(2-methyl-4-oxopent-2-yl)dipropylphosphineoxide | 1196795-10-4

• 分子结构分类: 有机化合物 - 有机磷化合物 - 有机膦及其衍生物
• 英文名称: (2-methyl-4-oxopent-2-yl)dipropylphosphineoxide
• 英文别名: 4-(Dipropylphosphoryl)-4-methylpentan-2-one；4-dipropylphosphoryl-4-methylpentan-2-one
• CAS: 1196795-10-4
• 化学式: C₁₂H₂₅O₂P
• 分子量: 232.303
• InChiKey: RQUTVHMMOVQAFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  (2-methyl-4-oxopent-2-yl)dipropylphosphineoxide 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以95%的产率得到(4-hydroxyimino-2-methylpent-2-yl)dipropylphosphine oxide
  参考文献：
  名称：

  Dimephosphone analogs: II. Dialkyl(diaryl)-(2-methyl-4-oxopent-2-yl)phosphine oxide oximes: Synthesis, structure, and generation of iminoxyl radicals

  摘要：

  Dialkyl(diaryl)-(2-methyl-4-oxopent-2-yl)phosphine oxide oximes have been synthesized for the first time. According to the X-ray diffraction data, these compounds in crystal exist as a single E isomer. Their structure in solution and the E/Z isomer ratio were determined by H-1 and C-13 NMR spectroscopy.

  DOI：

  10.1134/s107036321405020x
• 作为产物：
  描述：

  2-Chlor-3,3,5-trimethyl-1,2-oxaphosphol-4-en-2-oxid 、 magnesium 、 溴丙烷 在 sodium carbonate 作用下， 以 乙醚 、 水 为溶剂， 反应 0.5h， 以93%的产率得到(2-methyl-4-oxopent-2-yl)dipropylphosphineoxide
  参考文献：
  名称：

  2-chloro-3,3,5-trimethyl-2,3-dihydro-1,2λ5-oxaphosphole 2-oxide as precursor in a new synthesis of dialkyl(diaryl)-(2-methyl-4-oxopent-2-yl)phosphine oxides

  摘要：

  A new approach has been developed to the synthesis of dialkyl(diaryl)(2-methyl-4-oxopent-2-yl)-phosphine oxides that are structural analogs of the drug dimephosphon. This approach is based on the reaction of 2-chloro-3,3,5-trimethyl-3H-1,2 lambda(5)-oxaphosphole 2-oxide with Grignard compounds, and it ensures high yields of the target products. The structure of bis(2-methoxyphenyl)(2-methyl-4-oxopent-2-yl)phosphine oxide was determined by X-ray analysis. (2-Methyl-4-oxopent-2-yl)dipropylphosphine oxide with magnesium bromide formed a 4: 1 complex whose structure was also determined by X-ray analysis.

  DOI：

  10.1134/s1070428013040040

文献信息

• Synthesis of new 2-[2-(dialkyl(diaryl)-phosphoryl)-2-methylpropyl]quinoline-4-carboxylic acids
  作者：Dmitry A. Tatarinov、Viktoria I. Osipova、Andrei V. Bogdanov、Dmitry B. Krivolapov、Alexandra D. Voloshina、Vladimir F. Mironov

  DOI：10.1007/s10593-015-1761-y

  日期：2015.8

  A Pfitzinger reaction of isatin with 2-methyl-(4-oxopent-2-yl)dialkyl(diphenyl)phosphine oxides was used to synthesize new derivatives of 4-quinolinecarboxylic acids, containing a phosphine oxide fragment, and screening for antimicrobial activity was performed.

  靛红与2-甲基-（4-氧opent-2-基）二烷基（二苯基）膦氧化物的Pfitzinger反应用于合成含有膦氧化物片段的4-喹啉羧酸的新衍生物，并进行了抗菌活性的筛选。
• Dimephosphone analogs: a pharmacological aspect
  作者：V. F. Mironov、B. I. Buzykin、R. S. Garaev、D. A. Tatarinov、L. R. Kashapov、R. V. Chestnova、V. N. Nabiullin、A. V. Il´yasov、V. V. Zobova

  DOI：10.1007/s11172-014-0708-2

  日期：2014.9

  We studied some pharmacological properties of dimephosphone P—C and aza analogs, viz., dimethyl (2-methyl-4-oxopent-2-yl)phosphonate, which is one of the first organophosphorus drugs having no anticholinesterase activity. Replacement of two P—O—C fragments in dialkyl (2-methyl-4-oxopent-2-yl)phosphonates with the P—C ones on going to dialkyl-(2-methyl-4-oxopent-2-yl)phosphine oxides results in a dramatic

  我们研究了二甲磷酮 P-C 和氮杂类似物的一些药理特性，即（2-甲基-4-氧代戊-2-基）膦酸二甲酯，它是最早的没有抗胆碱酯酶活性的有机磷药物之一。将 (2-甲基-4-氧代戊-2-基)膦酸二烷基酯中的两个 P-O-C 片段替换为二烷基-(2-甲基-4-氧代戊-2-基)膦的 P-C 片段氧化物导致后者对温血动物的急性毒性显着降低。研究中的二甲基膦氮杂类似物和（γ-氧代烷基）氧化膦的毒性取决于引入的氮杂片段而不是氧原子的性质。发现二甲基膦吡啶基腙表现出高抗炎活性，这增加了人们对这类化合物作为有前途的抑结核剂的兴趣。
• 3-(4-Phosphoryl-4-methyl-2-oxopentyl)-3-hydroxyindolin-2-ones, the first phosphorus analogues of natural convolutamydines
  作者：Dmitry A. Tatarinov、Victoria I. Osipova、Andrei V. Bogdanov、Robert R. Fayzullin、Vladimir F. Mironov

  DOI：10.1016/j.mencom.2018.05.021

  日期：2018.5

  The first examples of phosphorus-containing analogues of natural alkaloids, convolutamydines, have been obtained by aldol condensation of 4-dialkyl(diphenyfiphosphoryl]-4-methylpentan-2-one with isatin. An unusually facile reversible process of dehydration-hydration of these phosphorus-containing hydroxy indoles has been discovered.
• Dimephosphone analogs: II. Dialkyl(diaryl)-(2-methyl-4-oxopent-2-yl)phosphine oxide oximes: Synthesis, structure, and generation of iminoxyl radicals
  作者：D. A. Tatarinov、V. F. Mironov、A. A. Kostin、E. V. Mironova、D. B. Krivolapov、V. I. Morozov、V. N. Nabiullin、A. V. Il’yasov、B. I. Buzykin

  DOI：10.1134/s107036321405020x

  日期：2014.5

  Dialkyl(diaryl)-(2-methyl-4-oxopent-2-yl)phosphine oxide oximes have been synthesized for the first time. According to the X-ray diffraction data, these compounds in crystal exist as a single E isomer. Their structure in solution and the E/Z isomer ratio were determined by H-1 and C-13 NMR spectroscopy.
• 2-chloro-3,3,5-trimethyl-2,3-dihydro-1,2λ5-oxaphosphole 2-oxide as precursor in a new synthesis of dialkyl(diaryl)-(2-methyl-4-oxopent-2-yl)phosphine oxides
  作者：D. A. Tatarinov、A. A. Kostin、T. A. Baronova、A. B. Dobrynin、E. V. Mironova、D. B. Krivolapov、B. I. Buzykin、V. F. Mironov

  DOI：10.1134/s1070428013040040

  日期：2013.4

  A new approach has been developed to the synthesis of dialkyl(diaryl)(2-methyl-4-oxopent-2-yl)-phosphine oxides that are structural analogs of the drug dimephosphon. This approach is based on the reaction of 2-chloro-3,3,5-trimethyl-3H-1,2 lambda(5)-oxaphosphole 2-oxide with Grignard compounds, and it ensures high yields of the target products. The structure of bis(2-methoxyphenyl)(2-methyl-4-oxopent-2-yl)phosphine oxide was determined by X-ray analysis. (2-Methyl-4-oxopent-2-yl)dipropylphosphine oxide with magnesium bromide formed a 4: 1 complex whose structure was also determined by X-ray analysis.