2-diphenylphosphinyl-2'-methoxybiphenyl | 402822-67-7

• 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: 2-diphenylphosphinyl-2'-methoxybiphenyl
• 英文别名: 2-(diphenylphosphinyl)-2'-methoxyl-1,1'-biphenyl；1-(2-Diphenylphosphorylphenyl)-2-methoxybenzene
• CAS: 402822-67-7
• 化学式: C₂₅H₂₁O₂P
• 分子量: 384.414
• InChiKey: YYTALYAHFXRUMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-diphenylphosphinyl-2'-methoxybiphenyl 在 三氯硅烷 、 三乙胺 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 5.0h， 以382 mg的产率得到2-二苯基膦-2’-甲氧基联苯
  参考文献：
  名称：

  Bifunctional phosphine-catalyzed cross-Rauhut–Currier/Michael/aldol condensation triple domino reaction: synthesis of functionalized cyclohexenes

  摘要：

  开发了一种新型双功能膦催化反应。交叉-劳胡特-库里尔（Cross-RauhutâCurrier）、迈克尔（Michael）和醛醇（ldol）反应被成功地组合成一个多米诺过程。这种方法为构建高度取代的环己烯骨架提供了一种强有力的方法。

  DOI：

  10.1039/c1ob05693j
• 作为产物：
  描述：

  2-二苯基膦-2’-甲氧基联苯 在 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 2-diphenylphosphinyl-2'-methoxybiphenyl
  参考文献：
  名称：

  Palladium-catalyzed R₂(O)P directed C(sp²)–H acetoxylation

  摘要：

  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。

  DOI：

  10.1039/c4cc01238k

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。
• P(O)R₂-Directed Enantioselective C–H Olefination toward Chiral Atropoisomeric Phosphine–Olefin Compounds
  作者：Shi-Xia Li、Yan-Na Ma、Shang-Dong Yang

  DOI：10.1021/acs.orglett.7b00608

  日期：2017.4.7

  An effective synthesis of chiral atropoisomeric biaryl phosphine-olefin compounds via palladium-catalyzed enantioselective C-H olefination has been developed for the first time. The reactions are operationally simple, tolerate wide functional groups, and have a good ee value, Notably, P(O)R-2 not only acts as the directing group to direct C-H activation in order to make a useful ligand but also serves to facilitate composition of the product in a useful manner in this transformation.
• Pd(II)-Catalyzed Ph₂(O)P-Directed C–H Olefination toward Phosphine–Alkene Ligands
  作者：Hong-Li Wang、Rong-Bin Hu、Heng Zhang、An-Xi Zhou、Shang-Dong Yang

  DOI：10.1021/ol402577p

  日期：2013.10.18

  The Pd(II)-catalyzed Ph-2(O)P-directed C-H olefination to synthesize alkene-phosphine compounds is reported. In contrast to previous examples of various directing groups that guide selective C-H activation, the Ph-2(O)P group not only acts as the directing group but also serves to construct the alkene-phosphine ligands. The monoprotected amino acid (MPAA) ligand Ac-Leu-OH is found to promote this reaction in a significant manner.
• Palladium-catalysed synthesis of biaryl phosphines
  作者：Colin Baillie、Jianliang Xiao

  DOI：10.1016/j.tet.2004.03.058

  日期：2004.5

  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.
• 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.