二甲基磷酰肼 | 58816-61-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 中文名称: 二甲基磷酰肼
• 英文名称: phosphorohydrazidic acid dimethyl ester
• 英文别名: Hydrazidophosphorsaeuredimethylester；dimethyl phosphorohydrazidate；Dimethoxyphosphorylhydrazine
• CAS: 58816-61-8
• 化学式: C₂H₉N₂O₃P
• 分子量: 140.079
• InChiKey: KGXMHRJJBBOWIZ-UHFFFAOYSA-N

物化性质

• 熔点：
  140-141 °C
• 沸点：
  174.5±23.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  73.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二甲基磷酰肼 、 2-苯基-1-丙烯 在 铁酞菁 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 以83%的产率得到dimethyl (2-hydroxy-2-phenyl)propylphosphonate
  参考文献：
  名称：

  Synthesis of β-hydroxyphosphonates by iron-catalyzed oxidative addition of phosphonyl radicals to alkenes

  摘要：

  Phosphorohydrazidates have been shown to work as radical precursors by iron-catalyzed aerobic oxidation to generate corresponding phosphonyl radicals. Generated radicals cause intermolecular addition to various alkenes in the presence of molecular oxygen to give beta-hydroxyphosphonate compounds in good yield. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.026
• 作为产物：
  描述：

  1-dimethoxyphosphoryl-5-phenyl-1H-pyrazole-3-carboxylic acid methyl ester 在 一水合肼 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 二甲基磷酰肼
  参考文献：
  名称：

  Felcht,U.; Regitz,M., Justus Liebigs Annalen der Chemie, 1977, p. 1309 - 1320

  摘要：

  DOI：

文献信息

• Copper-catalyzed aerobic cascade cycloamination and acyloxylation: a direct approach to 4-acyloxy-1H-pyrazoles
  作者：Zhengwei Ding、Qitao Tan、Mingchun Gao、Bin Xu

  DOI：10.1039/c5ob00409h

  日期：——

  An efficient copper-catalyzed regioselective olefinic C(sp²)–H bond cycloamination and acyloxylation was developed to give acyloxylated pyrazoles under mild conditions, which combines the formation of the pyrazole skeleton and installation of an acyloxyl group in a single step.

  一种高效的铜催化的选择性合成烯烃C(sp2)-H键环胺化和酰氧化反应被开发出来，在温和条件下得到了酰氧化吡唑化合物，该方法将吡唑骨架的形成和酰氧基团的引入结合在一个步骤中。
• Phosphoramidates as Transient Precursors of Nitrogen‐Centered Radical Under Visible‐Light Irradiation: Application to the Synthesis of Phthalazine Derivatives
  作者：Maxime De Abreu、Mohamed Selkti、Philippe Belmont、Etienne Brachet

  DOI：10.1002/adsc.202000018

  日期：2020.5.26

  N‐Centered Radical (NCR) precursors under visible‐light irradiation. More precisely among this class of phosphorus‐derived compounds, we studied the radical reactivity of phosphonohydrazones, under mild reaction conditions, which allowed the synthesis of a wide and diversified library of the scarcely reported phthalazine scaffold. Mechanistic investigations confirmed the formation of a NCR from these brand‐new

  磷酰胺盐首次在可见光照射下作为有效的N中心自由基（NCR）前体出现。更确切地说，在这类磷衍生化合物中，我们研究了膦酰hydr在温和的反应条件下的自由基反应性，从而可以合成一个鲜为人知的邻苯二甲酰胺骨架的宽泛且多样化的文库。机理研究证实，这些全新的膦酰hydr （衍生自氨基磷酸酯）形成了NCR，它们进一步参与了分子内6- exo- dig环化反应以提供酞嗪。与其他预活化部分相比，氨基磷酸酯基团是自消灭的，因此增强了其对C-N键形成的吸引力。
• An efficient synthesis of O,O- Di Propyl (E)-2-[1-methyl 2-oxopropylidene]phosphorohydrazidothiolate (E) Oxime and Its Analogues: A Potential Marine Toxin
  作者：Arvind K. Gupta、D. K. Dubey、B. D. Parashar、M. P. Kaushik

  DOI：10.1080/10426500701796249

  日期：2008.7.4

  An efficient method for the synthesis of Ptychodiscus brevis toxin O,O- di n-propyl (E)-2-[1-methyl 2-oxopropylidene]phosphorohydrazidothiolate (E) oxime (TG-1) and its analogues has been developed using thermally stable and recyclable silica gel and Na2SO4 as a condensing agent and water scavenger, respectively. The compounds were evaluated against fish Rasbora daniconius by determining the LC50 and LC90 values. The results of biological evaluation showed that these compounds have high degree of toxicity.
• Felcht,U.; Regitz,M., Justus Liebigs Annalen der Chemie, 1977, p. 1309 - 1320
  作者：Felcht,U.、Regitz,M.

  DOI：——

  日期：——
• Synthesis of β-hydroxyphosphonates by iron-catalyzed oxidative addition of phosphonyl radicals to alkenes
  作者：Tsuyoshi Taniguchi、Atsushi Idota、Shin’ichi Yokoyama、Hiroyuki Ishibashi

  DOI：10.1016/j.tetlet.2011.07.026

  日期：2011.9

  Phosphorohydrazidates have been shown to work as radical precursors by iron-catalyzed aerobic oxidation to generate corresponding phosphonyl radicals. Generated radicals cause intermolecular addition to various alkenes in the presence of molecular oxygen to give beta-hydroxyphosphonate compounds in good yield. (C) 2011 Elsevier Ltd. All rights reserved.