1-(pentafluorophenyl)-1-phenyl-2-propanone | 132317-37-4

• 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-(pentafluorophenyl)-1-phenyl-2-propanone
• CAS: 132317-37-4
• 化学式: C₁₅H₉F₅O
• 分子量: 300.228
• InChiKey: LIUPGRSUWOLFJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(pentafluorophenyl)-1-phenyl-2-propanone 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 三苯基膦 sodium hydroxide 、 双氧水 、 四氯化钛 、 锌 、 儿萘酚硼烷 作用下， 反应 14.5h， 生成 anti-2-methyl-3-(pentafluorophenyl)-3-phenyl-1-propanol
  参考文献：
  名称：

  Substrate-controlled diastereoselectivities in catalyzed and uncatalyzed hydroborations of acyclic allylic alcohol derivatives: secondary orbital effects involving d.pi.-p.pi. interactions

  摘要：

  Rhodium-mediated hydroborations of allylic alcohol derivatives 1-9 followed by oxidation give predominantly syn-2-methyl 1,3-diols whereas conventional hydroborations of the same substrates afford mostly anti products. It is proposed that mixing of delta*-orbitals involved in bonding at the asymmetric center with pi*-orbitals of the alkene lowers the LUMO involved in complexation of rhodium, and this could control diastereofacial selectivities in catalyzed hydroborations. Steric effects in catalyzed hydroborations are also discussed. The resulting hypotheses are tested with respect to catalyzed and uncatalyzed hydroborations of phenyl-substituted allylic alcohol derivatives 17-19 and Ph(C6F5)CHCM(e) = CH2 (21) (a model substrate with aromatic groups of a similar size but different electronic properties attached to the chiral center). All experimental observations described here for catalyzed hydroborations of chiral alkenes are consistent with the proposals outlined above.

  DOI：

  10.1021/jo00003a023
• 作为产物：
  描述：

  溴五氟苯 在 iron(III) chloride 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 0.33h， 生成 1-(pentafluorophenyl)-1-phenyl-2-propanone
  参考文献：
  名称：

  使用两性溴全氟芳烃对酮进行一锅芳基环氧化

  摘要：

  报道了通过烯醇化酮1与溴五氟苯 (PFP​​Br) 和衍生物 ( 3 )的芳基化环氧化反应合成全氟芳基环氧乙烷2的一锅法。在这种高效、易于放大、非对映选择性环氧化反应中，PFPBr 被用作 Br +和 PFP -的等价物，该反应可生产合成有用的多氟芳基环氧乙烷。

  DOI：

  10.1002/anie.201106969

文献信息

• One-Pot Arylative Epoxidation of Ketones by Employing Amphoteric Bromoperfluoroarenes
  作者：Zhou Li、Vladimir Gevorgyan

  DOI：10.1002/anie.201106969

  日期：2012.1.27

  A one‐pot cascade synthesis of perfluoroaryl oxiranes 2 by the arylative epoxidation of enolizable ketones 1 with bromopentafluorobenzene (PFPBr) and derivatives (3) is reported. PFPBr is utilized as an equivalent of Br+ and PFP− in this highly efficient, easily scaled‐up, diastereoselective epoxidation reaction, which produces synthetically useful polyfluoroaryl oxiranes.

  报道了通过烯醇化酮1与溴五氟苯 (PFP​​Br) 和衍生物 ( 3 )的芳基化环氧化反应合成全氟芳基环氧乙烷2的一锅法。在这种高效、易于放大、非对映选择性环氧化反应中，PFPBr 被用作 Br +和 PFP -的等价物，该反应可生产合成有用的多氟芳基环氧乙烷。
• Substrate-controlled diastereoselectivities in catalyzed and uncatalyzed hydroborations of acyclic allylic alcohol derivatives: secondary orbital effects involving d.pi.-p.pi. interactions
  作者：Kevin Burgess、Juanita Cassidy、Michael J. Ohlmeyer

  DOI：10.1021/jo00003a023

  日期：1991.2

  Rhodium-mediated hydroborations of allylic alcohol derivatives 1-9 followed by oxidation give predominantly syn-2-methyl 1,3-diols whereas conventional hydroborations of the same substrates afford mostly anti products. It is proposed that mixing of delta*-orbitals involved in bonding at the asymmetric center with pi*-orbitals of the alkene lowers the LUMO involved in complexation of rhodium, and this could control diastereofacial selectivities in catalyzed hydroborations. Steric effects in catalyzed hydroborations are also discussed. The resulting hypotheses are tested with respect to catalyzed and uncatalyzed hydroborations of phenyl-substituted allylic alcohol derivatives 17-19 and Ph(C6F5)CHCM(e) = CH2 (21) (a model substrate with aromatic groups of a similar size but different electronic properties attached to the chiral center). All experimental observations described here for catalyzed hydroborations of chiral alkenes are consistent with the proposals outlined above.