[2-(2-methyl-1,3-dioxolan-2-yl)phenyl]diphenylphosphine | 50778-03-5

• 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-(2-methyl-1,3-dioxolan-2-yl)phenyl]diphenylphosphine
• 英文别名: 2-(2-diphenylphosphinophenyl)-2-methyl-1,3-dioxolane；[2-(2-Methyl-1,3-dioxolan-2-yl)phenyl]-diphenylphosphane
• CAS: 50778-03-5
• 化学式: C₂₂H₂₁O₂P
• 分子量: 348.381
• InChiKey: IAEFMXYVOKQBEA-UHFFFAOYSA-N

物化性质

• 沸点：
  458.3±40.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [2-(2-methyl-1,3-dioxolan-2-yl)phenyl]diphenylphosphine 在 对甲苯磺酸 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 2.0h， 生成 [2-(3-pyrazolyl)phenyl]diphenylphosphine
  参考文献：
  名称：

  Novel phosphine ligands bearing 3(5)-pyrazolyl and 4-(2-amino)pyrimidinyl groups: Synthesis and coordination chemistry

  摘要：

  Novel triphenyl phosphine ligands bearing pyrazole or 2-aminopyrimidine groups in the ortho or meta position of one or three of the phenyl rings were obtained starting from the corresponding acyl derivatives Ph2P(o-C6H4-COCH3), Ph2P(m-C6H4-COCH3), Or P(m-C6H4-COCH3)(3)- Conversion of the acyl groups into 3-dimethylamino-2-propen-l-onyl units was achieved by reaction with HC(O-Me)(2)NMe2 which underwent ring closing with hydrazine or guanidine to yield the desired heterocycles. Two palladium complexes were synthesized using the coordinatively labile precursor (PhCN)(2)PdCl2, one of them could be characterized by X-ray structure analysis. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.08.032
• 作为产物：
  描述：

  2'-氟苯乙酮 在 氢化钾 、 对甲苯磺酸 作用下， 以 乙二醇二甲醚 为溶剂， 生成 [2-(2-methyl-1,3-dioxolan-2-yl)phenyl]diphenylphosphine
  参考文献：
  名称：

  Wasserlösliche Phosohane，十四。Hydrophile Derivate des Triphenylphosphans mit NH2-, COOH- 和 P(O)(OR)2-funktionalisierten Seitenketten / Water Soluble Phosphanes, XIV。具有 NH2、COOH 和 P(O)(OR)2 官能化侧链的三苯基膦的亲水衍生物

  摘要：

  使用 KOtBu 作为碱，邻氟苯乙酸或邻氟苄胺与 PhPH2 的亲核膦酰化得到具有末端 CH2-COOH 和 CH2-NH2 取代基的亲水性叔膦 3 和 4a。相应的二级膦配体2或5可以通过Pd催化的邻碘苯乙酸与PhPH2的PC偶联或邻氟苯乙酸的选择性亲核膦酰化获得。使用邻碘苄基氯或间碘苄基溴作为起始材料，在两步合成中获得了三苯基膦的新型膦酰甲基衍生物 7a、7b。Arbusov 与 P(OEt)3 的反应和 Pd 催化的 PC 与 Ph2PH 的偶联反应得到酯 7a、7b。7a 的纯化是通过其 BH3 加合物 8a 实现的。脱保护，用NaOH水解和中和得到水溶性钠盐9a、9b。通过添加 (MeO)2P(O)H 或 Me2P，可以直接获得邻二苯基膦苄基膦酸酯（例如 7a）的 α-羟基和 α-苄氨基衍生物 12 和 14 以及相应的 Me2P(O) 类似物 13 和 16 (O)H 分别为邻位膦基苯甲醛

  DOI：

  10.1515/znb-1999-1210
• 作为试剂：
  描述：

  2-溴联苯 、 5-氯-2-甲氧基苯胺 在 [2-(2-methyl-1,3-dioxolan-2-yl)phenyl]diphenylphosphine 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 Biphenyl-2-yl-(5-chloro-2-methoxy-phenyl)-amine
  参考文献：
  名称：

  A Fully Integrated High-Throughput Screening Methodology for the Discovery of New Polyolefin Catalysts:  Discovery of a New Class of High Temperature Single-Site Group (IV) Copolymerization Catalysts

  摘要：

  For the first time, new catalysts for olefin polymerization have been discovered through the application of fully integrated high-throughput primary and secondary screening techniques supported by rapid polymer characterization methods. Microscale 1-octene primary screening polymerization experiments combining arrays of ligands with reactive metal complexes M(CH2Ph)(4) (M = Zr, Hf) and multiple activation conditions represent a new high-throughput technique for discovering novel group (IV) polymerization catalysts. The primary screening methods described here have been validated using a commercially relevant polyolefin catalyst, and implemented rapidly to discover the new amide-ether based hafnium catalyst [eta(2)-(N,O)-(2-MeO-C6H4)(2,4,6-Me3C6H2)N]Hf(CH2Ph)(3) (1), which is capable of polymerizing 1-octene to high conversion. The molecular structure of I has been determined by X-ray diffraction. Larger scale secondary screening experiments performed on a focused 96-member amine-ether library demonstrated the versatile high temperature ethylene-1-octene copolymerization capabilities of this catalyst class, and led to significant performance improvements over the initial primary screening discovery. Conventional one gallon batch reactor copolymerizations performed using selected amide-ether hafnium compounds confirmed the performance features of this new catalyst class, serving to fully validate the experimental results from the high-throughput approaches described herein.

  DOI：

  10.1021/ja020868k

文献信息

• Phenyl Backbone-Derived P,O- and P,N-Ligands for Palladium/Ligand-Catalyzed Aminations of Aryl Bromides, Iodides, and Chlorides. Syntheses and Structures of (P,O)<i>_n</i>-Palladium(II)Aryl(Br) Complexes
  作者：Xiaohong Bei、Tetsuo Uno、Jeff Norris、Howard W. Turner、W. Henry Weinberg、Anil S. Guram、Jeffrey L. Petersen

  DOI：10.1021/om9900162

  日期：1999.5.1

  palladium/ligand-catalyzed aryl aminations. The P,O-ligands 2-(2‘-diphenylphosphinophenyl)-2-methyl-1,3-dioxolane (1) and 2-(2‘-dicyclohexylphosphinophenyl)-2-methyl-1,3-dioxolane (6) in combination with Pd(dba)2afford active catalysts for general aminations of aryl bromides, iodides, and chlorides. The Pd/ligand 6 catalyst, in particular, is efficient for general aminations of aryl chlorides. But the structurally

  苯基骨架衍生的P，O-和P，N的化合物1 - 10进行了调查它们的效用，如钯/配体催化的芳基胺化的配体。P，O-配体2-（2'-二苯基膦基苯基）-2-甲基-1,3-二氧戊环（1）和2-（2'-二环己基膦基苯基）-2-甲基-1,3-二氧戊环（6）与Pd（dba）2的结合提供了用于芳基溴化物，碘化物和氯化物的一般胺化的活性催化剂。特别是，Pd /配体6催化剂对于芳基氯化物的一般胺化是有效的。但是与结构相关的配体2-（2'-二苯基膦基苯基）-1,3-二氧戊环（2）和其他P，O-或P，N-配体效果较差。Pd（dba）的反应2，多余的4-吨卜-C 6 H ^ 4 Br和过量配体（1，6，2）或PD [P（配体置换反应ö -toluyl）3 ]（4-吨卜-C 6 H ^ 4）（μ-溴）} 2与配体1，6，和2得到的Pd的电位催化中间体/ L催化（L = 1，6，2）芳基胺化，即，LPD（ 4吨Bu-C
• Novel phosphine ligands bearing 3(5)-pyrazolyl and 4-(2-amino)pyrimidinyl groups: Synthesis and coordination chemistry
  作者：Yu Sun、Antje Hienzsch、Jens Grasser、Eberhardt Herdtweck、Werner R. Thiel

  DOI：10.1016/j.jorganchem.2005.08.032

  日期：2006.1

  Novel triphenyl phosphine ligands bearing pyrazole or 2-aminopyrimidine groups in the ortho or meta position of one or three of the phenyl rings were obtained starting from the corresponding acyl derivatives Ph2P(o-C6H4-COCH3), Ph2P(m-C6H4-COCH3), Or P(m-C6H4-COCH3)(3)- Conversion of the acyl groups into 3-dimethylamino-2-propen-l-onyl units was achieved by reaction with HC(O-Me)(2)NMe2 which underwent ring closing with hydrazine or guanidine to yield the desired heterocycles. Two palladium complexes were synthesized using the coordinatively labile precursor (PhCN)(2)PdCl2, one of them could be characterized by X-ray structure analysis. (c) 2005 Elsevier B.V. All rights reserved.
• Wasserlösliche Phosohane, XIV. Hydrophile Derivate des Triphenylphosphans mit NH_2-, COOH- und P(O)(OR)₂-funktionalisierten Seitenketten / Water Soluble Phosphanes, XIV. Hydrophilic Derivatives of Triphenylphosphane with NH₂, COOH and P (O)(OR)₂ Functionalized Side Chains
  作者：Christian Liek、Peter Machnitzki、Thomas Nickel、Stefan Schenk、Michael Tepper、Othmar Stelzer

  DOI：10.1515/znb-1999-1210

  日期：1999.12.1

  Nucleophilic phosphanylation of ortho-fluorophenylacetic acid or ortho-fluorobenzylamine with PhPH2 using KOtBu as the base affords the hydrophilic tertiary phosphanes 3 and 4a with terminal CH2-COOH and CH2-NH2 substituents. The corresponding secondary phosphane ligands 2 or 5 may be obtained by Pd-catalyzed P-C coupling of ortho-iodophenylacetic acid with PhPH2 or selective nucleophilic phosphanylation

  使用 KOtBu 作为碱，邻氟苯乙酸或邻氟苄胺与 PhPH2 的亲核膦酰化得到具有末端 CH2-COOH 和 CH2-NH2 取代基的亲水性叔膦 3 和 4a。相应的二级膦配体2或5可以通过Pd催化的邻碘苯乙酸与PhPH2的PC偶联或邻氟苯乙酸的选择性亲核膦酰化获得。使用邻碘苄基氯或间碘苄基溴作为起始材料，在两步合成中获得了三苯基膦的新型膦酰甲基衍生物 7a、7b。Arbusov 与 P(OEt)3 的反应和 Pd 催化的 PC 与 Ph2PH 的偶联反应得到酯 7a、7b。7a 的纯化是通过其 BH3 加合物 8a 实现的。脱保护，用NaOH水解和中和得到水溶性钠盐9a、9b。通过添加 (MeO)2P(O)H 或 Me2P，可以直接获得邻二苯基膦苄基膦酸酯（例如 7a）的 α-羟基和 α-苄氨基衍生物 12 和 14 以及相应的 Me2P(O) 类似物 13 和 16 (O)H 分别为邻位膦基苯甲醛