2-methyl-5-phenyl-5H-dibenzophosphole 5-oxide | 1332483-75-6

• 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: 2-methyl-5-phenyl-5H-dibenzophosphole 5-oxide
• 英文别名: 2-methyl-5-phenyldibenzophosphole 5-oxide；2-Methyl-5-phenylbenzo[b]phosphindole 5-oxide
• CAS: 1332483-75-6
• 化学式: C₁₉H₁₅OP
• 分子量: 290.301
• InChiKey: MJDXTDPYHXQANH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-bromo-1-(diphenylphosphinoyl)-4-methylbenzene 在 palladium diacetate 、 potassium carbonate 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 以85%的产率得到2-methyl-5-phenyl-5H-dibenzophosphole 5-oxide
  参考文献：
  名称：

  钯-邻卤代二芳基膦氧化物的分子内直接芳基化反应合成二苯并膦氧化物

  摘要：

  开发了钯催化的分子内直接芳基化反应，还实现了两个有效的单锅顺序直接芳基化/ Suzuki-Miyaura偶联和分子内/分子间直接芳基化反应。该方法为从易于获得的邻卤代二芳基膦氧化物合成并进一步官能化二苯并膦氧化物提供了一个简单而直接的程序，收率很高。

  DOI：

  10.1002/adsc.201301081

文献信息

• Palladium-Catalyzed Direct Synthesis of Phosphole Derivatives from Triarylphosphines through Cleavage of Carbon-Hydrogen and Carbon-Phosphorus Bonds
  作者：Katsuaki Baba、Mamoru Tobisu、Naoto Chatani

  DOI：10.1002/anie.201307115

  日期：2013.11.4

  (Phosp)hole in one: A palladium‐catalyzed synthesis for directly assembling phosphole skeletons from triarylphosphines through CH and CP bond cleavage was developed. This approach overcomes several of the limitations of the so far reported methods. Phospholes bearing a range of functionalities (including Br, F, CO2Me, Ac, and CN) and an array of fused rings (naphthalenes, anthracenes, furans, and

  在一个（Phosp）孔：一个钯催化合成的用于从至C三芳基膦直接组装磷杂环骨架 H和13 C  P键裂解被开发。这种方法克服了迄今为止报道的方法的一些局限性。可以容易地合成具有一系列功能性（包括Br，F，CO 2 Me，Ac和CN）的磷脂和一系列稠环（萘，蒽，呋喃和吡咯）。
• Palladium-Catalyzed Synthesis of Dibenzophosphole Oxides via Intramolecular Dehydrogenative Cyclization
  作者：Yoichiro Kuninobu、Takuya Yoshida、Kazuhiko Takai

  DOI：10.1021/jo201030j

  日期：2011.9.16

  Dibenzophosphole oxides were obtained from secondary hydrophosphine oxides with a biphenyl group by dehydrogenation via phosphine–hydrogen and carbon–hydrogen bond cleavage in the presence of a catalytic amount of palladium(II) acetate, Pd(OAc)2. By using this reaction, a ladder-type dibenzophosphole oxide could also be synthesized by double intramolecular dehydrogenative cyclization.

  在催化量的乙酸钯（II）Pd（OAc）2存在下，通过膦-氢和碳-氢键的裂解，从具有联苯基的仲氢氧化膦中获得二苯并磷氧化物。通过使用该反应，也可以通过分子内双脱氢环化来合成梯型二苯甲酰氧化物。
• Synthesis of Dibenzophospholes by Tf₂O-Mediated Intramolecular Phospha-Friedel–Crafts-Type Reaction
  作者：Kazutoshi Nishimura、Koji Hirano、Masahiro Miura

  DOI：10.1021/acs.orglett.9b00219

  日期：2019.3.1

  A Tf2O-mediated intramolecular phospha-Friedel–Crafts-type reaction of secondary biarylphosphine oxides has been developed. The reaction is promoted simply by Tf2O to form the corresponding dibenzophospholes under metal-free conditions. The starting substrates are readily available and easy-to-handle phosphine oxides, and the regioselectivity is controlled by the innate electronic nature. Thus, this

  二次联芳基膦氧化物的Tf 2 O介导的分子内膦-弗里德尔-克来福特型反应已得到开发。在没有金属的条件下，Tf 2 O可以简单地促进反应形成相应的二苯并膦。起始底物容易获得且易于处理的氧化膦，并且区域选择性由固有的电子性质控制。因此，该新开发的方案可以为材料化学中具有浓厚兴趣的高度π共轭二苯并膦提供简明和互补的方法。
• Heterocyclic compound and organic light emitting device including the same
  申请人：Samsung Display Co., Ltd.

  公开号：US11078210B2

  公开（公告）日：2021-08-03

  A a heterocyclic compound and an organic light-emitting device including the same are presented. The organic light-emitting device includes two electrodes and an organic layer between the electrodes that includes an emission layer and at least one heterocyclic compound, which is represented by the following Formula: wherein ring A1 is selected from a C5-C60 carbocyclic group and a C1-C60 heterocyclic group, X1 is O, S, or Se, and Li is selected from a substituted or unsubstituted C5-C60 carbocyclic group, a substituted or unsubstituted C1-C60 heterocyclic group, *—Si(Q1)(Q2)-*′, *—P(═O)(Q1)-*′, *—P(═O)2—*′, *—P(═S)(Q1)-*′, *—P(═S)2—*′, *—S(═O)(Q1)-*′, and *—S(═O)2—*′. Other variables in the Formula are defined, and more specific structures are disclosed in the specification.

  本文介绍了一种杂环化合物和包括该杂环化合物的有机发光器件。有机发光器件包括两个电极和电极之间的有机层，有机层包括发射层和至少一种杂环化合物，杂环化合物用下式表示： 其中环 A1 选自 C5-C60 碳环基团和 C1-C60 杂环基团，X1 是 O、S 或 Se，Li 选自取代或未取代的 C5-C60 碳环基团、取代或未取代的 C1-C60 杂环基团、*-Si(Q1)(Q2)-*′、*-P(═O)(Q1)-*′、*-P(═O)2-*′、*-P(═S)(Q1)-*′、*-P(═S)2-*′、*-S(═O)(Q1)-*′和*-S(═O)2-*′。公式中的其他变量已定义，更具体的结构已在说明书中披露。
• HETEROCYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
  申请人：Samsung Display Co., Ltd.

  公开号：US20190248801A1

  公开（公告）日：2019-08-15

  A a heterocyclic compound and an organic light-emitting device including the same are presented. The organic light-emitting device includes two electrodes and an organic layer between the electrodes that includes an emission layer and at least one heterocyclic compound, which is represented by the following Formula: wherein ring A 1 is selected from a C 5 -C 60 carbocyclic group and a C 1 -C 60 heterocyclic group, X 1 is O, S, or Se, and Li is selected from a substituted or unsubstituted C 5 -C 60 carbocyclic group, a substituted or unsubstituted C 1 -C 60 heterocyclic group, *—Si(Q 1 )(Q 2 )-*′, *—P(═O)(Q 1 )-*′, *—P(═O) 2 —*′, *—P(═S)(Q 1 )-*′, *—P(═S) 2 —*′, *—S(═O)(Q 1 )-*′, and *—S(═O) 2 —*′. Other variables in the Formula are defined, and more specific structures are disclosed in the specification.