3-(4-bromophenyl)-1,3-diphenylpropan-1-one | 1338350-54-1

• 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-(4-bromophenyl)-1,3-diphenylpropan-1-one
• 英文别名: (R)-3-(4-bromophenyl)-1,3-diphenylpropan-1-one；(3R)-3-(4-bromophenyl)-1,3-diphenylpropan-1-one
• CAS: 1338350-54-1
• 化学式: C₂₁H₁₇BrO
• 分子量: 365.269
• InChiKey: WTKRBWMQAHGKHB-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  苯硼酸 在 (S)-3,3'-dichloro-2,2'-dihydroxy-1,1'-binaphthyl 作用下， 以 氯仿 为溶剂， 反应 48.0h， 生成 3-(4-bromophenyl)-1,3-diphenylpropan-1-one 、 (S)-3-(4-bromophenyl)-1,3-diphenylpropan-1-one
  参考文献：
  名称：

  Binaphthol-Catalyzed Asymmetric Conjugate Arylboration of Enones

  摘要：

  Conjugate addition of arylboronates to alpha,beta-unsaturated ketones may be catalyzed by chiral binaphthols with enantioselectivities of up to 99:1. Best results were observed with 3,3'-dichloro-BINOL. This chemistry was applied to syntheses of intermediates for syntheses of (+)-indatraline and (+)-tolterodine.

  DOI：

  10.1021/ol202391r

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
• Binaphthol-Catalyzed Asymmetric Conjugate Arylboration of Enones
  作者：Heather M. Turner、Jignesh Patel、Nootaree Niljianskul、J. Michael Chong

  DOI：10.1021/ol202391r

  日期：2011.11.4

  Conjugate addition of arylboronates to alpha,beta-unsaturated ketones may be catalyzed by chiral binaphthols with enantioselectivities of up to 99:1. Best results were observed with 3,3'-dichloro-BINOL. This chemistry was applied to syntheses of intermediates for syntheses of (+)-indatraline and (+)-tolterodine.