3aH,9H,9aH-trihydro-3,10,10-trimethyl<3>benzopyrano<3,2-d>-1,2-oxazine N-oxide | 142840-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3aH,9H,9aH-trihydro-3,10,10-trimethyl<3>benzopyrano<3,2-d>-1,2-oxazine N-oxide
• 英文别名: 1,4,4-trimethyl-2-oxido-5,10b-dihydro-4aH-chromeno[4,3-d]oxazin-2-ium
• CAS: 142840-19-5
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: AJVMAFXQAQCBAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 均三甲苯 为溶剂， 反应 4.5h， 生成 3aH,9H,9aH-trihydro-3,10,10-trimethyl<3>benzopyrano<3,2-d>-1,2-oxazine N-oxide
  参考文献：
  名称：

  Inter- and intramolecular [4 + 2] cycloadditions of nitroalkenes with olefins. 2-Nitrostyrenes

  摘要：

  Aromatic nitroalkenes 9-12 underwent Lewis acid catalyzed cycloadditions with various cyclic alkenes to afford high yields of nitronates 25-30 with exclusive anti selectivity. Hammett studies helped to further delineate the role of the Lewis acid. Reaction of nitroalkenes 8 and 10 with various cyclic dienes in the presence of a Lewis acid demonstrated the ability of nitroalkenes to behave as dienes in cycloadditions. The major products were the syn diastereomers which arise from an endo-folded transition structure. Finally, intramolecular cycloaddition of 36-39 allowed a correlation between the stereochemical course of the reaction and positions of sp2 centers in the tether to be addressed.

  DOI：

  10.1021/jo00044a029

文献信息

• Inter- and intramolecular [4 + 2] cycloadditions of nitroalkenes with olefins. 2-Nitrostyrenes
  作者：Scott E. Denmark、Brenda S. Kesler、Young Choon Moon

  DOI：10.1021/jo00044a029

  日期：1992.8

  Aromatic nitroalkenes 9-12 underwent Lewis acid catalyzed cycloadditions with various cyclic alkenes to afford high yields of nitronates 25-30 with exclusive anti selectivity. Hammett studies helped to further delineate the role of the Lewis acid. Reaction of nitroalkenes 8 and 10 with various cyclic dienes in the presence of a Lewis acid demonstrated the ability of nitroalkenes to behave as dienes in cycloadditions. The major products were the syn diastereomers which arise from an endo-folded transition structure. Finally, intramolecular cycloaddition of 36-39 allowed a correlation between the stereochemical course of the reaction and positions of sp2 centers in the tether to be addressed.