4-(diphenylphosphino)benzylamine | 201011-40-7

• 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: 4-(diphenylphosphino)benzylamine
• 英文别名: (4-Diphenylphosphanylphenyl)methylamine；(4-diphenylphosphanylphenyl)methanamine
• CAS: 201011-40-7
• 化学式: C₁₉H₁₈NP
• 分子量: 291.332
• InChiKey: FZHGPBPGIHUNAH-UHFFFAOYSA-N

物化性质

• 沸点：
  414.0±28.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(diphenylphosphino)benzylamine 在 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 2-[(4-Diphenylphosphanylphenyl)methylcarbamoylamino]acetic acid
  参考文献：
  名称：

  Noncovalently Functionalized Dendrimers as Recyclable Catalysts

  摘要：

  The efficient reversible functionalization of the periphery of urea adamantyl poly(propylene imine) dendrimers with catalytic sites using noncovalent interactions is described. Phosphine ligands equipped with urea acetic groups, a binding motive complementary to that of the dendrimer host, have been prepared and assembled to the dendrimer support. The resulting supramolecular complex has been used as a multidentate ligand system in the palladium-catalyzed allylic amination reaction in a batch process and in a continuous-flow membrane reactor. We found that the activity and selectivity of the dendrimeric complex is similar to that of the monomer complex, which indicates that the catalytic centers act as independent sites. The size of the supramolecular system is sufficiently large and the binding of the guests is strong enabling a good separation of the catalyst components from the reaction mixture using nanofiltration techniques.

  DOI：

  10.1021/ja005774u
• 作为产物：
  描述：

  4-二苯基膦苯甲酸 在 lithium aluminium tetrahydride 、 六氯环三磷腈 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 2.67h， 生成 4-(diphenylphosphino)benzylamine
  参考文献：
  名称：

  First Fluorescent Photoinduced Electron Transfer (PET) Reagent for Hydroperoxides

  摘要：

  graphicA novel fluorescent reagent for hydroperoxides, 4-(2-diphenylphosphinoethylamino)-7-nitro-2,1,3-benzoxadiazole (1), was developed on the basis of the method for designing photoinduced electron transfer (PET) reagents having a benzofurazan skeleton. Compound 1 was quantitatively reacted with hydroperoxides to give its fluorescent derivative, 2. In acetonitrile, the Phi value (0.44) of 2 was 31 times greater than that of 1. The long excitation (458 nm) and emission (520 nm) wavelengths of 2 are suitable for the determination of hydroperoxides, especially in biosamples.

  DOI：

  10.1021/ol0342150

文献信息

• Phosphorus Functionalized Dendrimers and Hyperbranched Polymers: Is There a Need for Perfect Dendrimers in Catalysis?
  作者：Fabrizio Ribaudo、Piet W. N. M. Van Leeuwen、Joost N. H. Reek

  DOI：10.1560/ijc.49.1.79

  日期：2009.5

  In this paper we describe the facile and straightforward covalent functionalization of commercially available dendritic poly(propylenimine) and hyper‐branched poly(ethylenimine) with P‐containing functional groups. The P‐functionalized macromolecules have been applied as multivalent ligands in the Pd‐catalyzed allylic substitution reactions (batch and continuous process) using either morpholine or thiophenol as nucleophile. Palladium complexes of all described molecules are active in allylic substitution reactions. The PEI functionalized polymers appear more sensitive to small changes in the P/Pd ratio than the PPI analogues, but form catalysts that are more active. When used in a continuous flow process the macromolecules are completely retained by the nanofiltration membrane, while the catalytic activity decreases with time because of palladium depletion. This is more severe for the allylic thiolation, probably because of the stronger affinity of sulfur for palladium, facilitating palladium leaching.

  摘要 本文介绍了用含 P 的官能团对市售树枝状聚（丙烯亚胺）和超支化聚（乙烯亚胺）进行简便直接的共价官能化。含 P 官能团的大分子已作为多价配体应用于以吗啉或噻吩酚为亲核体的钯催化烯丙基取代反应（间歇和连续过程）中。所有所述分子的钯配合物在烯丙基取代反应中都很活跃。与 PPI 类似物相比，PEI 功能化聚合物似乎对 P/Pd 比率的微小变化更为敏感，但形成的催化剂活性更高。在连续流工艺中使用时，大分子会被纳滤膜完全截留，而催化活性则会随着时间的推移而降低，这是因为钯耗竭的缘故。烯丙基硫醇化的情况更为严重，这可能是因为硫与钯的亲和力更强，有利于钯的沥滤。
• Zn(ii) Robson macrocycles as templates for chelating diphosphines
  作者：Sergio Ponsico、Henrik Gulyas、Marta Martínez-Belmonte、Eduardo C. Escudero-Adán、Zoraida Freixa、Piet W. N. M. van Leeuwen

  DOI：10.1039/c1dt10905g

  日期：——

  templated diphosphines cis-PtCl2 complexes were identified by NMR. The in situ assembled diphosphines showed a chelating effect in the rhodium catalyzed hydroformylation of 1-octene. Combination of Zn-RMC 3 and phosphine A gave the highest l/b ratio (13) in acetonitrile.

  螯合二膦是用双核锌（II）Robson大环（Zn-RMC）的复合物作为模板。金属中心（路易斯酸）与阴离子和中性路易斯碱官能化的单膦之间的相互作用驱动组装过程。最终结构的稳定性取决于对位膦的官能团的几何形状和亲和力以及RMC的结构。在游离配体中，根据X射线衍射，如几个组装体的分子结构所示，二位膦在假平面大环的相对面上进行配位。通过将磷原子配位到过渡金属中心来对系统进行预组织，从而可以在RMC的同一面上强制官能团的配位。对于几种模板化的二膦顺式-PtCl 2通过NMR鉴定复合物。的原位组装二膦显示出的铑催化加氢甲酰化的螯合效果1-辛烯。Zn-RMC 3和磷化氢A的组合在L / b比值最高的情况下（13）乙腈。
• Triphenylphosphine derivative, production process therefor, palladium complex thereof, and process for producing biaryl derivative
  申请人：——

  公开号：US20030065208A1

  公开（公告）日：2003-04-03

  Provided are a novel triphenyl phosphine derivative synthesized from a triphenylphosphine and a hydroxy-containing lactone; a palladium and a nickel complexes comprising the derivative as a ligand; and a process for preparing a biaryl derivative using the complex as a catalyst. A product can be easily separated from a catalyst or a phosphorus compound, and biaryl derivative can be synthesized in a higher yield, by using the complex of the present invention as a catalyst.

  提供了一种新型的三苯基膦衍生物，通过三苯基膦和含羟基的内酯合成；一种以该衍生物为配体的钯和镍配合物；以及一种利用该配合物作为催化剂制备联苯衍生物的方法。通过使用本发明的复合物作为催化剂，产品可以很容易地与催化剂或磷化合物分离，联苯衍生物可以以更高的产率合成。
• Catalytic Asymmetric C–H Arylation of (η⁶-Arene)Chromium Complexes: Facile Access to Planar-Chiral Phosphines
  作者：María Batuecas、Junfei Luo、Ivana Gergelitsová、Katrina Krämer、Daniel Whitaker、Iñigo J. Vitorica-Yrezabal、Igor Larrosa

  DOI：10.1021/acscatal.9b00918

  日期：2019.6.7

  hemilabile ligand H8-BINAP(O) is key to providing high enantioselectivity in this transformation. We show that this methodology opens the door to the synthesis of a variety of planar-chiral chromium derivatives which can be easily transformed into planar chiral mono- or diphosphines. Mechanistic studies, including synthesis and characterization of Pd and Ag complexes and their detection in the reaction mixture

  报道了（η6-芳烃）铬配合物的催化不对称直接CH芳基化反应以获得平面手性化合物。半不稳定配体H8-BINAP（O）的使用是在此转化过程中提供高对映选择性的关键。我们表明，该方法学为各种平面-手性铬衍生物的合成打开了大门，这些衍生物可以很容易地转化为平面的手性单膦或二膦。包括Pd和Ag配合物的合成和表征以及它们在反应混合物中的检测在内的机理研究表明，Pd催化/ Ag促进的催化系统由Ag进行CH活化步骤。
• Catalysis with Gold Complexes Immobilised on Carbon Nanotubes by π-π Stacking Interactions: Heterogeneous Catalysis versus the Boomerang Effect
  作者：Charles Vriamont、Michel Devillers、Olivier Riant、Sophie Hermans

  DOI：10.1002/chem.201300998

  日期：2013.9.2

  supported homogeneous catalyst. The heterogenised catalyst and its homogeneous counterpart exhibited similar activity in a range of enyne cyclisation reactions. Bearing in mind that π–π interactions are affected by temperature and solvent polarity, the reuse and robustness of the supported homogeneous catalyst was tested to explore the scope and limitations of the recyclability of this catalyst. Under

  一种新型标记的金（I）配合物已被合成并作为均相催化剂进行了测试。首先，通过使用不同的溶剂优化反应条件，选择简单的1,6-烯炔作为环化的模型底物。然后研究了我们通过pyr-π堆积相互作用将标记的金络合物非共价固定在多壁碳纳米管上的方法，以获得负载型均相催化剂。在一系列烯炔环化反应中，异相催化剂及其均相对应物表现出相似的活性。考虑到π-π相互作用受温度和溶剂极性的影响，对负载型均相催化剂的重用性和耐用性进行了测试，以探索该催化剂可回收性的范围和局限性。在优化的条件下，