bis(benzo[d][1,3]dioxol-5-yl)(phenyl)phosphine oxide | 1448632-03-8

• 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: bis(benzo[d][1,3]dioxol-5-yl)(phenyl)phosphine oxide
• 英文别名: 5-[1,3-Benzodioxol-5-yl(phenyl)phosphoryl]-1,3-benzodioxole；5-[1,3-benzodioxol-5-yl(phenyl)phosphoryl]-1,3-benzodioxole
• CAS: 1448632-03-8
• 化学式: C₂₀H₁₅O₅P
• 分子量: 366.31
• InChiKey: CZKXBINISACFMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  bis(1,3-benzodioxol-5-yl)phosphine oxide 、 二苯基碘三氟甲烷磺酸盐 在 三乙胺 、 copper(l) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以94%的产率得到bis(benzo[d][1,3]dioxol-5-yl)(phenyl)phosphine oxide
  参考文献：
  名称：

  Copper-Catalyzed P-Arylation via Direct Coupling of Diaryliodonium Salts with Phosphorus Nucleophiles at Room Temperature

  摘要：

  A new method for copper-catalyzed P-C bond formation through reaction of phosphorus nucleophiles with diaryliodonium salts at room temperature is described. Most target products are obtained with this method in high yields within a short reaction time of 10 min. It can be easily adapted to large-scale preparations. When unsymmetrical iodonium salts are employed, nucleophilic substitution occurs preferentially on the sterically hindered aromatic ring or the more electron-deficient ring.

  DOI：

  10.1021/jo4012199

文献信息

• Palladium-catalyzed air-based oxidative coupling of arylboronic acids with H-phosphine oxides leading to aryl phosphine oxides
  作者：Tingting Fu、Hongwei Qiao、Zhimin Peng、Gaobo Hu、Xueji Wu、Yuxing Gao、Yufen Zhao

  DOI：10.1039/c3ob42470g

  日期：——

  We present a novel and highly efficient methodology that allows for the construction of C–P bonds via the palladium-catalyzed air-based oxidative coupling of various commercially available arylboronic acids with easily oxidized H-phosphine oxides leading to valuable aryl phosphine oxides, particularly triarylphosphine oxides, with the use of air as the green oxidant, broad substrate applicability and

  我们提出了一种新颖而高效的方法，该方法允许通过各种商品化的芳基硼酸与易氧化的H-膦氧化物的钯催化的基于空气的氧化偶联来构建C-P键，从而产生有价值的芳基膦氧化物，特别是三芳基膦使用空气作为绿色氧化剂的氧化物，具有广泛的底材适用性，并具有良好的优异收率。所描述的催化系统应该是对Chan-Lam型反应的有效补充，并在合成程序中有用。
• Copper-Catalyzed P-Arylation via Direct Coupling of Diaryliodonium Salts with Phosphorus Nucleophiles at Room Temperature
  作者：Jian Xu、Pengbo Zhang、Yuzhen Gao、Yiyin Chen、Guo Tang、Yufen Zhao

  DOI：10.1021/jo4012199

  日期：2013.8.16

  A new method for copper-catalyzed P-C bond formation through reaction of phosphorus nucleophiles with diaryliodonium salts at room temperature is described. Most target products are obtained with this method in high yields within a short reaction time of 10 min. It can be easily adapted to large-scale preparations. When unsymmetrical iodonium salts are employed, nucleophilic substitution occurs preferentially on the sterically hindered aromatic ring or the more electron-deficient ring.