(Z)-7-bromo-4'-fluoro-5-heptenophenone | 217454-46-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-7-bromo-4'-fluoro-5-heptenophenone
• 英文别名: (Z)-7-bromo-1-(4-fluorophenyl)hept-5-en-1-one
• CAS: 217454-46-1
• 化学式: C₁₃H₁₄BrFO
• 分子量: 285.156
• InChiKey: NNPXMPVBSOKKPV-RQOWECAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-7-bromo-4'-fluoro-5-heptenophenone 在 indium 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 以87%的产率得到
  参考文献：
  名称：

  Paquette, Leo A., Synthesis, 2003, # 5, p. 765 - 774

  摘要：

  DOI：
• 作为产物：
  描述：

  (4-cyanobutyl)triphenylphosphonium bromide 在 盐酸 、 溴 、 双(三甲基硅烷基)氨基钾 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 6.25h， 生成 (Z)-7-bromo-4'-fluoro-5-heptenophenone
  参考文献：
  名称：

  Intramolecular Cyclization of Tethered Phenyl Ketones. Complementary Stereochemical Results Arising from the Indium-Promoted Ring Closure of Allyl Bromides and the Fluoride Ion-Induced Desilylation of Allylsilanes

  摘要：

  dThe intramolecular indium-promoted cyclization of 4'-substituted (Z)- and (E)-7-bromo-5-heptenophenones has been examined in aqueous tetrahydrofuran. In every instance, ring closure occurred to deliver the syn-2-vinylcyclopentanol exclusively. The corresponding allylsilanes have been prepared as well, and the course of their fluoride ion-induced cyclization was also studied. In these systems, a kinetic bias for formation of the anti-2-vinylcyclopentanol is observed, although not with the same exclusivity. Accordingly, complementarity in product diastereoselectivity can be realized in purposeful fashion. The data acquired in this investigation suggest that the indium-catalyzed reactions involve intramolecularly coordinated transition states where development of a cis 5/6-bicyclic framework is most energetically feasible. In contrast, the silanes appear to utilize open-chain antiperiplanar transition states. While the latter are not particularly sensitive to double-bond geometry, they are responsive to steric compression involving the aryl group.

  DOI：

  10.1021/jo981683s

文献信息

• Paquette, Leo A., Synthesis, 2003, # 5, p. 765 - 774
  作者：Paquette, Leo A.

  DOI：——

  日期：——
• Intramolecular Cyclization of Tethered Phenyl Ketones. Complementary Stereochemical Results Arising from the Indium-Promoted Ring Closure of Allyl Bromides and the Fluoride Ion-Induced Desilylation of Allylsilanes
  作者：Leo A. Paquette、José L. Mendez-Andino

  DOI：10.1021/jo981683s

  日期：1998.11.1

  dThe intramolecular indium-promoted cyclization of 4'-substituted (Z)- and (E)-7-bromo-5-heptenophenones has been examined in aqueous tetrahydrofuran. In every instance, ring closure occurred to deliver the syn-2-vinylcyclopentanol exclusively. The corresponding allylsilanes have been prepared as well, and the course of their fluoride ion-induced cyclization was also studied. In these systems, a kinetic bias for formation of the anti-2-vinylcyclopentanol is observed, although not with the same exclusivity. Accordingly, complementarity in product diastereoselectivity can be realized in purposeful fashion. The data acquired in this investigation suggest that the indium-catalyzed reactions involve intramolecularly coordinated transition states where development of a cis 5/6-bicyclic framework is most energetically feasible. In contrast, the silanes appear to utilize open-chain antiperiplanar transition states. While the latter are not particularly sensitive to double-bond geometry, they are responsive to steric compression involving the aryl group.