9-(9H-fluoren-9-ylidene)-2,7-dimethyl-9H-fluorene | 205446-02-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-(9H-fluoren-9-ylidene)-2,7-dimethyl-9H-fluorene
• 英文别名: 9-Fluoren-9-ylidene-2,7-dimethylfluorene
• CAS: 205446-02-2
• 化学式: C₂₈H₂₀
• 分子量: 356.467
• InChiKey: AUCOSVXAXNUOLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  9-(9H-fluoren-9-ylidene)-2,7-dimethyl-9H-fluorene 在 五氟化锑 作用下， 以 氯氟磺酰 为溶剂， 生成 9-Fluoren-9-ylium-9-yl-2,7-dimethylfluoren-9-ylium
  参考文献：
  名称：

  Dications of Fluorenylidenes. Electronic Effects on the Paratropicity/Antiaromaticity of 2,7-Disubstituted Fluorenyl Cations

  摘要：

  Oxidation of 2,7-disubstituted tetrabenzo[5.5]fulvalene derivatives 1a-d resulted in the formation of dications which are fluorenyl cations linked by a single bond. These fluorenyl cations exhibit significant paratropicity in the H-1 NMR spectrum, which is attributed to an antiaromatic ring current. Interaction of the perpendicular ring systems is evident in the upfield shift of carbons a and a', presumably due to sigma-p donation. The lack of variation in the upfield shift of carbons a and a', compared to previously reported systems, is attributed to the similarities of the geometries of 1a-d(2+). Substitution at a remote site affects the antiaromaticity of the unsubstituted fluorenyl cation, but the nature of the effect of the substituent is not understood. Direct substitution on the fluorenyl cation by substituents which increase electron density, either through inductive It polarization or through resonance, cause a paratropic shift in the probe proton.

  DOI：

  10.1021/jo972202s
• 作为产物：
  描述：

  2,7-Dimethyl-9'H-[9,9']bifluorenyl-9-ol 在 硫酸 、 乙酸酐 作用下， 以67.7%的产率得到9-(9H-fluoren-9-ylidene)-2,7-dimethyl-9H-fluorene
  参考文献：
  名称：

  Dications of Fluorenylidenes. Electronic Effects on the Paratropicity/Antiaromaticity of 2,7-Disubstituted Fluorenyl Cations

  摘要：

  Oxidation of 2,7-disubstituted tetrabenzo[5.5]fulvalene derivatives 1a-d resulted in the formation of dications which are fluorenyl cations linked by a single bond. These fluorenyl cations exhibit significant paratropicity in the H-1 NMR spectrum, which is attributed to an antiaromatic ring current. Interaction of the perpendicular ring systems is evident in the upfield shift of carbons a and a', presumably due to sigma-p donation. The lack of variation in the upfield shift of carbons a and a', compared to previously reported systems, is attributed to the similarities of the geometries of 1a-d(2+). Substitution at a remote site affects the antiaromaticity of the unsubstituted fluorenyl cation, but the nature of the effect of the substituent is not understood. Direct substitution on the fluorenyl cation by substituents which increase electron density, either through inductive It polarization or through resonance, cause a paratropic shift in the probe proton.

  DOI：

  10.1021/jo972202s

文献信息

• Levy, Amalia; Rakowitz, Amber; Mills, Nancy S., Journal of Organic Chemistry, 2003, vol. 68, # 10, p. 3990 - 3998
  作者：Levy, Amalia、Rakowitz, Amber、Mills, Nancy S.

  DOI：——

  日期：——
• Dications of Fluorenylidenes. Electronic Effects on the Paratropicity/Antiaromaticity of 2,7-Disubstituted Fluorenyl Cations
  作者：Nancy S. Mills、Ellen E. Burns、Jonathan Hodges、Jennifer Gibbs、Edward Esparza、James L. Malandra、Josh Koch

  DOI：10.1021/jo972202s

  日期：1998.5.1

  Oxidation of 2,7-disubstituted tetrabenzo[5.5]fulvalene derivatives 1a-d resulted in the formation of dications which are fluorenyl cations linked by a single bond. These fluorenyl cations exhibit significant paratropicity in the H-1 NMR spectrum, which is attributed to an antiaromatic ring current. Interaction of the perpendicular ring systems is evident in the upfield shift of carbons a and a', presumably due to sigma-p donation. The lack of variation in the upfield shift of carbons a and a', compared to previously reported systems, is attributed to the similarities of the geometries of 1a-d(2+). Substitution at a remote site affects the antiaromaticity of the unsubstituted fluorenyl cation, but the nature of the effect of the substituent is not understood. Direct substitution on the fluorenyl cation by substituents which increase electron density, either through inductive It polarization or through resonance, cause a paratropic shift in the probe proton.