3,5,8-triphenyl-4,9-dioxa-1,2,6,7-tetraaza-5λ⁵-phospha-spiro[4.4]nona-2,7-diene | 62762-05-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5,8-triphenyl-4,9-dioxa-1,2,6,7-tetraaza-5λ⁵-phospha-spiro[4.4]nona-2,7-diene
• 英文别名: 2,5,7-Triphenyl-1,6-dioxa-3,4,8,9-tetraza-5lambda5-phosphaspiro[4.4]nona-2,7-diene；2,5,7-triphenyl-1,6-dioxa-3,4,8,9-tetraza-5λ5-phosphaspiro[4.4]nona-2,7-diene
• CAS: 62762-05-4
• 化学式: C₂₀H₁₇N₄O₂P
• 分子量: 376.354
• InChiKey: MNLDWMFHINDQDL-UHFFFAOYSA-N

物化性质

• 熔点：
  240-242 °C

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯甲酰肼 、 苯基硫代膦酰二氯 以 甲苯 为溶剂， 生成 3,5,8-triphenyl-4,9-dioxa-1,2,6,7-tetraaza-5λ⁵-phospha-spiro[4.4]nona-2,7-diene
  参考文献：
  名称：

  Schmidpeter,A.; Luber,J., Chemische Berichte, 1977, vol. 110, p. 1124 - 1129

  摘要：

  DOI：

文献信息

• Symmetrical spiro-phosphoroheterocycles from the selenation of carbohydrazides
  作者：Guoxiong Hua、David B. Cordes、Yang Li、Alexandra M.Z. Slawin、J. Derek Woollins

  DOI：10.1016/j.tetlet.2011.04.058

  日期：2011.6

  new symmetrical spiro heterocycles in 48–76% isolated yields. However, under identical conditions, treating Woollins’ reagent with thiophene-2-carbohydrazide leads to an additional product, 1,3,4-selenadiazole (27% yield) together with the spiro phosphorus heterocycle in 44% yield. Three representative X-ray structures are reported.

  2,4-双（苯基）-1,3-二硒二膦2,4-二硒化物（Woollins试剂）在回流的甲苯中与苯甲酰肼反应生成新的对称螺环杂环，分离产率为48-76％。但是，在相同的条件下，用噻吩-2-碳酰肼处理Woollins试剂可得到另一种产物1,3,4-硒代二唑（27％的产率）和螺磷杂环，产率为44％。报告了三个代表性的X射线结构。
• A phosphoryl to spiro-bicyclophosphorane transformation via β-amidic proton elimination in phosphorylated hydrazides
  作者：Khodayar Gholivand、Hamid R. Mahzouni、Foroogh Molaei、Ali A. Kalateh

  DOI：10.1016/j.tetlet.2012.08.105

  日期：2012.10

  The reaction between phosphoryl-containing reagents and hydrazides has been studied. The tetrahedral phosphoryl structure is transformed into a spiro-bicyclophosphorane system with trigonal bipyramidal geometry by the elimination of a beta-amidic proton in the reaction between a hydrazide and phosphoryl reagents with at least two leaving groups (Cl) bound to the phosphorus atom, such as POCl3 or PhPOCl2. In the spiro-bicyclophosphorane structure, the C=N imine bond is formed upon beta-amidic proton elimination, leading to the conversion of the C=O into a C-O bond and the formation of a P-O bond. All of these structural rearrangements are supported by X-ray crystallography data, and NMR and IR experiments. (C) 2012 Elsevier Ltd. All rights reserved.