2-diphenylphosphinyl-4'-acetylbiphenyl | 402822-63-3

• 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: 2-diphenylphosphinyl-4'-acetylbiphenyl
• 英文别名: 1-[4-(2-Diphenylphosphorylphenyl)phenyl]ethanone
• CAS: 402822-63-3
• 化学式: C₂₆H₂₁O₂P
• 分子量: 396.425
• InChiKey: JONCPWDYSBMXSE-UHFFFAOYSA-N

物化性质

• 沸点：
  610.2±47.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-diphenylphosphinyl-4'-acetylbiphenyl 在 三氯硅烷 、 双氧水 、 palladium diacetate 、 三乙胺 作用下， 以 水 、 甲苯 为溶剂， 反应 12.5h， 生成 3-acetyl-5-phenyl-5H-dibenzophosphole 5-oxide
  参考文献：
  名称：

  钯催化三芳基膦通过碳氢键和碳磷键的裂解直接合成磷衍生物

  摘要：

  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）。

  DOI：

  10.1002/anie.201307115
• 作为产物：
  描述：

  二苯基膦 在 palladium diacetate 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ potassium phosphate 、 双氧水 、 sodium acetate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 85.0h， 生成 2-diphenylphosphinyl-4'-acetylbiphenyl
  参考文献：
  名称：

  Palladium-catalysed synthesis of biaryl phosphines

  摘要：

  Monodentate, biphenyl-type phosphines have emerged as a powerful class of ligands in homogeneous catalysis. Synthetic methods for these ligands are limited, however. We report that the palladium-catalysed Suzuki coupling of OPR2(o-C6H4X) (R=Ph, t-Bu; X=Br, I) with arylboronic acids affords a variety of biaryl phosphine oxides including those that contain heterocycles. The corresponding phosphines are readily obtained by treatment with HSiCl3. The methodology provides an easy entry to monodentate biaryl and heterobiaryl P<^>X (X=N, O, S) phosphines with diverse steric and electronic properties. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.058

文献信息

• Palladium-catalyzed R2(O)P-directed C(sp2)-H activation
  作者：Hongyu Zhang、Shangdong Yang

  DOI：10.1007/s11426-015-5382-1

  日期：2015.8

  In recent years, transition-metal-catalyzed inert C-H bond activation has developed rapidly and is a powerful protocol for the construction of new C-C or C-X bonds and the introduction of new functional groups. Our group has also developed a series of R2(O)P-directed Pd-catalyzed C-H functionalizations involving olefination, hydroxylation, acetoxylation, arylation, and acylation through an uncommon seven-membered cyclo-palladium pretransition state. Unlike previously used directing groups, the R2(O)P group acts as a directing group and is also involved in the construction of P,-hetero-ligands.

  近年来，过渡金属催化的惰性C-H键活化发展迅速，是构建新的C-C或C-X键和引入新官能团的有力途径。我们课题组也发展了一系列R2(O)P导向的Pd催化C-H官能化反应，包括烯化、羟基化、醋酸化、芳基化和酰基化，通过一个罕见的七元环钯前过渡态。与先前使用的导向基团不同，R2(O)P基团既作为导向基团又参与构建P,-杂配体。
• Palladium-catalyzed R₂(O)P directed C(sp²)–H acetoxylation
  作者：Heng Zhang、Rong-Bin Hu、Xiao-Yu Zhang、Shi-Xia Li、Shang-Dong Yang

  DOI：10.1039/c4cc01238k

  日期：——

  A novel and efficient Pd-catalyzed C–H acetoxylation is described. The approach uses R₂(O)P as a directing group to synthesize various substituted 2′-phosphoryl biphenyl-2-OAc compounds.

  描述了一种新颖高效的钯催化的C-H乙酰化方法。该方法使用R₂(O)P作为导向基团，合成各种取代的2'-磷酸酯联苯-2-OAc化合物。
• Electrochemical oxidative intramolecular annulation of aryl phosphine compounds: an efficient approach for synthesizing π-conjugated phosphonium salts
  作者：Tianmei Zhang、Min Cai、Wenfeng Zhao、Mao Liu、Nan Jiang、Qingmei Ge、Hang Cong

  DOI：10.1039/d2gc04569a

  日期：——

  A practical and efficient electrochemical approach for the synthesis of π-conjugated phosphonium salts via intramolecular annulation and the construction of the C–P bond is developed. This reaction proceeded under catalyst- and adscititious oxidant-free conditions at room temperature. A series of substituted π-conjugated phosphonium salt products were obtained with good functional group tolerance and

  开发了一种实用且有效的电化学方法，用于通过分子内环化和 C-P 键的构建来合成 π-共轭鏻盐。该反应在室温下在无催化剂和无外加氧化剂的条件下进行。获得了一系列具有良好官能团耐受性和产率的取代π-共轭鏻盐产物。进行了克级反应以证明该协议在实际应用中的潜力。初步的机理研究表明自由基被认为参与了这一过程。
• Synthesis of biphenyl-based phosphines by Suzuki coupling
  作者：Colin Baillie、Weiping Chen、Jianliang Xiao

  DOI：10.1016/s0040-4039(01)01981-5

  日期：2001.12

  A series of phosphine oxides has been synthesised by the palladium-catalysed Suzuki coupling of arylboronic acids with OPPh2(o-C6H4Br). Oil reduction with trichlorosilane. functionalised. biphenyl-based phosphine ligands were obtained in good yields. Our preliminary results indicate these ligands to be effective for palladium-catalysed C-C coupling reactions including the formation of their own oxides. (C) 2001 Elsevier Science Ltd. All rights reserved.