2-ethyl-6,6-dimethyl-6,7-dihydrobenzo[d]oxazol-4(5H)-one | 1139690-30-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-ethyl-6,6-dimethyl-6,7-dihydrobenzo[d]oxazol-4(5H)-one
• 英文别名: 6,6-dimethyl-2-ethyl-6,7-dihydro-1,3-benzoxazol-4(5H)-one；2-ethyl-6,6-dimethyl-5,7-dihydro-1,3-benzoxazol-4-one
• CAS: 1139690-30-4
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: XGHQCKBGNIFKTN-UHFFFAOYSA-N

物化性质

• 沸点：
  284.2±9.0 °C(predicted)
• 密度：
  1.073±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-ethyl-6,6-dimethyl-6,7-dihydrobenzo[d]oxazol-4(5H)-one 在 盐酸 作用下， 以 水 为溶剂， 反应 0.5h， 以88%的产率得到2-aminodimedone hydrochloride
  参考文献：
  名称：

  Synthesis of benzimidazolone derivatives based on 2-acylcyclohexane-1,3-diones alkoximes

  摘要：

  2-(1-Alkoxyiminoalkyl)cyclohexane-1,3-diones undergo at heating Beckmann rearrangement to give 6,7-dihydro-1,3-benzoxazol-4(5H)-one derivatives that under treatment with amines in acid medium are converted into 1,5,6,7-tetrahydro-4H-benzimidazol-4-ones. In reaction of 6,7-dihydro-1,3-benzoxazol-4(5H)- ones with O-ethylhydroxylamine 4-ethoxyimino derivatives were obtained that treated with hydrochloric acid formed the corresponding N-ethoxybenzimidazolones.

  DOI：

  10.1134/s1070428008070130
• 作为产物：
  描述：

  以 乙醇 为溶剂， 反应 24.0h， 以81%的产率得到2-ethyl-6,6-dimethyl-6,7-dihydrobenzo[d]oxazol-4(5H)-one
  参考文献：
  名称：

  Synthesis of benzimidazolone derivatives based on 2-acylcyclohexane-1,3-diones alkoximes

  摘要：

  2-(1-Alkoxyiminoalkyl)cyclohexane-1,3-diones undergo at heating Beckmann rearrangement to give 6,7-dihydro-1,3-benzoxazol-4(5H)-one derivatives that under treatment with amines in acid medium are converted into 1,5,6,7-tetrahydro-4H-benzimidazol-4-ones. In reaction of 6,7-dihydro-1,3-benzoxazol-4(5H)- ones with O-ethylhydroxylamine 4-ethoxyimino derivatives were obtained that treated with hydrochloric acid formed the corresponding N-ethoxybenzimidazolones.

  DOI：

  10.1134/s1070428008070130

文献信息

• Cu(II)-catalyzed synthesis of 2,4,5-trisubstituted oxazoles
  作者：S. Prashanth、D.R. Adarsh、Rajashaker Bantu、Balasubramanian Sridhar、B.V. Subba Reddy

  DOI：10.1016/j.tetlet.2022.154252

  日期：2022.12

  for the synthesis of 2,4,5-trisubstituted oxazoles has been developed from the direct coupling of α-diazoketones with aryl or alkyl nitriles. The reaction proceeds through the formation of nitrilium ion by the nucleophic addition of nitrile onto diazo functionality followed by an intramolecular trapping of nitrilium ion by keto group. Both aryl, and alkyl nitriles underwent smooth cyclocondensation

  通过将 α-重氮酮与芳基或烷基腈直接偶联，开发了一种铜催化的简单有效的 2,4,5-三取代恶唑合成方案。通过将腈亲核加成到重氮官能团上，然后通过酮基在分子内捕获腈离子，反应通过形成腈离子进行。芳基腈和烷基腈均与重氮化合物顺利环化缩合，以优异的收率得到三取代的恶唑。