(E)-3-(2-(diphenylphosphino)phenyl)-1-phenylprop-2-en-1-one | 959140-93-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-3-(2-(diphenylphosphino)phenyl)-1-phenylprop-2-en-1-one
• 英文别名: (E)-3-(2-(diphenylphosphaneyl)phenyl)-1-phenylprop-2-en-1-one；(E)-3-(2-(diphenylphosphanyl)phenyl)-1-phenylprop-2-en-1-one；(E)-3-(2-diphenylphosphanylphenyl)-1-phenylpropenone；(2E)-3-[2-(Diphenylphosphino)phenyl]-1-phenyl-2-propen-1-one；(E)-3-(2-diphenylphosphanylphenyl)-1-phenylprop-2-en-1-one
• CAS: 959140-93-3
• 化学式: C₂₇H₂₁OP
• 分子量: 392.437
• InChiKey: LYSWQJAKKYBPDM-QZQOTICOSA-N

物化性质

• 熔点：
  117.2-117.7 °C
• 沸点：
  537.6±50.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-(diphenylphosphino)phenyl)-1-phenylprop-2-en-1-one 在 indium(III) chloride 、 sodium tetrahydroborate 作用下， 生成 3-(2-(diphenylphosphino)phenyl)-1-phenylpropan-1-one
  参考文献：
  名称：

  磷/缺乏电子的烯烃配体促进[Ar-Pd-C]还原消除的动力学研究

  摘要：

  在存在磷化氢/电子缺陷的烯烃配体的情况下，可以显着提高[Ar-Pd-C ]的还原消除速率。通过对2-碘代苯甲酸乙酯与烷基氯化锌的Negishi偶联进行系统动力学研究（参见方案），确定了[Ar-Pd-C ]的还原消除速率常数大于0.3 s -1，约为4或比以前报告的值大五个数量级。

  DOI：

  10.1002/chem.200802209
• 作为产物：
  描述：

  2-二苯基膦苯甲醛 、 苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以60 %的产率得到(E)-3-(2-(diphenylphosphino)phenyl)-1-phenylprop-2-en-1-one
  参考文献：
  名称：

  有机膦作为烷基转移梭，用于使用烷基卤化物对查尔酮进行直接 β-烷基化

  摘要：

  我们报告了一种有效的烷基转移策略，用于使用市售的烷基溴化物作为烷基试剂对查耳酮进行直接 β-烷基化。在这种转化中，查尔酮中的邻磷取代基对于控制其反应性和选择性至关重要。它还作为可靠的烷基转移梭，将亲电烷基溴化物转化为季鏻盐形式的亲核烷基物质，并将烷基有效地转移到查耳酮的 β-位。这种烷基转移策略可以进一步扩展到邻磷酰基苯甲醛的烯基化以组装功能化多烯。

  DOI：

  10.1021/acs.joc.2c02505
• 作为试剂：
  描述：

  苯甲酸甲酯 在 (E)-3-(2-(diphenylphosphino)phenyl)-1-phenylprop-2-en-1-one 、 tris-(dibenzylideneacetone)dipalladium(0) 、 copper(l) iodide 、 silver nitrate 、 三乙胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 8.17h， 生成 methyl 4-((naphthalen-2-yl)buta-1,3-diyn-1-yl)benzoate
  参考文献：
  名称：

  用于细胞成像的受 Fsp3 启发的拉曼探针的设计、合成和分析评估

  摘要：

  新标签已被开发用于受激拉曼散射 (SRS) 细胞成像，其 Fsp 3特性比现有替代品更高。这些含二炔的标签通过有效的 Pd 催化交叉偶联方法合成，并在成像前通过质谱 (MS) 关联研究和 X 射线晶体学进行分析。MS 数据显示聚集和 cLog P之间存在线性关系，而 X 射线实验表明修改影响了 π-π 堆积。

  DOI：

  10.1002/ejoc.202200393

文献信息

• Superior Effect of a π-Acceptor Ligand (Phosphine−Electron-Deficient Olefin Ligand) in the Negishi Coupling Involving Alkylzinc Reagents
  作者：Xiancai Luo、Heng Zhang、Hui Duan、Qiang Liu、Lizheng Zhu、Tony Zhang、Aiwen Lei

  DOI：10.1021/ol701995t

  日期：2007.10.1

  [GRAPHICS]Palladium-catalyzed Negishi cross-coupling involving primary and secondary alkyls, even in the presence of beta-H, can be achieved at ambient temperature using chelating ligands containing a phospline and an electron-deficient olefin. The superior effects of the ligands were shown not only in the desired cross-coupling product yields but also in the fast reaction at mild conditions. This reaction has been also scaled up to 50 g in 0.005 mol % catalyst (20,000 TONs) at room temperature.
• Ferrocenyl chalcones versus organic chalcones: A comparative study of their nematocidal activity
  作者：Saeed Attar、Zachary O’Brien、Hasan Alhaddad、Melissa L. Golden、Alejandro Calderón-Urrea

  DOI：10.1016/j.bmc.2011.01.048

  日期：2011.3

  A series of 30 organic chlacones and 33 ferrocenyl (Fc) chalcones were synthesized and characterized by melting point, elemental analysis, spectroscopy (H-1 NMR and FTIR) and, in two cases, by X-ray crystallography. The biological activity of each compound (10(-4) M in DMSO) against the model nematode Caenorhabditis elegans was examined in terms of % mortality (percent nematodes that died) and % fecundity (percent nematodes that reproduced) and compared to that obtained for the control medium (1% DMSO) over a 14-day period. Detailed conformational analyses for two Fc-chalcones (studied also by X-ray crystallography) were performed via molecular modeling studies. In general, the organic chalcones were found to be less polar than their Fc analogs. Some structure-activity relationships (SARs) were determined: (a) The nematocidal activities of the organic chalcones in this series were found to be much greater than those of their ferrocenyl analogs. (b) The position of the carbonyl group played a central role in the biological activity of both classes of chalcones studied. (c) For both classes of chalcones, lipophilicity of a compound seemed to play a significant role in its nematocidal activity. (d) The planarity of a ferrocenyl-chlacone seems to play a role in its activity. Published by Elsevier Ltd.
• Acceleration of Reductive Elimination of [Ar-Pd-C sp 3] by a Phosphine/Electron-Deficient Olefin Ligand: A Kinetic Investigation
  作者：Heng Zhang、Xiancai Luo、Kittiya Wongkhan、Hui Duan、Qiang Li、Lizheng Zhu、Jian Wang、Andrei S. Batsanov、Judith A. K. Howard、Todd B. Marder、Aiwen Lei

  DOI：10.1002/chem.200802209

  日期：2009.4.6

  Dramatic rate enhancement of reductive elimination of [Ar‐Pd‐C] was observed in the presence of a phosphine/electron‐deficient olefin ligand. Through systematic kinetic investigations of the Negishi coupling of ethyl 2‐iodobenzoate with alkylzinc chlorides (see scheme), the rate constants for reductive elimination of [Ar‐Pd‐C] were determined to be greater than 0.3 s−1, which is about four or five

  在存在磷化氢/电子缺陷的烯烃配体的情况下，可以显着提高[Ar-Pd-C ]的还原消除速率。通过对2-碘代苯甲酸乙酯与烷基氯化锌的Negishi偶联进行系统动力学研究（参见方案），确定了[Ar-Pd-C ]的还原消除速率常数大于0.3 s -1，约为4或比以前报告的值大五个数量级。
• Design, Synthesis, and Analytical Evaluation of Fsp ³ ‐Inspired Raman Probes for Cellular Imaging
  作者：Craig F. Steven、Martin Lee、Gary S. Nichol、Paul R. J. Davey、Elisabetta Chiarparin、Valerie G. Brunton、Alison N. Hulme

  DOI：10.1002/ejoc.202200393

  日期：2022.8.12

  New tags have been developed for stimulated Raman scattering (SRS) cellular imaging with increased Fsp3 character over existing alternatives. These diyne-containing tags were synthesised by an efficient Pd-catalysed cross-coupling methodology and analysed by mass spectrometry (MS) association studies and X-ray crystallography before imaging. MS data showed a linear relationship between aggregation

  新标签已被开发用于受激拉曼散射 (SRS) 细胞成像，其 Fsp 3特性比现有替代品更高。这些含二炔的标签通过有效的 Pd 催化交叉偶联方法合成，并在成像前通过质谱 (MS) 关联研究和 X 射线晶体学进行分析。MS 数据显示聚集和 cLog P之间存在线性关系，而 X 射线实验表明修改影响了 π-π 堆积。
• Organophosphine as an Alkyl Transfer Shuttle for the Direct β-Alkylation of Chalcones Using Alkyl Halides
  作者：Li-Jie Gu、Chao-Yang Li、Xin-Yue Niu、Xiong-Li Liu、Zhan-Wei Bu、Qi-Lin Wang

  DOI：10.1021/acs.joc.2c02505

  日期：2023.1.6

  this transformation, the ortho-phosphanyl substituent in the chalcones is crucial for controlling their reactivity and selectivity. It also serves as a reliable alkyl transfer shuttle to transform electrophilic alkyl bromides into nucleophilic alkyl species in the form of quaternary phosphonium salts and transfer the alkyl group effectively to the β-position of the chalcones. This alkyl transfer strategy

  我们报告了一种有效的烷基转移策略，用于使用市售的烷基溴化物作为烷基试剂对查耳酮进行直接 β-烷基化。在这种转化中，查尔酮中的邻磷取代基对于控制其反应性和选择性至关重要。它还作为可靠的烷基转移梭，将亲电烷基溴化物转化为季鏻盐形式的亲核烷基物质，并将烷基有效地转移到查耳酮的 β-位。这种烷基转移策略可以进一步扩展到邻磷酰基苯甲醛的烯基化以组装功能化多烯。