1-(9-Hydroxy-9H-fluoren-9-yl)-2-methyl-propan-1-one | 288845-61-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 1-(9-Hydroxy-9H-fluoren-9-yl)-2-methyl-propan-1-one
• 英文别名: 1-(9-Hydroxyfluoren-9-yl)-2-methylpropan-1-one
• CAS: 288845-61-4
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: QCXPRNOUCHOGMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(9-Hydroxy-9H-fluoren-9-yl)-2-methyl-propan-1-one 在 氯化亚砜 、 sodium carbonate 作用下， 以 吡啶 、 乙醚 为溶剂， 反应 84.0h， 生成 (E)-1-(9-chlorofluoren-9-yl)-N-methoxy-2-methylpropan-1-imine
  参考文献：
  名称：

  Effect of oxime substituents on 9-fluorenyl carbocations

  摘要：

  9-Fluorenyl carbocations substituted with the oxime functional groups CH=NOCH3, CH3C=NOCH3, and i-PrC=NOCH3 were generated by solvolyses of the corresponding chlorides in methanol, These cations form at rates which greatly exceed those of formation of the parent 9-fluorenyl cation. Relative rate data suggest that stabilization of 9-fluorenyl cations by CH=NOCH3 is greater than stabilization by CH3C=NOCH3, which is in turn greater than that by i-PrC=NOCH3. Computational studies on these cations show that the oxime group is progressively rotated out of conjugation with the cationic center as the oxime group becomes larger. These rate and computational studies also suggest that 9-fluorenyl cations are not antiaromatic. They are essentially delocalized 'nonatetraenyl' cations, where formally antiaromatic resonance forms contribute little to the overall structure. Copyright (C) 2000 John Wiley & Sons, Ltd.

  DOI：

  10.1002/1099-1395(200006)13:6<337::aid-poc249>3.0.co;2-t
• 作为产物：
  描述：

  9-cyano-9-(trimethylsilyloxy)-fluorene 、 异丙基溴化镁 在 硫酸 、 水 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 反应 24.0h， 以55%的产率得到1-(9-Hydroxy-9H-fluoren-9-yl)-2-methyl-propan-1-one
  参考文献：
  名称：

  Effect of oxime substituents on 9-fluorenyl carbocations

  摘要：

  9-Fluorenyl carbocations substituted with the oxime functional groups CH=NOCH3, CH3C=NOCH3, and i-PrC=NOCH3 were generated by solvolyses of the corresponding chlorides in methanol, These cations form at rates which greatly exceed those of formation of the parent 9-fluorenyl cation. Relative rate data suggest that stabilization of 9-fluorenyl cations by CH=NOCH3 is greater than stabilization by CH3C=NOCH3, which is in turn greater than that by i-PrC=NOCH3. Computational studies on these cations show that the oxime group is progressively rotated out of conjugation with the cationic center as the oxime group becomes larger. These rate and computational studies also suggest that 9-fluorenyl cations are not antiaromatic. They are essentially delocalized 'nonatetraenyl' cations, where formally antiaromatic resonance forms contribute little to the overall structure. Copyright (C) 2000 John Wiley & Sons, Ltd.

  DOI：

  10.1002/1099-1395(200006)13:6<337::aid-poc249>3.0.co;2-t

文献信息

• Effect of oxime substituents on 9-fluorenyl carbocations
  作者：Xavier Creary、Allison Wolf

  DOI：10.1002/1099-1395(200006)13:6<337::aid-poc249>3.0.co;2-t

  日期：2000.6

  9-Fluorenyl carbocations substituted with the oxime functional groups CH=NOCH3, CH3C=NOCH3, and i-PrC=NOCH3 were generated by solvolyses of the corresponding chlorides in methanol, These cations form at rates which greatly exceed those of formation of the parent 9-fluorenyl cation. Relative rate data suggest that stabilization of 9-fluorenyl cations by CH=NOCH3 is greater than stabilization by CH3C=NOCH3, which is in turn greater than that by i-PrC=NOCH3. Computational studies on these cations show that the oxime group is progressively rotated out of conjugation with the cationic center as the oxime group becomes larger. These rate and computational studies also suggest that 9-fluorenyl cations are not antiaromatic. They are essentially delocalized 'nonatetraenyl' cations, where formally antiaromatic resonance forms contribute little to the overall structure. Copyright (C) 2000 John Wiley & Sons, Ltd.