(HO)/k(DO) = 0.76-0.97), as expected for these fast, hydroxide-ion-consuming reactions, known to proceed by nucleophilic attack of hydroxide on the ketene carbonyl group. The characteristic magnitude of these isotope effects should prove useful in identifying new examples of this reaction.

  DOI：

  10.1139/cjc-77-4-459
• 作为产物：
  描述：

  萘-1-基乙酰氯 在 benzoylquinine basic resin BEMP 作用下， 以 四氢呋喃 为溶剂， 反应 0.07h， 生成 1-萘基烯酮
  参考文献：
  名称：

  Catalytic, Asymmetric α-Halogenation

  摘要：

  DOI：

  10.1021/ja005791j

文献信息

• Scavenging of Intermediates Formed in Photolysis of α-Diazocarbonyl Compounds and Hydroxycyclopropenones. Implication on the Mechanism of the Photo-Wolff Reaction
  作者：Y. Chiang、A. J. Kresge、V. V. Popik

  DOI：10.1021/ja9906406

  日期：1999.6.1

  α-diazocarbonyl compounds was addressed by comparing pyridine scavenging of transients generated by laser flash photolysis of benzoyldiazomethane and 1-naphthoyldiazomethane with pyridine scavenging of transients formed by flash photolysis of the corresponding arylhydroxycyclopropenones. The rate laws for the scavenging process in the two different photoreactions in aqueous solution were found to be

  α-羰基卡宾中间体是否在α-重氮羰基化合物的光沃尔夫反应中作为乙烯酮前体形成的问题通过比较苯甲酰重氮甲烷和1-萘甲酰基重氮甲烷的激光闪光光解产生的瞬变的吡啶清除与由以下形成的瞬变的吡啶清除得到解决相应芳基羟基环丙烯酮的闪光光解。发现水溶液中两种不同光反应中清除过程的速率定律完全相同，并且由于乙烯酮中间体对两种反应都是共同的，而 α-羰基卡宾不是，因此瞬态被确定为乙烯酮。这些乙烯酮中间体在光沃尔夫反应中的形成发生在激光脉冲持续时间内（约 20 ns），以及 α-羰基卡宾中间体，
• US4919724A
  申请人：——

  公开号：US4919724A

  公开（公告）日：1990-04-24
• Catalytic, Asymmetric α-Halogenation
  作者：Harald Wack、Andrew E. Taggi、Ahmed M. Hafez、William J. Drury、Thomas Lectka

  DOI：10.1021/ja005791j

  日期：2001.2.1
• Solvent isotope effect on the hydroxide-ion-catalyzed hydration of ketenes in aqueous solution
  作者：J. Andraos、Y. Chiang、S.J. Eustace、A.J. Kresge、S.W. Paine、V.V. Popik、K. Sung

  DOI：10.1139/cjc-77-4-459

  日期：——

  Five ketenes, phenyl(ethyl)ketene, phenyl(methylthio)ketene, diphenylketene, pentafluorophenylketene, and 1-naphthylketene, were generated flash photolytically and solvent isotope effects (H2O vs. D2O) on their hydroxide-ion-catalyzed hydration in aqueous solution were determined. The values obtained are all weakly inverse and closely similar (k(HO)/k(DO) = 0.76-0.97), as expected for these fast, hydroxide-ion-consuming reactions, known to proceed by nucleophilic attack of hydroxide on the ketene carbonyl group. The characteristic magnitude of these isotope effects should prove useful in identifying new examples of this reaction.