2-N,N-Dimethylamino-cis-4,6-dimethyl-1,3-dioxane | 142572-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 2-N,N-Dimethylamino-cis-4,6-dimethyl-1,3-dioxane
• 英文别名: (4S,6R)-N,N,4,6-tetramethyl-1,3-dioxan-2-amine
• CAS: 142572-25-6；142632-73-3
• 化学式: C₈H₁₇NO₂
• 分子量: 159.228
• InChiKey: AHLAVEXNVBEVMU-DHBOJHSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-N,N-Dimethylamino-cis-4,6-dimethyl-1,3-dioxane 以 乙醚 、 甲苯 为溶剂， 反应 3.0h， 生成 r-2-Diphenylphosphinoyl-t-4,t-6-dimethyl-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
• 作为产物：
  描述：

  N,N-二甲基甲酰胺二甲基缩醛 、 2,4-戊二醇 以87.9%的产率得到2-N,N-Dimethylamino-cis-4,6-dimethyl-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