9-(9H-fluoren-9-ylidene)-2,7-dichloro-9H-fluorene | 56485-97-3

• 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-dichloro-9H-fluorene
• 英文别名: 2,7-Dichlor-9,9'-bifluorenyliden；2,7-Dichloro-9-fluoren-9-ylidenefluorene
• CAS: 56485-97-3
• 化学式: C₂₆H₁₄Cl₂
• 分子量: 397.303
• InChiKey: LNTKTBCFAHEFMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 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-dichloro-9H-fluorene 在 五氟化锑 作用下， 以 氯氟磺酰 为溶剂， 生成 2,7-dichloro-9-fluoren-9-ylium-9-ylfluoren-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：

  2,7-二氯芴 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 生成 9-(9H-fluoren-9-ylidene)-2,7-dichloro-9H-fluorene
  参考文献：
  名称：

  氯代 9,9'-二芴基与芴的迈克尔反应及与类似卤素化合物的比较

  摘要：

  研究了 2-氯-和 2,7-二氯-9,9'-二芴基与芴的迈克尔反应。这些产物的结构通过 9-锂硫芴和 9-溴-9,9'-二芴基的成熟反应通过合成确认。一些异常化合物的形成可以通过 9,9'-二芴基与 2,7-二氯芴与溴代衍生物的反应中间形成 2,7-二氯-9,9'-二芴基来解释。相应的氟和碘系列主要产生正常的加成产物。这些差异是根据卤素取代基的感应和空间效应来解释的。

  DOI：

  10.1246/bcsj.48.586

文献信息

• 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.
• 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：——
• The Michael Reactions of Chloro-substituted-9,9′-bifluorenylidenes with Fluorenes and a Comparison with Analogous Halogen Compounds
  作者：Masahiro Minabe、Kazuo Suzuki

  DOI：10.1246/bcsj.48.586

  日期：1975.2

  The Michael reactions of 2-chloro- and 2,7-dichloro-9,9′-bifluorenylidenes with fluorenes were investigated. Structures of these products were confirmed by syntheses through the well-established reactions of 9-lithiofluorenes and 9-bromo-9,9′-bifluorenyls. The formation of some abnormal compounds is explained by intermediary formation of 2,7-dichloro-9,9′-bifluorenylidene from the reaction of 9,9′-bifluorenylidene

  研究了 2-氯-和 2,7-二氯-9,9'-二芴基与芴的迈克尔反应。这些产物的结构通过 9-锂硫芴和 9-溴-9,9'-二芴基的成熟反应通过合成确认。一些异常化合物的形成可以通过 9,9'-二芴基与 2,7-二氯芴与溴代衍生物的反应中间形成 2,7-二氯-9,9'-二芴基来解释。相应的氟和碘系列主要产生正常的加成产物。这些差异是根据卤素取代基的感应和空间效应来解释的。