(-)-3-(4-chlorophenyl)-1,3-diphenylpropan-1-one | 1338350-53-0

• 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-chlorophenyl)-1,3-diphenylpropan-1-one
• CAS: 1338350-53-0
• 化学式: C₂₁H₁₇ClO
• 分子量: 320.818
• InChiKey: APVMTRRHXKZDIN-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

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-chlorophenyl)-1,3-diphenylpropan-1-one 、 (S)-3-(4-chlorophenyl)-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

• Enantioselective Conjugate Addition of Stabilized Arylzinc Iodide to Enones: an Improved Protocol of the Hayashi Reaction
  作者：Gianluca Casotti、Vincenzo Rositano、Anna Iuliano

  DOI：10.1002/adsc.202001141

  日期：2021.2.16

  Stabilised arylzinc iodide, prepared by direct insertion of zinc into aryl iodides, were used as nucleophiles in the Hayashi Rh‐catalysed enantioselective conjugate addition to enones. The reaction conditions were optimized in the addition of phenylzinc iodide to 2‐cyclohexen‐1‐one, obtaining good yields and 99% ee of the addition product. The general applicability of the protocol was checked using

  通过将锌直接插入芳基碘化物中制备的稳定的芳基碘化碘化物被用作Hayashi Rh催化的烯酮对映体选择性共轭物的亲核试剂。优化了反应条件，将苯碘化锌添加到2-环己烯-1-酮中，获得了良好的收率和99％ee的加成产物。使用不同的芳基碘化碘和烯酮检查方案的一般适用性。具有卤素和亲电基团的有机金属试剂也已成功使用。
• Cage‐Shaped Phosphites Having <i>C</i>₃‐Symmetric Chiral Environment: Steric Control of Lewis Basicity and Application as Chiral Ligands in Rhodium‐Catalyzed Conjugate Additions
  作者：Xiao Liu、Kazuma Tomita、Akihito Konishi、Makoto Yasuda

  DOI：10.1002/chem.202302611

  日期：2023.12

  cage-shaped phosphites were developed as a new type of chiral ligand. Their Lewis basicity and chiral environment are precisely controlled by the tethered group. The cage-shaped phosphites successfully worked as chiral ligands in Rh-catalyzed asymmetric conjugate additions, realizing acceptable yields with excellent enantioselectivity, and were used to synthesize a pharmacologically important molecule

  C 3 -对称手性笼状亚磷酸酯被开发为一种新型手性配体。它们的路易斯碱度和手性环境由束缚基团精确控制。笼状亚磷酸酯成功地作为Rh催化的不对称共轭加成中的手性配体，实现了可接受的产率和优异的对映选择性，并用于合成药理学上重要的分子。
• 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
• Rh/chiral sulfinylphosphine catalyzed asymmetric 1,4-addition of arylboronic acids to chalcones
  作者：Guihua Chen、Junwei Xing、Peng Cao、Jian Liao

  DOI：10.1016/j.tet.2012.04.096

  日期：2012.7

  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.