furan-2-yldiphenylphosphine oxide | 40927-85-3

• 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: furan-2-yldiphenylphosphine oxide
• 英文别名: 2-Furyldiphenylphosphinoxid；2-Diphenylphosphorylfuran
• CAS: 40927-85-3
• 化学式: C₁₆H₁₃O₂P
• 分子量: 268.252
• InChiKey: GTCAMARQDSZEOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  生成 furan-2-yldiphenylphosphine oxide
  参考文献：
  名称：

  Electronic Properties of Furyl Substituents at Phosphorus and Their Influence on ³¹P NMR Chemical Shifts

  摘要：

  The electronic properties of 2-furyl and 3-furyl substituents attached to phosphanes and phosphonium salts were studied by means of IR spectroscopy and experimental and computational P-31 NMR spectroscopy. The heteroaromatic systems proved to be electron withdrawing with respect to phenyl substituents. However, phosphorus atoms with attached furyl substituents are strongly shielded in NMR. The reason for this phenomenon was studied by solid state P-31 MAS NMR experiments. The chemical shift tensor was extracted, and the orientation within the molecules was determined. The tensor component sigma(33), which is effected the most by furyl systems, is oriented perpendicular to the P-C bonds of the substituents. P-furyl bonds are shorter than P-phenyl bonds. We assume therefore a lower ground-state energy of the molecules, because of the electron withdrawing properties of the 2-furyl systems. The sigma(para) component of the P-31 NMR magnetic shielding is therefore smaller, which results in an overall increase of the magnetic shielding.

  DOI：

  10.1021/ja057085u

文献信息

• Decarbonylative C–P Bond Formation Using Aromatic Esters and Organophosphorus Compounds
  作者：Ryota Isshiki、Kei Muto、Junichiro Yamaguchi

  DOI：10.1021/acs.orglett.8b00080

  日期：2018.2.16

  Ni-catalyzed C–P bond formation was achieved using aromatic esters as unconventional aryl sources. The key to success was the use of a thiophene-based diphosphine ligand (dcypt). Several aromatic esters including heteroaromatics can be coupled with phosphine oxides and phosphates, providing aryl phosphorus compounds. The synthetic utility of the method was demonstrated by application of the present

  镍催化的C-P键的形成是通过使用芳族酯作为非常规的芳基来实现的。成功的关键是使用基于噻吩的二膦配体（dcypt）。可以将包括杂芳族化合物在内的几种芳族酯与氧化膦和磷酸酯偶联，提供芳基磷化合物。通过将本方案应用于顺序偶合反应，证明了该方法的综合实用性。
• Nickel-catalyzed C–P cross-coupling of (het)aryl tosylates with secondary phosphine oxides
  作者：Xiao-Yun He

  DOI：10.1177/1747519821994533

  日期：2021.7

  A novel and convenient approach to the synthesis of various tertiary phosphine oxides via nickel-catalyzed cross-coupling of (het)aromatic tosylates with secondary phosphine oxides is developed. The reaction employs cheap nickel as the catalyst, 1-(2-(di-tert-butylphosphanyl)phenyl)-4-methoxypiperidine (L3) as the ligand, and pyridine as the base. This reaction produces the corresponding (het)aromatic

  通过一种镍催化的（杂）芳族甲苯磺酸酯与仲膦氧化物的交叉偶联反应，开发了一种新颖，方便的合成各种叔膦氧化物的方法。该反应使用廉价的镍作为催化剂，使用1-（2-（二叔丁基膦酰基）苯基）-4-甲氧基哌啶（L3）作为配体，并使用吡啶作为碱。该反应以高至高产率产生相应的（杂）芳族磷化合物。而且，在该方法中报道了四种新的叔膦氧化物。
• Mn-Catalyzed Electrooxidative Undirected C–H/P–H Cross-Coupling between Aromatics and Diphenyl Phosphine Oxides
  作者：Siyuan Wang、Qilin Xue、Zhipeng Guan、Yayu Ye、Aiwen Lei

  DOI：10.1021/acscatal.1c00549

  日期：2021.4.2

  in C–P bond formation since it requires no pretreatment of substrates. Herein, we reported a Mn-catalyzed electrochemical intermolecular dehydrogenative cross-coupling between aryl C–H and diphenyl phosphine oxides. In undivided cells, a series of phosphorylation or diphosphorylation products could be obtained separately by adjusting the proportion of substrates. A catalytic amount of inexpensive Mn(II)

  C-P键广泛存在于许多生物活性化合物和功能分子中。过渡金属催化的脱氢C–H / P–H交叉偶联在C–P键的形成中起着至关重要的作用，因为它不需要对底物进行预处理。在本文中，我们报道了芳基CH和二苯基氧化膦之间Mn催化的电化学分子间脱氢交叉偶联。在未分裂的细胞中，可以通过调节底物的比例分别获得一系列的磷酸化或二磷酸化产物。使用了催化量的廉价Mn（II）盐，在此过程中不需要外部化学氧化剂。动力学同位素效应实验表明，CH活化不是决定速率的步骤。
• A Wittig Reaction with 2-Furyl Substituents at the Phosphorus Atom: Improved (Z) Selectivity and Isolation of a Stable Oxaphosphetane Intermediate
  作者：Marco Appel、Steffen Blaurock、Stefan Berger

  DOI：10.1002/1099-0690(200204)2002:7<1143::aid-ejoc1143>3.0.co;2-g

  日期：2002.4

  Wittig reactions with ylides bearing one, two or three 2-furyl groups directly bound to the phosphorus atom have been studied. Greatly improved (Z)-alkene selectivities of up to 98:2 could be observed if 2-furyl groups were present. Monitoring of the reactions by NMR spectroscopy revealed only oxaphosphetane intermediates, which became more stable with increasing number of 2-furyl substituents bound

  已经研究了与带有一个、两个或三个直接与磷原子结合的 2-呋喃基的叶立德的 Wittig 反应。如果存在 2-呋喃基，则可以观察到高达 98:2 的 (Z)-烯烃选择性大大提高。通过 NMR 光谱对反应的监测显示只有氧代膦烷中间体，随着与磷原子结合的 2-呋喃基取代基数量的增加，中间体变得更加稳定。Oxaphosphetane 10d 与三个呋喃基团被成功分离，并提供了晶体结构分析的结果。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
• THIN FILM AND COMPOUND USED IN THE SAME
  申请人：Ohshita Joji

  公开号：US20130001472A1

  公开（公告）日：2013-01-03

  To provide a novel material exhibiting excellent light-emitting characteristics using a heavy metal element having relatively abundant reserve. A thin film containing a compound of Formula (1): wherein Ar 1 and Ar 2 are each independently a C 3-30 aromatic ring; R 1 and R 2 are a substituent; a and b are each independently an integer of 0 to 12, wherein when a is 2 or more, each R 1 is optionally different from each other and two R 1 are optionally bonded with each other to form a ring structure, and when b is 2 or more, each R 2 is optionally different from each other and two R 2 are optionally bonded with each other to form a ring structure; A 1 is any of direct bond, —O—, —S—, —S(═O)—, —S(═O) 2 —, —PR 3 —, —NR 4 —, and —C(—R 5 ) 2 —; R 3 is a hydrogen atom or a substituent; R 4 is a hydrogen atom or a substituent; R 5 is a hydrogen atom or a substituent and two R 5 are optionally different from each other; E 1 is a monovalent group having 50 or less carbon atoms; L 1 is a ligand having 50 or less carbon atoms; c is an integer of 0 to 3, wherein when c is 2 or more, each L 1 is optionally different from each other; and each combination of a combination of E 1 and Ar 1 and a combination of E 1 and Ar 2 optionally forms a bond; and when c is 1 to 3, each combination of a combination of L 1 and E 1 , a combination of L 1 and Ar 1 , a combination of L 1 and Ar 2 , and a combination of L 1 and L 1 optionally forms a bond.

  提供一种使用相对丰富的重金属元素制备出具有优异发光特性的新型材料。所述薄膜包含式（1）的化合物：其中Ar1和Ar2各自独立为C3-30芳香环；R1和R2为取代基；a和b各自独立为0至12的整数，当a为2或更多时，每个R1可选择不同，两个R1可选择相互连接形成环状结构；当b为2或更多时，每个R2可选择不同，两个R2可选择相互连接形成环状结构；A1为直接键，-O-，-S-，-S(═O)-，-S(═O)2-，-PR3-，-NR4-和-C(—R5)2-中的任意一种；R3为氢原子或取代基；R4为氢原子或取代基；R5为氢原子或取代基，两个R5可选择不同；E1为具有50个或更少碳原子的一价基团；L1为具有50个或更少碳原子的配体；c为0至3的整数，当c为2或更多时，每个L1可选择不同；当c为1至3时，每个L1和E1的组合，每个L1和Ar1的组合，每个L1和Ar2的组合，以及每个L1和L1的组合可选择相互连接。