2-benzyloxy-2-oxo-1,3,2-dioxaphospholane | 121234-89-7

• 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: 2-benzyloxy-2-oxo-1,3,2-dioxaphospholane
• 英文别名: 2-benzyloxy-[1,3,2]dioxaphospholane-2-oxide；2-Benzyloxy-[1,3,2]dioxaphospholan-2-oxid；1,3,2-Dioxaphospholane, 2-(phenylmethoxy)-, 2-oxide；2-phenylmethoxy-1,3,2λ5-dioxaphospholane 2-oxide
• CAS: 121234-89-7
• 化学式: C₉H₁₁O₄P
• 分子量: 214.158
• InChiKey: GADJIPKTLLPITN-UHFFFAOYSA-N

物化性质

• 熔点：
  49-51 °C
• 沸点：
  307.5±12.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-benzyloxy-2-oxo-1,3,2-dioxaphospholane 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到磷酸乙烯酯
  参考文献：
  名称：

  2,4-Dinitrophenol as an activating reagent in a facile preparation of cyclic phosphate triesters

  摘要：

  2,4-Dinitrophenol was employed with benzyloxy-bis-(diisopropylamino)phosphine to synthesise the cyclic phosphate derivatives of a series of alkane diols (HO-(CH2)(n)-OH, n= 2-6) in good isolated yields. Tetrazole and DNP were compared by P-31 NMR spectroscopy for their ability to catalyse the cyclisation at the P(III) stage. Investigation of the phosphate triester stability under various oxidation and chromatographic conditions resulted in the optimisation of the isolation procedures of the chemically unstable cyclic compounds. Conditions for debenzylation were developed to yield the corresponding cyclic phosphodiesters quantitatively. The methodology was further applied to the preparation and isolation of the cyclic phosphate derivative of a carbohydrate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.101
• 作为产物：
  描述：

  2-Benzyloxy-1,3,2-dioxaphospholan 在 dinitrogen tetraoxide 作用下， 生成 2-benzyloxy-2-oxo-1,3,2-dioxaphospholane
  参考文献：
  名称：

  The Oxidation of Trisubstituted Phosphites by Dinitrogen Tetroxide

  摘要：

  DOI：

  10.1021/ja01553a031

文献信息

• Thermoresponsive Polyphosphoesters Bearing Enzyme-cleavable Side Chains
  作者：Yasuhiko Iwasaki、Takashi Kawakita、Shin-ichi Yusa

  DOI：10.1246/cl.2009.1054

  日期：2009.11.5

  Thermoresponsive polyphosphoesters bearing acetoxymethyl (AM) groups were newly synthesized. The polymers had the LCST-type cloud point in aqueous media, and the thermoresponsive phenomena was influenced by the condition of the medium. About 40% of the AM groups in the polymers were cleaved in contact with esterase for 24 h in phosphate buffer solution. This was significant compared with the spontaneous cleavage in the buffer solution. After the cleavage of the AM groups, the thermoresponsivity of the polyphosphoesters was diminished.

  新近合成了一种带有乙酰氧甲基（AM）基团的热响应性聚磷酸酯。这类高分子在水中表现出LCST型浊点，其热响应现象受介质条件的影响。在磷酸盐缓冲溶液中，与酯酶接触24小时后，约有40%的AM基团被裂解，这一现象显著区别于在缓冲溶液中的自发裂解。AM基团裂解后，聚磷酸酯的热响应性降低了。
• The Oxidation of Trisubstituted Phosphites by Dinitrogen Tetroxide
  作者：James R. Cox、F. H. Westheimer

  DOI：10.1021/ja01553a031

  日期：1958.10
• 2,4-Dinitrophenol as an activating reagent in a facile preparation of cyclic phosphate triesters
  作者：Eric J. Amigues、Marie E. Migaud

  DOI：10.1016/j.tetlet.2003.11.101

  日期：2004.1

  2,4-Dinitrophenol was employed with benzyloxy-bis-(diisopropylamino)phosphine to synthesise the cyclic phosphate derivatives of a series of alkane diols (HO-(CH2)(n)-OH, n= 2-6) in good isolated yields. Tetrazole and DNP were compared by P-31 NMR spectroscopy for their ability to catalyse the cyclisation at the P(III) stage. Investigation of the phosphate triester stability under various oxidation and chromatographic conditions resulted in the optimisation of the isolation procedures of the chemically unstable cyclic compounds. Conditions for debenzylation were developed to yield the corresponding cyclic phosphodiesters quantitatively. The methodology was further applied to the preparation and isolation of the cyclic phosphate derivative of a carbohydrate. (C) 2003 Elsevier Ltd. All rights reserved.