1,3-diphenyl-3-(4-(trifluoromethyl)phenyl)propan-1-one | 1020172-03-5

• 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: 1,3-diphenyl-3-(4-(trifluoromethyl)phenyl)propan-1-one
• 英文别名: (3R)-1,3-diphenyl-3-[4-(trifluoromethyl)phenyl]propan-1-one
• CAS: 1020172-03-5
• 化学式: C₂₂H₁₇F₃O
• 分子量: 354.372
• InChiKey: SEQYYZVLVMMHIQ-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯硼酸酐 、 (2E)-1-phenyl-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one 在 (CuOTf)*toluene 、 (Ss,1S,1'S)-N-(1-cyclohexylethyl)-N-(1-tetralinyl)-1,1'-spirobiindan-2,2'-diylphosphoramidite 、 potassium acetate 作用下， 以 甲苯 为溶剂， 反应 30.0h， 以87%的产率得到1,3-diphenyl-3-(4-(trifluoromethyl)phenyl)propan-1-one
  参考文献：
  名称：

  使用铜催化剂将有机硼试剂不对称共轭加成到常见的烯酮中

  摘要：

  亚磷酰胺的铜配合物有效地催化芳基硼试剂向无环烯酮的不对称加成。重要的是，鉴定了稀有的芳基铜（I）的 1,4-插入，这直接导致了与 O 结合的铜烯醇化物。新机制与传统的有机铜（I）在烯酮上的氧化加成/还原消除有着根本的不同。

  DOI：

  10.1021/jacs.5b11441

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。
• Enantioselective β-C(sp³)–H arylation of amides<i>via</i>synergistic nickel and photoredox catalysis
  作者：Wu Zhang、Xiaomin Shu、Leitao Huan、Buqing Cheng、Haohua Huo

  DOI：10.1039/d1ob01774h

  日期：——

  An enantioselective benzylic β-C(sp3)–H arylation of amides via synergistic nickel and photoredox catalysis is reported. The C–H bond is activated by a bromine-radical-mediated C–H cleavage. This mild yet straightforward protocol provides arylation products in up to 96% yield and with up to 95% ee.

  报道了通过协同镍和光氧化还原催化对酰胺的对映选择性苄基 β-C(sp 3 )-H 芳基化。C-H 键被溴自由基介导的 C-H 裂解激活。这种温和而直接的方案可提供高达 96% 的收率和高达 95% ee 的芳基化产物。
• 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
• A first high enantiocontrol of an asymmetric tertiary carbon center attached with a fluoroalkyl group via Rh(I)-catalyzed conjugate addition reaction
  作者：Tsutomu Konno、Tomoo Tanaka、Tomotsugu Miyabe、Atsunori Morigaki、Takashi Ishihara

  DOI：10.1016/j.tetlet.2008.01.122

  日期：2008.3

  Treatment of fluoroalkylated electron-deficient olefins with various boronic acids in the presence of a catalytic amount of Rh(l) coordinated with (S)-BINAP in toluene/H2O at the reflux temperature for 3 h gave the corresponding conjugate addition products with high enantioselectivity in high yields. (C) 2008 Elsevier Ltd. All rights reserved.
• 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.