(4-bromophenethyl)diphenylphosphine | 1403619-49-7

• 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-bromophenethyl)diphenylphosphine
• 英文别名: (4-bromophenethyl)diphenylphosphane；2-(4-Bromophenyl)ethyl-diphenylphosphane；2-(4-bromophenyl)ethyl-diphenylphosphane
• CAS: 1403619-49-7
• 化学式: C₂₀H₁₈BrP
• 分子量: 369.241
• InChiKey: KNHJSUIKMHXDFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (4-bromophenethyl)diphenylphosphine 在 selenium 、 正丁基锂 作用下， 以 四氢呋喃 、 氘代氯仿 、 正己烷 为溶剂， 反应 5.84h， 生成
  参考文献：
  名称：

  An examination of the effects of borate group proximity on phosphine donor power in anionic (phosphino)tetraphenylborate ligands

  摘要：

  The ligand electron-donating abilities are compared among a series of monodentate, anionic (phosphino) tetraphenylborate phosphines [Ph4P][Ph2P-R-C6H4BPh3] (R = -C6H4-, -CH2-, -CH2CH2- or none), and their neutral counterparts Ph2PR (R = biphenyl, -CH2Ph, -CH2CH2Ph or Ph). Among the anionic ligands, the position of the tetraphenylborate group relative to the diphenylphosphino donor moiety was systematically varied in an effort to examine how its proximity impacts donor power. The donor power was determined by measuring the (3)1P-Se-77 coupling constant for the corresponding selenide of each phosphine ligand via P-31 NMR spectroscopy. The anionic ligands yield lower P-31-Se-77 coupling constants than those measured for their respective neutral counterparts. Moreover, the P-31-Se-77 coupling constants among the anionic ligands increase when the tetraphenylborate group is positioned further from the phosphorus centre. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.10.048
• 作为产物：
  描述：

  4-溴苯乙醇 在 N-溴代丁二酰亚胺(NBS) 、 potassium tert-butylate 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (4-bromophenethyl)diphenylphosphine
  参考文献：
  名称：

  An examination of the effects of borate group proximity on phosphine donor power in anionic (phosphino)tetraphenylborate ligands

  摘要：

  The ligand electron-donating abilities are compared among a series of monodentate, anionic (phosphino) tetraphenylborate phosphines [Ph4P][Ph2P-R-C6H4BPh3] (R = -C6H4-, -CH2-, -CH2CH2- or none), and their neutral counterparts Ph2PR (R = biphenyl, -CH2Ph, -CH2CH2Ph or Ph). Among the anionic ligands, the position of the tetraphenylborate group relative to the diphenylphosphino donor moiety was systematically varied in an effort to examine how its proximity impacts donor power. The donor power was determined by measuring the (3)1P-Se-77 coupling constant for the corresponding selenide of each phosphine ligand via P-31 NMR spectroscopy. The anionic ligands yield lower P-31-Se-77 coupling constants than those measured for their respective neutral counterparts. Moreover, the P-31-Se-77 coupling constants among the anionic ligands increase when the tetraphenylborate group is positioned further from the phosphorus centre. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.10.048

文献信息

• Catalyst- and solvent-free hydrophosphination and multicomponent hydrothiophosphination of alkenes and alkynes
  作者：Yanina Moglie、María José González-Soria、Iris Martín-García、Gabriel Radivoy、Francisco Alonso

  DOI：10.1039/c6gc00903d

  日期：——

  The hydrophosphination of carbon-carbon multiple bonds has been generally performed under acid, base or metal catalysis in different solvents. Herein, alkyl and alkenyl tertiary phosphines are obtained by the addition...

  碳-碳多键的氢磷酸化通常已经在不同溶剂中的酸，碱或金属催化下进行。在本文中，通过加成获得烷基和烯基叔膦。
• Tin-catalyzed hydrophosphination of alkenes
  作者：John P. W. Stelmach、Christine A. Bange、Rory Waterman

  DOI：10.1039/c5dt04272k

  日期：——

  Simple tin derivatives, Cp*2SnCl2 (1) and Ph2SnCl2 (2), catalyze the hydrophosphination of alkene substrates with diphenylphosphine. Competitive dehydrocoupling to give Ph4P2 was observed, but this side reaction can be mitigated when the catalysis is conducted under an H2 atmosphere. Efforts to prepare stable tin bis(phosphido) compounds commonly resulted in decomposition to Ph4P2. Lewis acidic inorganic

  简单的锡衍生物Cp * 2 SnCl 2（1）和Ph 2 SnCl 2（2）催化烯烃与二苯基膦的加氢磷酸化。观察到竞争性的脱氢偶联得到Ph 4 P 2，但是当在H 2气氛下进行催化时，该副反应可以减轻。制备稳定的双（锡）双锡锡化合物的努力通常导致分解为Ph 4 P 2。路易斯酸性无机锡化合物不显示脱氢偶联反应性。发现路易斯酸B（C 6 F 5）如图3所示，其能够进行烯烃的加氢磷酸化，但是在测试条件下效果较差。
• Catalyst-free hydrophosphination of alkenes in presence of 2-methyltetrahydrofuran: a green and easy access to a wide range of tertiary phosphines
  作者：Damien Bissessar、Julien Egly、Thierry Achard、Pascal Steffanut、Stéphane Bellemin-Laponnaz

  DOI：10.1039/c9ra04896k

  日期：——

  reaction that is free of base, acid and catalyst, using only 2-methyltetrahydrofuran as additive has been performed. A new family of mono-, di-, tri- and tetra-phosphines compounds are obtained in good to excellent yields by adding diphenylphosphine to alkenes, mono- and polyfunctional acrylics (based on acrylate and methacrylate motifs) and acrylamide substrates. Addition of four equivalent of bio-mass

  已经进行了不含碱、酸和催化剂的氢膦化反应，仅使用 2-甲基四氢呋喃作为添加剂。通过将二苯基膦添加到烯烃、单官能和多官能丙烯酸树脂（基于丙烯酸酯和甲基丙烯酸酯基体）和丙烯酰胺基材中，可以以良好至优异的产率获得一系列新的单、二、三和四膦化合物。将四当量的生物质衍生的 2-MeTHF 添加到反应介质中可以提高转化率和反应时间，并降低反应物对氧化的敏感性。这种简单、直接和原子经济的方法尊重绿色化学的原则。此外，在每种情况下，这种转化都显示出对反马尔科夫尼科夫产物的专有区域选择性。
• Photocatalytic Hydrophosphination of Alkenes and Alkynes Using Diphenylphosphine and Triamidoamine‐Supported Zirconium
  作者：Bryan T. Novas、Christine A. Bange、Rory Waterman

  DOI：10.1002/ejic.201801079

  日期：2019.3.31

  Reactions of alkene or alkyne with diphenylphosphine and catalytic [κ5‐N,N,N,N,C‐(Me3SiNCH2CH2)2NCH2CH2NSiMe2CH2]Zr (1) are greatly enhanced under photolysis, providing viable catalytic hydrophosphination with a broad substrate scope. Whereas diphenylphosphine had been an inaccessible substrate under thermal conditions, complete conversion of alkene substrates to tertiary phosphine is achieved in as

  与二苯膦和催化烯烃或炔烃的反应[κ 5 - Ñ，Ñ，Ñ，N，C - （ME 3 SiNCH 2 CH 2）2 NCH 2 CH 2 NSiMe 2 CH 2 ]锆（1）都大大下光解增强，提供了广泛的底物范围可行的催化加氢磷酸化。而二苯基膦已经热条件下无法访问的基板，烯烃底物的叔膦的完全转化在少在与环境温度下实现的四个小时1在紫外线照射下。以前的惰性烯烃现在是具有二苯膦的加氢磷酸化底物，以产生具有可调的空间和电子特性的叔膦配体。
• Catalytic Cleavage of Unactivated C(aryl)–P Bonds by Chromium
  作者：Jinghua Tang、Liang Ling、Shuqing Yuan、Meiming Luo、Xiaoming Zeng

  DOI：10.1021/acs.orglett.1c04325

  日期：2022.3.4

  We describe here the coupling to transform aryl phosphine derivatives by the cleavage of unactivated C(aryl)–P bonds with chromium catalysis, allowing us to achieve the reaction with alkyl bromides and arylmagnesium reagents under mild conditions. Mechanistic studies indicate that catalytic cleavage of unactivated C(aryl)–P bonds is due to the in situ formed reactive Cr, followed by transmetalation

  我们在这里描述了通过铬催化裂解未活化的 C(芳基)-P 键来转化芳基膦衍生物的偶联，使我们能够在温和的条件下实现与烷基溴和芳基镁试剂的反应。机理研究表明，未活化的 C(芳基)-P 键的催化裂解是由于原位形成的反应性 Cr，然后是金属转移和与烷基溴偶联。