2,2-dimethyl-3-ethoxy-4-(diethylphosphono)-2,5-dihydrofuran | 139731-56-9

• 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: 2,2-dimethyl-3-ethoxy-4-(diethylphosphono)-2,5-dihydrofuran
• 英文别名: 3-diethoxyphosphoryl-4-ethoxy-5,5-dimethyl-2H-furan
• CAS: 139731-56-9
• 化学式: C₁₂H₂₃O₅P
• 分子量: 278.285
• InChiKey: WAUSCSMQAJMILL-UHFFFAOYSA-N

物化性质

• 沸点：
  364.4±42.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-diethoxyphosphoryl-4-methyl-1-methoxy-2,3-pentadiene 以 乙醇 为溶剂， 反应 0.5h， 生成 2,2-dimethyl-3-ethoxy-4-(diethylphosphono)-2,5-dihydrofuran
  参考文献：
  名称：

  Interaction of an allene with polyvalent iodine derivatives. Preparation, x-ray molecular structure, and some reactions of phenyl(2,2-dimethyl-4-(diethylphosphono)-2,5-dihydro-3-furyl)iodonium salts

  摘要：

  Allene 1 reacts with PhIO/BF3.Et2O or PhIF2/BF3.Et2O in CH2Cl2 at -60-degrees-C with the formation of novel phenyldihydrofuryliodonium salts 2. Molecular structures for both products 2a,b are determined by X-ray analysis. Iodonium perchlorate 2b reacts with the anionic nucleophiles (NaN3, NaOCH3, NaOC2H5, CuI/KI) to give the corresponding products of the vinylic nucleophilic substitution (6a-e) of the iodobenzene moiety. However, analogous reaction of 2b with Ph3P gives an unexpected iodide 6e as the major product, along with the usual product of nucleophilic substitution (6d). This result is rationalized by a nucleophilic attack of Ph3P on the iodine atom of the iodonium salt 2b followed by two alternative paths for subsequent ligand coupling.

  DOI：

  10.1021/jo00034a043

文献信息

• Interaction of an allene with polyvalent iodine derivatives. Preparation, x-ray molecular structure, and some reactions of phenyl(2,2-dimethyl-4-(diethylphosphono)-2,5-dihydro-3-furyl)iodonium salts
  作者：N. S. Zefirov、A. S. Koz'min、T. Kasumov、K. A. Potekhin、V. D. Sorokin、V. K. Brel、E. V. Abramkin、Yu. T. Struchkov、V. V. Zhdankin、P. J. Stang

  DOI：10.1021/jo00034a043

  日期：1992.4

  Allene 1 reacts with PhIO/BF3.Et2O or PhIF2/BF3.Et2O in CH2Cl2 at -60-degrees-C with the formation of novel phenyldihydrofuryliodonium salts 2. Molecular structures for both products 2a,b are determined by X-ray analysis. Iodonium perchlorate 2b reacts with the anionic nucleophiles (NaN3, NaOCH3, NaOC2H5, CuI/KI) to give the corresponding products of the vinylic nucleophilic substitution (6a-e) of the iodobenzene moiety. However, analogous reaction of 2b with Ph3P gives an unexpected iodide 6e as the major product, along with the usual product of nucleophilic substitution (6d). This result is rationalized by a nucleophilic attack of Ph3P on the iodine atom of the iodonium salt 2b followed by two alternative paths for subsequent ligand coupling.