1-溴-4-苯基二环[2.2.2]辛烷 | 714-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-溴-4-苯基二环[2.2.2]辛烷
• 英文名称: 1-bromo-4-phenylbicyclo<2.2.2>octane
• 英文别名: 1-bromo-4-phenylbicyclo[2.2.2]octane；1-Brom-4-phenyl-bicyclo <2.2.2> octan；4-Phenyl-1-brom-bicyclo <2.2.2> octan；1-Brom-4-phenyl-bicyclo<2.2.2>octan；Bicyclo[2.2.2]octane, 1-bromo-4-phenyl-
• CAS: 714-68-1
• 化学式: C₁₄H₁₇Br
• 分子量: 265.193
• InChiKey: GVABUODCBHIMKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  1-溴-4-苯基二环[2.2.2]辛烷 在 吡啶 、 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 4-苯基双环[2.2.2]辛烷-1-羧酸
  参考文献：
  名称：

  The Preparation of 1-Carboxy-4-substituted Bicyclo[2.2.2]octanes

  摘要：

  DOI：

  10.1021/ja01077a030
• 作为产物：
  描述：

  1-苯基双环[2.2.2]辛烷-4-醇 在 磷酸 、 potassium bromide 作用下， 反应 1.0h， 以70%的产率得到1-溴-4-苯基二环[2.2.2]辛烷
  参考文献：
  名称：

  Kopecky, Jan; Smejkal, Jaroslav, Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 11, p. 2965 - 2970

  摘要：

  DOI：

文献信息

• Preparation of 4-substituted 1-methoxycarbonylbicyclo[2.2.2]octanes, 4-substituted 1-phenylbicyclo[2.2.2]octanes, 4-substituted 1-p-nitrophenylbicyclo[2.2.2]octanes and 1,4-disubstituted bicyclo[2.2.2]octanes
  作者：Norman Bellamy Chapman、S. Sotheeswaran、K. J. Toyne

  DOI：10.1021/jo00829a010

  日期：1970.4
• 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.
• 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：——
• KOPECKY J.; SMEJKAL J., COLLECT. CZECH. CHEM. COMMUN., 1980, 45, NO 11, 2965-2970
  作者：KOPECKY J.、 SMEJKAL J.

  DOI：——

  日期：——
• Kopecky, Jan; Smejkal, Jaroslav, Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 11, p. 2965 - 2970
  作者：Kopecky, Jan、Smejkal, Jaroslav

  DOI：——

  日期：——

表征谱图