| 132317-41-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• CAS: 132317-41-0
• 化学式: C₁₆H₁₂F₄O
• 分子量: 296.264
• InChiKey: OHXUKJDPSRMTJJ-PSASIEDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  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 、 sodium hydride 、 锌 、 儿萘酚硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 25.5h， 生成
  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