N-allyl-N-methyl-(bisdimethylamino) phosphoramide | 57041-73-3

• 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
• 英文名称: N-allyl-N-methyl-(bisdimethylamino) phosphoramide
• 英文别名: Phosphoric triamide, pentamethyl-2-propenyl-；N-[bis(dimethylamino)phosphoryl]-N-methylprop-2-en-1-amine
• CAS: 57041-73-3
• 化学式: C₈H₂₀N₃OP
• 分子量: 205.24
• InChiKey: GXCSCLQPRKVSNS-UHFFFAOYSA-N

物化性质

• 沸点：
  105 °C(Press: 4 Torr)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-allyl-N-methyl-(bisdimethylamino) phosphoramide 在 oxonium 作用下， 以56%的产率得到N-甲基烯丙基胺
  参考文献：
  名称：

  Thermal Oxidative Deamination of Aliphatic Amines to Aldehydes with Bis(diphenylphosphinyl) Peroxide

  摘要：

  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。

  DOI：

  10.1055/s-1988-27750
• 作为产物：
  描述：

  五甲基磷酰胺 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到N-allyl-N-methyl-(bisdimethylamino) phosphoramide
  参考文献：
  名称：

  Thermal Oxidative Deamination of Aliphatic Amines to Aldehydes with Bis(diphenylphosphinyl) Peroxide

  摘要：

  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。

  DOI：

  10.1055/s-1988-27750

文献信息

• A concise synthesis of sex pheromone of mediterranean fruit fly,<i>Ceratitis capitata</i>via lithiated carbanion derived from enephosphoramide
  作者：Tomasz Krzysztof Olszewski、Claude Grison

  DOI：10.1002/hc.20588

  日期：——

  A novel and versatile synthetic approach to the preparation of (E)-non-6-en-1-ol, a sex pheromone of the Mediterranean fruit fly, Ceratitis capitata, is presented. This pheromone can be viewed as potential active component for lures designed to control and eradication of Mediterranean fruit fly. The described protocol is a six-step reaction sequence producing the desired compound with 28% overall yield

  提出了一种新的、通用的合成方法来制备 (E)-non-6-en-1-ol，一种地中海果蝇的性信息素，Ceratitis capitalata。该信息素可被视为用于控制和根除地中海果蝇的诱饵的潜在活性成分。所描述的协议是一个六步反应序列, 以 28% 的总产率从市售和廉价的起始材料和最终结构中存在的双键的总 E 立体选择性中产生所需的化合物。所提出策略成功的关键是锂化 α-烯丙基磷酰胺碳负离子的应用及其与卤代缩醛的反应。© 2010 Wiley Periodicals, Inc. 21:139–147, 2010；在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20588
• Equivalents anioniques homoenolates issus d'enephosphoramides: reaction avec la benzophenone
  作者：Ph. Coutrot、J.R. Dormoy、A. Moukimou

  DOI：10.1016/s0022-328x(00)99263-5

  日期：1983.11

  α-Phosphoramidolithium substituted allylic carbanions are used as homoenolate reagents with benzophenone and give regioselectively α- or γ-hydroxyalkylation products. Replacement of lithium by magnesium leads to γ substitution almost exclusively. Acidic hydrolysis of the adducts is a novel route to γ-lactol.

  α-磷酰胺基锂取代的烯丙基碳负离子与二苯甲酮一起用作均烯酸酯试剂，可选择性地产生α-或γ-羟烷基化产物。用镁取代锂几乎完全导致γ取代。加合物的酸性水解是制备γ-乳糖醇的新途径。
• Hydroboration d'amines insaturees
  作者：Zahra Benmaarouf-Khallaayoun、Michel Baboulene、Vincent Speziale、Armand Lattes

  DOI：10.1016/0022-328x(85)87408-8

  日期：1985.7

  The amino group of N-allylic amines which is protected by a phosphorylated grouping hinders nitrogen—boron coordination and allows normal addition of the boron hydrides.

  被磷酸化基团保护的N-烯丙基胺的氨基会阻碍氮-硼配位并允许氢化硼的正常添加。
• 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.