2-azido-5,5-dimethyl-1,3,2-dioxaphosphorinane-2-oxide

• 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: 2-azido-5,5-dimethyl-1,3,2-dioxaphosphorinane-2-oxide
• 英文别名: 2-azido-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide；2-Azido-5,5-dimethyl-1,3,2lambda5-dioxaphosphinane 2-oxide；2-azido-5,5-dimethyl-1,3,2λ5-dioxaphosphinane 2-oxide
• 化学式: C₅H₁₀N₃O₃P
• 分子量: 191.126
• InChiKey: ABNICAZKJVCGIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-azido-5,5-dimethyl-1,3,2-dioxaphosphorinane-2-oxide 、 2-乙酰苯甲酸 在 N,N-二异丙基乙胺 作用下， 以40%的产率得到4-((5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)oxy)quinolin-2(1H)-one
  参考文献：
  名称：

  由2-酰基苯甲酸合成1,2-二氢-2-氧代-4-喹啉基磷酸酯。

  摘要：

  我们报告了通过一锅级联反应在磷酰叠氮化物存在下从2-酰基-苯甲酸（2a-1）开始合成1,2-二氢-2-羰基-4-喹啉基磷酸（1a-1）的方法该反应涉及Curtius重排，烯醇碳到异氰酸酯中间体的分子内亲核加成以及烯醇氧到磷酰叠氮化物的加成消除。在反应过程中，在温和的条件下形成了三个新的键，以适度的产率得到1,2-二氢-2-氧代-4-喹啉基磷酸酯。

  DOI：

  10.1016/j.tetlet.2015.01.188
• 作为产物：
  描述：

  2,2-二甲基-1,3-丙二醇 在 三乙胺 、 三氯氧磷 、 sodium azide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 10.0h， 以40%的产率得到2-azido-5,5-dimethyl-1,3,2-dioxaphosphorinane-2-oxide
  参考文献：
  名称：

  Phosphoryl Azides as Versatile New Reaction Partners in the Cu-Catalyzed Three-Component Couplings

  摘要：

  [GRAPHICS]Phosphoryl azide was successfully employed as an efficient reacting partner in the Cu-catalyzed three-component reaction with 1-alkynes and amines to produce the corresponding phosphoryl amidines in high yields. A range of fruitful applicability of the produced amidines was also demonstrated such as an alkoxide exchange and asymmetric alpha-alkylation of optically active BINOL-derived amidines.

  DOI：

  10.1021/jo7016247

文献信息

• Synthesis of Phosphoramidates: A Facile Approach Based on the C–N Bond Formation via Ir-Catalyzed Direct C–H Amidation
  作者：Hyunwoo Kim、Juhyeon Park、Jeung Gon Kim、Sukbok Chang

  DOI：10.1021/ol502722j

  日期：2014.10.17

  A new synthetic route to phosphoramidates by intermolecular C-H amidation is presented. Substrates with assorted directing groups were activated by an iridium-based catalyst system and reacted with a number of phosphoryl azides, executing efficient phosphoramidate synthesis via C-N bond formations.
• Phosphoryl Azides as Versatile New Reaction Partners in the Cu-Catalyzed Three-Component Couplings
  作者：Seok Hwan Kim、Doo Young Jung、Sukbok Chang

  DOI：10.1021/jo7016247

  日期：2007.12.1

  [GRAPHICS]Phosphoryl azide was successfully employed as an efficient reacting partner in the Cu-catalyzed three-component reaction with 1-alkynes and amines to produce the corresponding phosphoryl amidines in high yields. A range of fruitful applicability of the produced amidines was also demonstrated such as an alkoxide exchange and asymmetric alpha-alkylation of optically active BINOL-derived amidines.
• Synthesis of 1,2-dihydro-2-oxo-4-quinolinyl phosphates from 2-acyl-benzoic acids
  作者：Xinhua He、Tharcilla Aglio、Jeffrey R. Deschamps、Rachita Rai、Fengtian Xue

  DOI：10.1016/j.tetlet.2015.01.188

  日期：2015.3

  2-acyl-benzoic acids (2a-l) in the presence of phosphoryl azides via a one-pot cascade reaction involving a Curtius rearrangement, an intramolecular nucleophilic addition of the enol carbon to the isocyanate intermediate, and an addition-elimination of the enol oxygen to the phosphoryl azide. During the reaction three new bonds are formed under mild conditions to yield 1,2-dihydro-2-oxo-4-quinolinyl phosphates

  我们报告了通过一锅级联反应在磷酰叠氮化物存在下从2-酰基-苯甲酸（2a-1）开始合成1,2-二氢-2-羰基-4-喹啉基磷酸（1a-1）的方法该反应涉及Curtius重排，烯醇碳到异氰酸酯中间体的分子内亲核加成以及烯醇氧到磷酰叠氮化物的加成消除。在反应过程中，在温和的条件下形成了三个新的键，以适度的产率得到1,2-二氢-2-氧代-4-喹啉基磷酸酯。