α,α''-di(phenylhydrophosphoxyl)-meta-xylene | 1246895-34-0

• 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: α,α''-di(phenylhydrophosphoxyl)-meta-xylene
• 英文别名: 1,3-Bis(phenylphosphonoylmethyl)benzene；1,3-bis(phenylphosphonoylmethyl)benzene
• CAS: 1246895-34-0
• 化学式: C₂₀H₂₀O₂P₂
• 分子量: 354.325
• InChiKey: YVSXVVWZECEHLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  碘苯 、 α,α''-di(phenylhydrophosphoxyl)-meta-xylene 在 tris-(dibenzylideneacetone)dipalladium(0) 、 4,5-bis(diphenylphosphino)-9,9-dimethylxanthen 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.17h， 以77%的产率得到(1,3-phenylenebis(methylene))bis(diphenylphosphine oxide)
  参考文献：
  名称：

  室温下，仲膦氧化物的钯介导的P-芳构化

  摘要：

  我们表明，使用1摩尔％的由三（二亚苄基丙酮）二钯和Xantphos（1）原位形成的催化剂，可以广泛地将芳基碘与仲膦氧化物有效偶联。鳞状的（S）-甲基苯基膦氧化物[ （S）-2e ]显示发生芳基化而没有可检测到的立体侵蚀。证明了该方法在合成新的P-手性膦和PCP配体中的应用。

  DOI：

  10.1021/ol301831k
• 作为产物：
  描述：

  间苯二甲醛 、 苯基膦 在 三氟乙酸 作用下， 以72%的产率得到α,α''-di(phenylhydrophosphoxyl)-meta-xylene
  参考文献：
  名称：

  Single-Step Synthesis of Secondary Phosphine Oxides

  摘要：

  We report that in the presence of trifluoroacetic acid primary phosphines undergo efficient addition to aldehydes to form the corresponding secondary phosphine oxides in 47-97% yield. This transformation is compatible with aryl and alkyl phosphines, as well as a broad range of aldehydes, including formaldehyde. By using 1,5-dialdehydes as reaction partners, the addition provides a straightforward route to bis(phosphine oxides), which are difficult to prepare by alternative methods. In the presence of boron trifluoride diethyl etherate as reagent, benzophenone was shown to couple to phenylphosphine and cyclohexylphosphine in 92% and 72% yield, respectively. Twenty-three examples are presented.

  DOI：

  10.1021/om100571w

文献信息

• Room Temperature, Palladium-Mediated <i>P</i>–Arylation of Secondary Phosphine Oxides
  作者：Aaron J. Bloomfield、Seth B. Herzon

  DOI：10.1021/ol301831k

  日期：2012.9.7

  iodides are efficiently coupled with secondary phosphine oxides using 1 mol % of a catalyst formed in situ from tris(dibenzylideneacetone)dipalladium and Xantphos (1). Scalemic (S)-methylphenylphosphine oxide [(S)-2e] is shown to undergo arylation without detectable stereoerosion. The application of this method to the synthesis of novel P-chiral phosphines and PCP ligands is demonstrated.

  我们表明，使用1摩尔％的由三（二亚苄基丙酮）二钯和Xantphos（1）原位形成的催化剂，可以广泛地将芳基碘与仲膦氧化物有效偶联。鳞状的（S）-甲基苯基膦氧化物[ （S）-2e ]显示发生芳基化而没有可检测到的立体侵蚀。证明了该方法在合成新的P-手性膦和PCP配体中的应用。
• Single-Step Synthesis of Secondary Phosphine Oxides
  作者：Aaron J. Bloomfield、Jack M. Qian、Seth B. Herzon

  DOI：10.1021/om100571w

  日期：2010.9.27

  We report that in the presence of trifluoroacetic acid primary phosphines undergo efficient addition to aldehydes to form the corresponding secondary phosphine oxides in 47-97% yield. This transformation is compatible with aryl and alkyl phosphines, as well as a broad range of aldehydes, including formaldehyde. By using 1,5-dialdehydes as reaction partners, the addition provides a straightforward route to bis(phosphine oxides), which are difficult to prepare by alternative methods. In the presence of boron trifluoride diethyl etherate as reagent, benzophenone was shown to couple to phenylphosphine and cyclohexylphosphine in 92% and 72% yield, respectively. Twenty-three examples are presented.