9-(9H-fluoren-9-ylidene)-2,7-difluoro-9H-fluorene | 33294-99-4

• 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-difluoro-9H-fluorene
• 英文别名: 2,7-Difluoro-9,9'-bifluorenyliden；9-Fluoren-9-ylidene-2,7-difluorofluorene
• CAS: 33294-99-4
• 化学式: C₂₆H₁₄F₂
• 分子量: 364.394
• InChiKey: JOZQTLOAJXIIMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 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：
  2

反应信息

• 作为反应物：
  描述：

  9-(9H-fluoren-9-ylidene)-2,7-difluoro-9H-fluorene 在 盐酸 、 锌 作用下， 以 溶剂黄146 为溶剂， 生成 2,7-Difluoro-9,9'-bifluorenyl
  参考文献：
  名称：

  氟代-9,9'-二芴基和-芴的迈克尔反应及相关化合物的合成

  摘要：

  进行了氟取代的9,9'-二芴基与芴的迈克尔反应；得到了正常的加成产物，氟取代的亚联苯丙烷，但没有分离出异常产物。合成了一些新的氟取代芴、-9,9'-联芴、-9,9'-联芴和-α,δ-二联亚苯基丁二烯。氟取代的亚联苯丙烷的结构通过 9-锂硫芴和 9-溴-9,9'-二芴基的锂-卤素互变反应得到证实。氟取代的亚联苯丙烷的热解得到氟取代或非氟取代的-9,9'-二芴基、-9,9'-二芴基、-芴和-芴酮。差示扫描量热法应用于氟取代的 9,9'-二芴基和三联苯丙烷。

  DOI：

  10.1246/bcsj.44.1614
• 作为产物：
  描述：

  2,7-二氨基-9-芴酮 在 吡啶 、 正丁基锂 、 氢氟酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.12h， 生成 9-(9H-fluoren-9-ylidene)-2,7-difluoro-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.
• The Michael Reaction of Fluoro-substituted-9,9′-Bifluorenylidenes and -Fluorenes, and the Syntheses of Some Related Compounds
  作者：Masahiro Minabe、Akio Tanaka、Masahiro Wakui、Kazuo Suzuki

  DOI：10.1246/bcsj.44.1614

  日期：1971.6

  The Michael reaction of fluoro-substituted 9,9′-bifluorenylidenes and fluorenes was carried out; the normal addition products, fluoro-substituted tribiphenylenepropanes, were obtained, but no abnormal product was isolated. Some new fluoro-substituted-fluorenes, -9,9′-bifluorenylidenes, -9,9′-bifluorenyls and -α,δ-dibiphenylenebutadienes, were synthesized. The structures of the fluoro-substituted t

  进行了氟取代的9,9'-二芴基与芴的迈克尔反应；得到了正常的加成产物，氟取代的亚联苯丙烷，但没有分离出异常产物。合成了一些新的氟取代芴、-9,9'-联芴、-9,9'-联芴和-α,δ-二联亚苯基丁二烯。氟取代的亚联苯丙烷的结构通过 9-锂硫芴和 9-溴-9,9'-二芴基的锂-卤素互变反应得到证实。氟取代的亚联苯丙烷的热解得到氟取代或非氟取代的-9,9'-二芴基、-9,9'-二芴基、-芴和-芴酮。差示扫描量热法应用于氟取代的 9,9'-二芴基和三联苯丙烷。