1-(p-fluorophenyl)-4-phenylbicyclo<2.2.2>octane | 68756-32-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(p-fluorophenyl)-4-phenylbicyclo<2.2.2>octane
• 英文别名: 1-para-fluorophenyl-4-phenylbicyclo[2.2.2]octane；1-(4-Fluorophenyl)-4-phenylbicyclo[2.2.2]octane
• CAS: 68756-32-1
• 化学式: C₂₀H₂₁F
• 分子量: 280.385
• InChiKey: BAYPKWREOIKPGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(p-fluorophenyl)-4-phenylbicyclo<2.2.2>octane 生成 1-(p-fluorophenyl)-4-(p-nitrophenyl)bicyclo<2.2.2>octane
  参考文献：
  名称：

  Transmission of polar substituent effects in the adamantane ring system as monitored by 19F NMR: hyperconjugation as a stereoinductive factor

  摘要：

  A limited series of (E)- and (Z)-5-substituted adamant-2-yl fluorides 8 and 9, respectively, has been synthesized and characterized, and the F-19 chemical shifts have been measured in several solvents. A wide range of F-19 substituent chemical shifts (SCS, ppm) are obtained for the former system (ca. 9.1 (c-C6H12), 9.6 (CDCl3), and 11.8 (HFIP)) compared to the latter (ca. 0.6 (c-C6H12), 0.7 (CDCl3), and 2.3 (HFIP)). Factorization of the F-19 SCS into polar field (rho-F-sigma-F) and residual contributions (F-19 SCS - rho-F-sigma-F) reveals the predominance of the latter solvent-independent component for the E fluorides (8). Comparison of 8 with a similar dissection of the F-19 SCS of 4-substituted bicyclo[2.2.2]oct-1-yl fluorides 2 strongly suggests that the origin of the large residual contributions for 8 is "through-three-bond" electron delocalization or double hyperconjugation. The importance of this long-range electronic mechanism as a factor governing pi-facial diastereoselection in 2,5-disubstituted adamantanes (1) is discussed. In particular, the assertion that the p-anilino substituent is an electron donor group at remote probe or reaction sites in saturated systems is addressed.

  DOI：

  10.1021/jo00010a012
• 作为产物：
  描述：

  氟苯 、 1-溴-4-苯基二环[2.2.2]辛烷 在 三氯化铝 作用下， 反应 3.0h， 以56%的产率得到1-(p-fluorophenyl)-4-phenylbicyclo<2.2.2>octane
  参考文献：
  名称：

  Transmission of polar substituent effects in the adamantane ring system as monitored by 19F NMR: hyperconjugation as a stereoinductive factor

  摘要：

  A limited series of (E)- and (Z)-5-substituted adamant-2-yl fluorides 8 and 9, respectively, has been synthesized and characterized, and the F-19 chemical shifts have been measured in several solvents. A wide range of F-19 substituent chemical shifts (SCS, ppm) are obtained for the former system (ca. 9.1 (c-C6H12), 9.6 (CDCl3), and 11.8 (HFIP)) compared to the latter (ca. 0.6 (c-C6H12), 0.7 (CDCl3), and 2.3 (HFIP)). Factorization of the F-19 SCS into polar field (rho-F-sigma-F) and residual contributions (F-19 SCS - rho-F-sigma-F) reveals the predominance of the latter solvent-independent component for the E fluorides (8). Comparison of 8 with a similar dissection of the F-19 SCS of 4-substituted bicyclo[2.2.2]oct-1-yl fluorides 2 strongly suggests that the origin of the large residual contributions for 8 is "through-three-bond" electron delocalization or double hyperconjugation. The importance of this long-range electronic mechanism as a factor governing pi-facial diastereoselection in 2,5-disubstituted adamantanes (1) is discussed. In particular, the assertion that the p-anilino substituent is an electron donor group at remote probe or reaction sites in saturated systems is addressed.

  DOI：

  10.1021/jo00010a012

文献信息

• METAL COMPLEXES FOR USE AS EMITTERS IN ORGANIC ELECTROLUMINESCENCE DEVICES
  申请人：Merck Patent GmbH

  公开号：US20190161510A1

  公开（公告）日：2019-05-30

  The present invention relates to metal complexes and electronic devices, in particular organic electroluminescent devices containing said metal complexes.

  本发明涉及金属配合物和电子设备，特别是含有所述金属配合物的有机电致发光器件。
• Adcock, William; Aldous, Graham L., Journal of Organometallic Chemistry, 1980, vol. 201, p. 411 - 432
  作者：Adcock, William、Aldous, Graham L.

  DOI：——

  日期：——
• [DE] METALLKOMPLEXE FÜR DEN EINSATZ ALS EMITTER IN ORGANISCHEN ELEKTROLUMINESZENZVORRICHTUNGEN<br/>[EN] METAL COMPLEXES FOR USE AS EMITTERS IN ORGANIC ELECTROLUMINESCENCE DEVICES<br/>[FR] COMPLEXES MÉTALLIQUES TROUVANT APPLICATION COMME ÉMETTEURS DANS DES DISPOSITIFS ÉLECTROLUMINESCENTS ORGANIQUES
  申请人：MERCK PATENT GMBH

  公开号：WO2018019688A1

  公开（公告）日：2018-02-01

  Die vorliegende Erfindung betrifft Metallkomplexe sowie elektronische Vorrichtungen, insbesondere organische Elektrolumineszenzvorrichtungen, enthaltend diese Metallkomplexe.
• Transmission of polar substituent effects in the adamantane ring system as monitored by 19F NMR: hyperconjugation as a stereoinductive factor
  作者：William Adcock、Neil A. Trout

  DOI：10.1021/jo00010a012

  日期：1991.5

  A limited series of (E)- and (Z)-5-substituted adamant-2-yl fluorides 8 and 9, respectively, has been synthesized and characterized, and the F-19 chemical shifts have been measured in several solvents. A wide range of F-19 substituent chemical shifts (SCS, ppm) are obtained for the former system (ca. 9.1 (c-C6H12), 9.6 (CDCl3), and 11.8 (HFIP)) compared to the latter (ca. 0.6 (c-C6H12), 0.7 (CDCl3), and 2.3 (HFIP)). Factorization of the F-19 SCS into polar field (rho-F-sigma-F) and residual contributions (F-19 SCS - rho-F-sigma-F) reveals the predominance of the latter solvent-independent component for the E fluorides (8). Comparison of 8 with a similar dissection of the F-19 SCS of 4-substituted bicyclo[2.2.2]oct-1-yl fluorides 2 strongly suggests that the origin of the large residual contributions for 8 is "through-three-bond" electron delocalization or double hyperconjugation. The importance of this long-range electronic mechanism as a factor governing pi-facial diastereoselection in 2,5-disubstituted adamantanes (1) is discussed. In particular, the assertion that the p-anilino substituent is an electron donor group at remote probe or reaction sites in saturated systems is addressed.