五甲基磷酰胺 | 10159-46-3

• 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: 五甲基磷酰胺
• 英文名称: Pentamethylphosphoramide
• 英文别名: pentamethyl-phosphamide；Phosphorsaeure-bis-dimethylamid-methylamid；Pentamethyl-phosphamid；(Dimethylaminophosphinyl)methylamin；Pentamethyl-phosphorsaeuretriamid；Pentamethylphosphorsaeuretriamid；N-[bis(dimethylamino)phosphoryl]methanamine
• CAS: 10159-46-3
• 化学式: C₅H₁₆N₃OP
• mdl: MFCD01705441
• 分子量: 165.175
• InChiKey: JSJBYUNWLNWERF-UHFFFAOYSA-N

物化性质

• 沸点：
  137-143 °C(Press: 3 Torr)
• 密度：
  1.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  10
• 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：
  35.6
• 氢给体数：
  1
• 氢受体数：
  4

ADMET

代谢

五甲基磷酰胺是六甲基磷酰胺的人类已知代谢物。

Pentamethylphosphoramide is a known human metabolite of hexamethylphosphoramide.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  五甲基磷酰胺 在 copper(I) chloride 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 2.08h， 生成 N,N,N',N',N''-Pentamethyl-N''-[4-(pyrrolidin-1-yl)but-2-yn-1-yl]phosphoric triamide
  参考文献：
  名称：

  Corbel, Bernard; Paugam, Jean-Paul; Sturtz, Georges, Canadian Journal of Chemistry, 1980, vol. 58, # 20, p. 2183 - 2188

  摘要：

  DOI：
• 作为产物：
  描述：

  六甲基磷酰三胺 在 potassium permanganate 作用下， 生成 五甲基磷酰胺
  参考文献：
  名称：

  昆虫化学杀菌剂。VI。六甲基磷酸三酰胺的氧化和N-甲酰基磷酸酰胺的合成。

  摘要：

  DOI：

  10.1021/jm00311a602

文献信息

• Thermal Oxidative Deamination of Aliphatic Amines to Aldehydes with Bis(diphenylphosphinyl) Peroxide
  作者：Guy Masse、Georges Sturtz

  DOI：10.1055/s-1988-27750

  日期：——

  Reaction of N-substituted alkylamines having pseudoacidic hydrogen at the 1-methylene group with bis(diphenylphosphinyl) peroxide yields the deaminated products by thermal elimination of diphenylphosphinic acid from the intermediate O-diphenylphosphinylhydroxylamines.

  将在 1-亚甲基上具有假酸性氢的 N-取代烷基胺与过氧化双（二苯基膦）反应，通过热消除中间 O-二苯基膦羟基胺中的二苯基膦酸，得到脱氨基产物。
• Phase-transfer Reactions Catalyzed by Phosphoric Triamides Containing Hydrophobic Groups
  作者：Masao Tomoi、Takashi Hasegawa、Manabu Ikeda、Hiroshi Kakiuchi

  DOI：10.1246/bcsj.52.1653

  日期：1979.6

  Aqueous organic two-phase reactions (halogen exchange, cyanation, and borohydride reduction) have been catalyzed by phosphoric triamides containing hydrophobic groups. The phosphoric triamides, which have a high cation binding ability, exibited high catalytic activity for the two-phase reactions. The catalytic activity of N-alkylteramethylphosphoric triamides (1) was higher than that of the corresponding pentamethyl derivatives and the difference has been explained in terms of the contribution of the dimeric species of 1 and/or hydrogen bonding between the NH of 1 and the anionic moieties of inorganic reagents.

  含疏水基团的磷酸三酰胺催化了水有机两相反应（卤素交换、氰化和硼氢化还原）。磷酸三酰胺具有很强的阳离子结合能力，在两相反应中表现出很高的催化活性。N- 烷基三甲基磷酸三酰胺（1）的催化活性高于相应的五甲基衍生物，这种差异可以用 1 的二聚物和/或 1 的 NH 与无机试剂阴离子之间的氢键作用来解释。
• Dimethylamino-derivatives of bis(dichlorophosphinyl)methylamine, [Cl2P(:O)]2NMe
  作者：I. Irvine、R. Keat

  DOI：10.1039/dt9720000017

  日期：——

  The reactions of bis(dichlorophosphinyl)methylamine, [Cl2P(:O)]2NMe, with dimethylamine and with NN-dimethyl(trimethylsilyl)amine have been studied. Mono, non-geminal bis-, tris-, and tetrakis-dimethylaminoderivatives have been identified; the bis-derivative has been separated into diastereomeric forms which interconverted either when heated, or in the presence of tetraethylammonium chloride. The mono-derivative

  研究了双（二氯膦基）甲胺，[Cl 2 P（：O）] 2 NMe，二甲胺和NN-二甲基（三甲基甲硅烷基）胺的反应。已经鉴定了单，非双链的双，三和四甲基二甲基氨基衍生物；该双衍生物已被分离成非对映体形式，该非对映体形式在加热时或在氯化四乙铵存在下可相互转化。单价衍生物也可从磷酰卤与七甲基二硅氮烷，（Me 3 Si）2 NMe的反应中获得，而双晶双-和三价衍生物是从（Me 2 N）2 P（： O）·NHMe与磷酰氯和Cl2 P（：O）·NMe 2。通过1 H和31 P nmr光谱确定了结构，并将结果与​​六氯环三磷氮杂三烯N 3 P 3 Cl 6的二甲基氨基分解获得的结果进行了比较。
• Benmaarouf-Khallaayoun, Z.; Baboulene, M.; Speziale, V., Synthetic Communications, 1985, vol. 15, # 3, p. 233 - 242
  作者：Benmaarouf-Khallaayoun, Z.、Baboulene, M.、Speziale, V.、Lattes, A.

  DOI：——

  日期：——
• Lithiated anions derived from (alkenyl)pentamethyl phosphoric triamides: Useful synthons for the stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of queen substance and royal jelly of honeybee Apis mellifera
  作者：Tomasz K. Olszewski、Catherine Bomont、Philippe Coutrot、Claude Grison

  DOI：10.1016/j.jorganchem.2010.06.020

  日期：2010.10

  Lithiated anions derived from (alkenyl) pentamethyl phosphoric triamides as homoenolate equivalents are used in the reaction with halogenated acetal and ketal giving regioselectively the gamma-alkylation adducts. Chemoselective acidic hydrolysis of the enephosphoramide moiety in the presence of acetal or ketal groups leads to expected carbonyl products, key intermediates in the synthesis of natural compounds. The synthetic potential of the presented strategy is illustrated by stereoselective synthesis of two pheromones namely, 9-oxo-2(E)-decenoic acid 1 from queen substance and 10-hydroxy-2(E)-decenoic acid 2 from royal jelly of honeybee Apis mellifera. (C) 2010 Elsevier B.V. All rights reserved.

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