9-Brom-9,9'-bifluorenyl | 13295-92-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-Brom-9,9'-bifluorenyl
• 英文别名: 9-bromo-9,9'-bifluorene；9-bromo-[9,9']bifluorenyl；9-Brom-[9,9']bifluorenyl；9-Brom-dibiphenylenethan；9-Brom-9,9'-bifluoranyl；9-bromo-9-(9H-fluoren-9-yl)fluorene
• CAS: 13295-92-6
• 化学式: C₂₆H₁₇Br
• 分子量: 409.325
• InChiKey: LWTNDCPNKPFEIT-UHFFFAOYSA-N

物化性质

• 熔点：
  166 °C
• 沸点：
  480.9±45.0 °C(Predicted)
• 密度：
  1.445±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 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-Brom-9,9'-bifluorenyl 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 特戊醛
  参考文献：
  名称：

  Carey, Edwin; O'Ferrall, Rory A. More; Vernon, Nicholas M., Journal of the Chemical Society. Perkin transactions II, 1982, p. 1581 - 1586

  摘要：

  DOI：
• 作为产物：
  描述：

  9-hydroxy-9-fluorenylfluorene 在 氢溴酸 作用下， 以 乙醚 为溶剂， 生成 9-Brom-9,9'-bifluorenyl
  参考文献：
  名称：

  Carey, Edwin; O'Ferrall, Rory A. More; Vernon, Nicholas M., Journal of the Chemical Society. Perkin transactions II, 1982, p. 1581 - 1586

  摘要：

  DOI：

文献信息

• 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。
• Formation of 9,9′:9′,9″-Terfluorenyl Isomers Using Metalated Fluorenes as Synthetic Intermediates
  作者：Masahiro Minabe、Kazuo Suzuki

  DOI：10.1246/bcsj.48.1301

  日期：1975.4

  Rotational isomers of 9,9′: 9′,9″-terfluorenyl were obtained by the addition of 9-lithiofluorene to 9,9′-bifluorenylidene (III). 2,7-Dibromo- (VI) and 2,7,2″,7″-tetrabromo-9′,9″-terfluorenyl (VIII) resulted from similar reactions of the corresponding bromo-derivatives. 9-Lithio-9,9′-bifluorenyl was treated with 9-bromo-9,9′-bifluorenyl to give 9,9′-bis(9,9′-bifluorenyl) (X), 9,9′: 9′,9″-terfluorenyl

  通过将 9-锂硫芴加成到 9,9'-二芴基 (III) 获得 9,9': 9',9"-三芴基的旋转异构体。2,7-Dibromo-(VI) 和 2,7,2",7"-tetrabromo-9',9"-terfluorenyl (VIII) 由相应溴代衍生物的类似反应产生。9-Lithio-9,9'-bifluorenyl 用 9-bromo-9,9'-bifluorenyl 处理得到 9,9'-bis(9,9'-bifluorenyl) (X), 9,9': 9' ,9"-三芴基异构体（mp 293 °C (dec) (I) 和 mp 257 °C (dec) (II)）、9,9'-二芴基 (IX)、III 和芴酮。I 被金属钾异构化得到另一个旋转异构体 II，它分解成其组分 IX、III 和芴 (IV)。
• 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。
• 1,9-CYCLOHEXYLENEFLUORENE, A PENTACYCLIC RING SYSTEM
  作者：CHARLES D. HURD、JAMES D. MOLD

  DOI：10.1021/jo01161a003

  日期：1948.5
• 9-Fluorenyl 9-(p-tolylsulfonyl)-9-fluorenyl disulfide: the unexpected product of the reaction of 9-bromofluorene and potassium p-toluenethiosulfonate and the mechanism of its formation
  作者：John L. Kice、Tatianna G. Kutateladze、Lidia Kupczyk-Subotkowska

  DOI：10.1021/jo00021a036

  日期：1991.10

  Reaction of potassium p-toluenethiosulfonate with 9-bromofluorene leads, not to the expected 9-fluorenyl p-toluenethiosulfonate (3), but rather to a product shown to be 9-fluorenyl 9-(p-tolylsulfonyl)-9-fluorenyl disulfide (7, R = 9-fluorenyl) (eq 11). This disulfide of unusual structure is shown to arise as a result of the following reaction sequence: (a) initial formation of 3; (b) a facile elimination of 3 (due to the acidity of the 9-H), forming p-toluenesulfinic acid and 9-thiofluorenone (4); (c) addition of p-CH3C6HSO2- to 4 to give alpha-sulfonyl thiolate ion 16; and (d) reaction of 16 with remaining 3 (in a rapid displacement at the dicoordinate sulfur) to give 7 plus regeneration of p-CH3C6H4SO2-.