(+)-3-(naphthalen-2-yl)-1,3-diphenylpropan-1-one | 1383843-83-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (+)-3-(naphthalen-2-yl)-1,3-diphenylpropan-1-one
• 英文别名: (S)-3-(naphthalen-2-yl)-1,3-diphenylpropan-1-one；(3S)-3-naphthalen-2-yl-1,3-diphenylpropan-1-one
• CAS: 1383843-83-1
• 化学式: C₂₅H₂₀O
• 分子量: 336.433
• InChiKey: VVQJQDMDWBRYHJ-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  2-萘硼酸 、 反式-查耳酮 在 potassium fluoride 、 chlorobis(ethylene)rhodium(I) dimer 、 (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphine 作用下， 以 水 、 异丙醇 为溶剂， 反应 3.0h， 以99%的产率得到(+)-3-(naphthalen-2-yl)-1,3-diphenylpropan-1-one
  参考文献：
  名称：

  Rh/chiral sulfinylphosphine catalyzed asymmetric 1,4-addition of arylboronic acids to chalcones

  摘要：

  A general method to obtain enantioenriched 1,3,3-triarylpropan-1-ones bearing a diarylmethine stereocenter was developed using Rh/chiral sulfinylphosphine catalyzed 1,4-addition of arylboronic acids to chalcones. The catalysis progressed smoothly in the presence of 2 mol % catalyst formed in situ from [Rh(C2H4)(2)Cl](2) and chiral tert-butanesulfinylphosphine and gave the adducts with up to 99% yield and 98% ee. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.096

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