(3-nitrophenyl)diphenylphosphine oxide | 31638-87-6

• 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: (3-nitrophenyl)diphenylphosphine oxide
• 英文别名: 3-nitrophenyldiphenylphosphine oxide；Diphenyl-<3-nitro-phenyl>-phosphinoxid；Diphenyl-(3-nitro-phenyl)-phosphinoxid；1-Diphenylphosphoryl-3-nitrobenzene
• CAS: 31638-87-6
• 化学式: C₁₈H₁₄NO₃P
• 分子量: 323.288
• InChiKey: QJNSCTNRQJTSHB-UHFFFAOYSA-N

物化性质

• 熔点：
  91 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  527.1±42.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3-nitrophenyl)diphenylphosphine oxide 在 palladium on activated charcoal 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.5h， 以87%的产率得到(3-aminophenyl)diphenylphosphine oxide
  参考文献：
  名称：

  Triphenylphosphine oxide supported on non-cross-linked maleimide–styrene copolymer: application as a novel Hendrickson reagent

  摘要：

  A new triphenylphosphine oxide reagent linked to a linear maleimide-styrene copolymer is synthesized. This phosphine-bound copolymer is converted to copolymer-supported triphenylphosphine ditriflate as a novel Hendrickson reagent by treatment with triflic anhydride. This reacts rapidly in various dehydration reactions such as anhydride, ester and amide formation. This linear and soluble support is also easily recovered and recycled several times without loss of efficiency. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.001
• 作为产物：
  描述：

  三苯基氧化膦 在 硫酸 、 potassium nitrate 作用下， 反应 3.0h， 生成 (3-nitrophenyl)diphenylphosphine oxide
  参考文献：
  名称：

  （杂）芳族间隔基对含硫酮硫供体的对位钳位配体中环palpalpalation方向的影响

  摘要：

  3-二苯基硫代磷酰基苯胺和间苯二甲酸或2,6-吡啶二羧酸被用作合成带有硫代酰胺和硫代磷酰基供体基团的二位钳位配体的关键前体。取决于（杂）芳族间隔物的性质（间-官能化的亚苯基或吡啶环），所述配体衍生的后行协调或者在横向或中央钳单元，选择性地得到双核（在基于亚苯基-配体的情况下）或单核（在基于吡啶的衍生物的情况下）Pd（II）钳形配合物。基于单核吡啶的巴拉达环易发生仲硫酰胺基的去质子化，从而导致硫化物簇。通过单晶XRD阐明获得的四聚体的结构。

  DOI：

  10.1016/j.jorganchem.2019.02.014

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.
• PAVLOV G. P.; KUXTIN V. A.; GOLYNINA N. A.; KORMACHEV V. V., ZH. OBSHCH. XIMII, 1980, 50, HO 8, 1902-1903
  作者：PAVLOV G. P.、 KUXTIN V. A.、 GOLYNINA N. A.、 KORMACHEV V. V.

  DOI：——

  日期：——
• Triphenylphosphine oxide supported on non-cross-linked maleimide–styrene copolymer: application as a novel Hendrickson reagent
  作者：Hossein Mahdavi、Javad Amani

  DOI：10.1016/j.tetlet.2008.02.001

  日期：2008.3

  A new triphenylphosphine oxide reagent linked to a linear maleimide-styrene copolymer is synthesized. This phosphine-bound copolymer is converted to copolymer-supported triphenylphosphine ditriflate as a novel Hendrickson reagent by treatment with triflic anhydride. This reacts rapidly in various dehydration reactions such as anhydride, ester and amide formation. This linear and soluble support is also easily recovered and recycled several times without loss of efficiency. (C) 2008 Elsevier Ltd. All rights reserved.
• Effect of a (hetero)aromatic spacer on the direction of cyclopalladation in ditopic pincer ligands with thione sulfur donors
  作者：Diana V. Aleksanyan、Svetlana G. Churusova、Zinaida S. Klemenkova、Yulia V. Nelyubina、Alexander S. Peregudov、Vladimir A. Kozlov

  DOI：10.1016/j.jorganchem.2019.02.014

  日期：2019.4

  ditopic pincer ligands bearing thioamide and thiophosphoryl donor groups. Depending on the nature of a (hetero)aromatic spacer (meta-functionalized phenylene or pyridine rings), the ligands derived underwent coordination either at the lateral or central pincer units, selectively affording binuclear (in the case of phenylene-based ligand) or mononuclear (in the case of pyridine-based derivative) Pd(II)

  3-二苯基硫代磷酰基苯胺和间苯二甲酸或2,6-吡啶二羧酸被用作合成带有硫代酰胺和硫代磷酰基供体基团的二位钳位配体的关键前体。取决于（杂）芳族间隔物的性质（间-官能化的亚苯基或吡啶环），所述配体衍生的后行协调或者在横向或中央钳单元，选择性地得到双核（在基于亚苯基-配体的情况下）或单核（在基于吡啶的衍生物的情况下）Pd（II）钳形配合物。基于单核吡啶的巴拉达环易发生仲硫酰胺基的去质子化，从而导致硫化物簇。通过单晶XRD阐明获得的四聚体的结构。