2-oxo-2-ethoxy-1,2-oxaphospholane | 1193-39-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 2-oxo-2-ethoxy-1,2-oxaphospholane
• 英文别名: 2-ethoxy-1,2-oxaphospholane 2-oxide；2-ethoxy-1,2λ5-oxaphospholane 2-oxide
• CAS: 1193-39-1
• 化学式: C₅H₁₁O₃P
• 分子量: 150.114
• InChiKey: KBESTWHNVGVDHD-UHFFFAOYSA-N

物化性质

• 沸点：
  208.9±7.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-oxo-2-ethoxy-1,2-oxaphospholane 生成 3-Hydroxy-propanphosphonsaeure-mono-ethyl-ester
  参考文献：
  名称：

  Hydrolysis of Phostonates^1,2

  摘要：

  DOI：

  10.1021/ja01080a021
• 作为产物：
  描述：

  二乙基(3-溴丙基)膦酸酯 反应 2.0h， 以66%的产率得到2-oxo-2-ethoxy-1,2-oxaphospholane
  参考文献：
  名称：

  环状和无环磷酸酯和膦酸酯的反应热。应变差异和空间阻滞

  摘要：

  与无环类似物相比，五元环状磷酸酯水解速率的百万倍增加纯粹是焓，并且至少部分是由于与无环类似物相比四配位环状反应物的不稳定，假设两者与氢氧化物反应通过无应变的五坐标过渡态。环状和非环状磷酸酯和膦酸酯水解的量热分析报告，其中环状和非环状物质的水解焓差异的绝对值远小于活化焓的差异（约 2 kcal/mol 差异）

  DOI：

  10.1021/ja00034a045

文献信息

• Synthesis of γ-hydroxypropyl P-chirogenic (±)-phosphorus oxide derivatives by regioselective ring-opening of oxaphospholane 2-oxide precursors
  作者：Iris Binyamin、Shoval Meidan-Shani、Nissan Ashkenazi

  DOI：10.3762/bjoc.11.143

  日期：——

  The synthesis of P-chirogenic (+/-)-phosphine oxides and phosphinates via selective nucleophilic ring opening of the corresponding oxaphospholanes is described. Two representative substrates: the phosphonate 2-ethoxy-1,2-oxaphospholane 2-oxide and the phosphinate 2-phenyl-1,2-oxaphospholane 2-oxide were reacted with various Grignard reagents to produce a single alkyl/aryl product. These products may

  描述了通过相应的氧杂膦酮的选择性亲核开环来合成P-生色（+/-）-氧化膦和次膦酸酯。使两种代表性的底物：膦酸酯2-乙氧基-1，2-氧杂膦烷2-氧化物和次膦酸酯2-苯基-1，2-氧杂膦烷2-氧化物与各种格氏试剂反应以产生单一的烷基/芳基产物。除了由开环产生的磷中心如γ-羟丙基和由格氏试剂衍生的π供体基团如芳基，烯丙基，炔丙基和烯丙基以外，这些产物还可具有其他功能。
• Pudovik,A.N. et al., Journal of general chemistry of the USSR, 1964, vol. 34, p. 2604 - 2607
  作者：Pudovik,A.N. et al.

  DOI：——

  日期：——
• ω-haloalkylphosphoryl compounds: Synthesis and properties
  作者：V. V. Ragulin

  DOI：10.1134/s1070363212120055

  日期：2012.12

  A general method of the synthesis of omega-haloalkylphosphoryl compounds was developed, a series of compounds of phosphonic and phosphine oxide type were synthesized. The ability of some omega-haloalkylphosphonates to undergo intramolecular cyclization into the corresponding 1,2-oxaphospholane and 1,2-oxaphosphorine was investigated depending on the solvent polarity, the presence of halogen ions in the solution, and temperature. Tetrahydrofuran was chosen as one of the most suitable solvents for the alkylation of CH acids with omega-haloalkylphosphoryl compounds.
• Kluger, Ronald; Taylor, Scott D., Journal of the American Chemical Society, 1990, vol. 112, # 18, p. 6669 - 6671
  作者：Kluger, Ronald、Taylor, Scott D.

  DOI：——

  日期：——
• RAPID AND EFFICIENT ARBUZOV REACTION UNDER MICROWAVE IRRADIATION
  作者：Didier Villemin、Fabrice Simeon、Hugues Decreus、Paul-Alain Jaffres

  DOI：10.1080/10426509808032465

  日期：1998.1

  Diethyl alkylphosphonates are efficiently and rapidly prepared in good yields (75-99%) from trialkylphosphates and alkyl halides under short microwaves irradiations.