3-([1-biphenyl]-4-yl)-1,3-diphenylpropan-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 3-([1-biphenyl]-4-yl)-1,3-diphenylpropan-1-one
• 英文别名: (3S)-1,3-diphenyl-3-(4-phenylphenyl)propan-1-one
• 化学式: C₂₇H₂₂O
• 分子量: 362.471
• InChiKey: ATXZIRIZVDZMSS-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-(biphenyl-4-yl)-1-phenylprop-2-en-1-one 、 苯硼酸 在 potassium phosphate 、 trans-bis(μ-chloro)bis[(S)-1-[1-(diphenylphospha)ethyl]naphthylenyl-C(2),P]dipalladium(II) 、 三苯基膦 作用下， 以 甲苯 为溶剂， 生成 3-([1-biphenyl]-4-yl)-1,3-diphenylpropan-1-one 、 3-([1-biphenyl]-4-yl)-1,3-diphenylpropan-1-one
  参考文献：
  名称：

  Palladacycles作为非铑的替代品，用于芳基硼酸向α，β-不饱和烯酮的不对称共轭1,4-加成反应的评估

  摘要：

  AbstractThe asymmetric conjugate 1,4‐addition of arylboronic acids to α,β‐unsaturated carbonyl compounds is an extremely versatile and widely used organic transformation. While the rhodium(I)‐catalysed reaction has been thoroughly explored, the asymmetric palladium‐catalysed protocol is far less developed and understood, particularly with acyclic enones as substrates. Herein, we report the systematic evaluation of a series of metallacycles for this reaction and the conjugate addition of arylboronic acids to a wide range of α,β‐unsaturated enones, catalysed by an easily accessible and robust chiral phosphapalladacycle in high yields and enantioselectivities.magnified image

  DOI：

  10.1002/adsc.201400473

文献信息

• Evaluation of Palladacycles as a Non-Rhodium Based Alternative for the Asymmetric Conjugate 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Enones
  作者：Jonathan Wong、Kennard Gan、Houguang Jeremy Chen、Sumod A. Pullarkat

  DOI：10.1002/adsc.201400473

  日期：2014.11.3

  AbstractThe asymmetric conjugate 1,4‐addition of arylboronic acids to α,β‐unsaturated carbonyl compounds is an extremely versatile and widely used organic transformation. While the rhodium(I)‐catalysed reaction has been thoroughly explored, the asymmetric palladium‐catalysed protocol is far less developed and understood, particularly with acyclic enones as substrates. Herein, we report the systematic evaluation of a series of metallacycles for this reaction and the conjugate addition of arylboronic acids to a wide range of α,β‐unsaturated enones, catalysed by an easily accessible and robust chiral phosphapalladacycle in high yields and enantioselectivities.magnified image