2,3,4,2',3',4'-Hexamethyl-[2,2']bioxazolidinyl | 141916-12-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 2,3,4,2',3',4'-Hexamethyl-[2,2']bioxazolidinyl
• 英文别名: 2,3,4-Trimethyl-2-(2,3,4-trimethyl-1,3-oxazolidin-2-yl)-1,3-oxazolidine
• CAS: 141916-12-3
• 化学式: C₁₂H₂₄N₂O₂
• 分子量: 228.335
• InChiKey: CXEIPQYHJSGUDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  24.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (3S,4aS,7S,8aS)-3,4a,7,8a-Tetramethyl-octahydro-[1,4]oxazino[3,2-b][1,4]oxazine 、 硫酸二甲酯 反应 0.5h， 生成 2,3,4,2',3',4'-Hexamethyl-[2,2']bioxazolidinyl 、 (3R,4aS,7R,8aS)-3,4,4a,7,8,8a-Hexamethyl-octahydro-[1,4]oxazino[3,2-b][1,4]oxazine 、 (3S,4aS,7S,8aS)-3,4,4a,7,8,8a-Hexamethyl-octahydro-[1,4]oxazino[3,2-b][1,4]oxazine
  参考文献：
  名称：

  Stereoelectronic effects in the conformational behavior and ring formation of some N,N′-dimethyl- and N,N′-diacetyl- 1,5-dioxa-4,8-diazadecalins.

  摘要：

  A series of 4,8-dimethyl- and 4,8-diacetyl-cis-octahydro-[1,4]oxazino[3,2-b]-1,4-oxazines (title compounds) 4 and 7 respectively, were synthesized and studied using H-1- and C-13-NMR techniques. Conformational analysis of 4 showed a strong preference for conformers possessing an anti-N/gauche-O array vs an anti-O/gauche-N relationship (DELTA-G(O) = 0.88 Kcal/mol). However 7b exists exclusively as an anti-O/gauche-N conformer with a free energy of activation for the amide rotation barrier of 11.6 Kcal/mol (248 K). The stereoelectronic features of the C-N-C-O-C moieties of 4 and 7 are emphasized. A general reaction pathway is also discussed.

  DOI：

  10.1016/s0040-4020(01)88531-8

文献信息

• Stereoelectronic effects in the conformational behavior and ring formation of some N,N′-dimethyl- and N,N′-diacetyl- 1,5-dioxa-4,8-diazadecalins.
  作者：Benito Alcaide、Jesús Jimenez-Barbero、Joaquin Plumet、Ignacio M. Rodriguez-Campos

  DOI：10.1016/s0040-4020(01)88531-8

  日期：1992.3

  A series of 4,8-dimethyl- and 4,8-diacetyl-cis-octahydro-[1,4]oxazino[3,2-b]-1,4-oxazines (title compounds) 4 and 7 respectively, were synthesized and studied using H-1- and C-13-NMR techniques. Conformational analysis of 4 showed a strong preference for conformers possessing an anti-N/gauche-O array vs an anti-O/gauche-N relationship (DELTA-G(O) = 0.88 Kcal/mol). However 7b exists exclusively as an anti-O/gauche-N conformer with a free energy of activation for the amide rotation barrier of 11.6 Kcal/mol (248 K). The stereoelectronic features of the C-N-C-O-C moieties of 4 and 7 are emphasized. A general reaction pathway is also discussed.