N-(diethyloxyphosphoryl)phthalimide | 5022-31-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(diethyloxyphosphoryl)phthalimide
• 英文别名: diethyl (1,3-dioxoisoindolin-2-yl)phosphonate；Diethyl-phthalimido-phosphonat；Diethyl-phthalimidophosphonat, Phthalimido-phosphonsaeure-diethylester；N-(Diethoxyphosphinyl)-phthalimid；diethyl (1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)phosphonate；phthalimido-phosphonic acid diethyl ester；Ditalimphos oxon；2-diethoxyphosphorylisoindole-1,3-dione
• CAS: 5022-31-1
• 化学式: C₁₂H₁₄NO₅P
• 分子量: 283.221
• InChiKey: LEHFUSHLGLJEDB-UHFFFAOYSA-N

物化性质

• 熔点：
  65 °C
• 沸点：
  392.8±25.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  氯磷酸二乙酯 、 potassium phtalimide 以 二氯甲烷 为溶剂， 反应 72.0h， 以43%的产率得到N-(diethyloxyphosphoryl)phthalimide
  参考文献：
  名称：

  Synthesis and evaluation of some variants of the Nefkens’ reagent

  摘要：

  A series of N-substituted phthalimides have been prepared in an effort to explore synthetic variants of the Nefkens' reagent. Three N-acylphthalimides [R = -CH3, -CH2CH3, and -C(CH3)(3)] were prepared and employed for the protection of a series of representative amines. In addition, an N-methanesulfonylphthalimide and N-(diethylphosphoryl)phthalimide were also prepared. It was determined that among the phthalimides that were prepared N-propanoylphthalimide was the most effective reagent for the protection reaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.066

文献信息

• With DBU-activated N-bromophthalimide as potential N-sources to achieve P–N cross-coupling of P(O)–H compounds
  作者：Yueju Li、Fushun Liang

  DOI：10.1016/j.tetlet.2016.05.076

  日期：2016.6

  has been developed with the DBU activation strategy. The nitrogen source may arise from internal N-bromophthalimide itself (a self-immolating reagent) or external phthalimide derivatives (with NBS-DBU activation system). The reaction features broad phosphorous compounds scope, including H-phosphinates, H-phosphonates, and H-phosphine oxides, and short reaction time (less than 10 min). This method provides

  我们已经证明，除了传统的溴化试剂之外，N-卤代酰亚胺还可以用作胺化试剂。本文中，已通过DBU活化策略开发了P（O）-H化合物与N-溴邻苯二甲酰亚胺的P–N交叉偶联。氮源可能来自内部N-溴邻苯二甲酰亚胺本身（自消灭试剂）或外部邻苯二甲酰亚胺衍生物（具有NBS-DBU活化系统）。将反应设有宽磷化合物范围，包括ħ -phosphinates，ħ -phosphonates和ħ-氧化膦，反应时间短（少于10分钟）。该方法为在温和条件下具有生物学重要性的氨基磷酸酯提供了一种简单，方便，有效和绿色的途径。
• Highly Efficient P(III)-to-P(V) Oxidative Rearrangement
  作者：Feng Gao、Karine Auclair

  DOI：10.1080/104265090969270

  日期：2006.1.1

  A rapid and efficient P(III)-to-P(V) intramolecular rearrangement of N-[(phosphino)oxy] amines is reported. This intermediate is generated in situ from the reaction of hydroxylamines with chlorophosphites or chlorophosphoramidites and with rearrangement via the cleavage of the weaker N─O bond to generate a more stable P═O bond. The reaction proceeds spontaneously in an excellent yield when the hydroxylamine

  报道了 N-[(膦基) 氧基] 胺的快速有效的 P(III) 到 P(V) 分子内重排。该中间体是由羟胺与氯亚磷酸酯或氯亚磷酰胺反应原位生成的，并通过断裂较弱的 N-O 键进行重排以生成更稳定的 P=O 键。当羟胺缺电子时，反应以极好的产率自发进行。磷上的各种取代基具有良好的耐受性。
• Efficient synthesis routes for various phthalimido phosphor esters as antimicrobial agents in terms of structure–activity relationship
  作者：Wafaa Mahmoud Abdou、Rizk E. Khidre

  DOI：10.1007/s00706-009-0244-1

  日期：2010.2

  A series of phthalimido phosphor derivatives-alpha-amino-phosphonates, amidophosphonates, phosphonic acid diamides, and oxadiazaphospholes-were prepared by applying different types of phosphorus(III) reagents to 2-methoxy-1H-isoindole-1,3(2H)-dione and 2-anilino-1H-isoindole-1,3(2H)-dione. On the basis of bioassay results, some of the new phosphoryl imides could be considered as lead molecules to be modified in order to improve their antibiotic activity.
• Shaikhiev; Fridland; Mukhutdinova, Russian Journal of General Chemistry, 1999, vol. 69, # 4, p. 557 - 559
  作者：Shaikhiev、Fridland、Mukhutdinova

  DOI：——

  日期：——