2-Diphenylphosphinoyl-1,3-dioxane | 20570-21-2

• 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-Diphenylphosphinoyl-1,3-dioxane
• 英文别名: (1,3-Dioxan-2-yl)(oxo)diphenyl-lambda~5~-phosphane；2-diphenylphosphoryl-1,3-dioxane
• CAS: 20570-21-2
• 化学式: C₁₆H₁₇O₃P
• 分子量: 288.283
• InChiKey: PYFXDOWLSLTVRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  isopropyl diphenylphosphinite 、 (1,3-Dioxan-2-yl)trimethylammonium iodide 以 甲苯 为溶剂， 反应 3.0h， 以32.6%的产率得到2-Diphenylphosphinoyl-1,3-dioxane
  参考文献：
  名称：

  A solution and solid state conformation of 2-diphenylphosphinoyl-1,3-dioxanes. The nature of O-C-P anomeric interactions.

  摘要：

  Diastereoisomeric 2-diphenylphosphinoyl-1,3-dioxanes 1-4 were synthesized either via the Arbuzov reaction of isopropyl diphenylphosphinite with (1,3-dioxan-2-yl)trimethylammonium iodides or via the transacetalization reaction between 1,3-diols and diphenyl(diethoxymethyl)phosphine oxide. The latter reaction afforded less thermodynamically stable isomers of 3 and 4 in a good yield (44 and 56%, respectively). The magnitude of the anomeric effect in this system determined according to the Franck's equation was found to be 19.7 kJ/mol. Both the NMR and X-ray structural data concerning cis-4,6-dimethyl-1, 3-dioxane derivatives 4 suggest that the anomeric effect could stem from several interactions, including the n(o)-sigma*c-p negative hyperconjugation and intramolecular hydrogen bond formation.

  DOI：

  10.1016/s0040-4020(01)92198-2

文献信息

• JUARISTI, E.;FLORES-VELA, A.;LABASTIDA, V.;ORDONEZ, M., J. PHYS. ORG. CHEM., 2,(1989) N, C. 349-358
  作者：JUARISTI, E.、FLORES-VELA, A.、LABASTIDA, V.、ORDONEZ, M.

  DOI：——

  日期：——
• A solution and solid state conformation of 2-diphenylphosphinoyl-1,3-dioxanes. The nature of O-C-P anomeric interactions.
  作者：Marian Mikołajczyk、Piotr P. Graczyk、Michał W. Wiecorek、Grzegorz Bujacz

  DOI：10.1016/s0040-4020(01)92198-2

  日期：1992.1

  Diastereoisomeric 2-diphenylphosphinoyl-1,3-dioxanes 1-4 were synthesized either via the Arbuzov reaction of isopropyl diphenylphosphinite with (1,3-dioxan-2-yl)trimethylammonium iodides or via the transacetalization reaction between 1,3-diols and diphenyl(diethoxymethyl)phosphine oxide. The latter reaction afforded less thermodynamically stable isomers of 3 and 4 in a good yield (44 and 56%, respectively). The magnitude of the anomeric effect in this system determined according to the Franck's equation was found to be 19.7 kJ/mol. Both the NMR and X-ray structural data concerning cis-4,6-dimethyl-1, 3-dioxane derivatives 4 suggest that the anomeric effect could stem from several interactions, including the n(o)-sigma*c-p negative hyperconjugation and intramolecular hydrogen bond formation.