4-(tert-butoxycarbonyl)-3,5-diphenyl-4H-[1,4]oxazine | 943818-42-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(tert-butoxycarbonyl)-3,5-diphenyl-4H-[1,4]oxazine
• 英文别名: 4-(tert-butoxycarbonyl)-3,5-diphenyl-[1,4]-oxazine；Tert-butyl 3,5-diphenyl-1,4-oxazine-4-carboxylate
• CAS: 943818-42-6
• 化学式: C₂₁H₂₁NO₃
• 分子量: 335.403
• InChiKey: JAHGAQQYTCUIJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(tert-butoxycarbonyl)-3,5-diphenyl-4H-[1,4]oxazine 在 六甲基磷酰三胺 、 正丁基锂 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.92h， 以95%的产率得到4-(tert-butoxycarbonyl)-3,5-diphenyl-2-iodo-4H-[1,4]oxazine
  参考文献：
  名称：

  Easy Access to New Heterocyclic Systems:  1,4-Oxazine and Substituted 1,4-Oxazines

  摘要：

  In the course of our investigations on the synthesis of new nitrogen heterocyclic derivatives, we were interested in the synthesis and study of new 1,4-oxazine rings. To this aim, the desired bisvinylphosphate was prepared from N-Boc morpholine-3,5-dione and was then engaged in palladium-catalyzed reactions (reduction, Suzuki, and Stille cross-coupling reactions). The 1,4-oxazine and its corresponding 3,5-disubstituted derivatives were obtained in fair to good yields and were then functionalized under anionic conditions.

  DOI：

  10.1021/jo070528n
• 作为产物：
  描述：

  4-(tert-butoxycarbonyl)-morpholine-3,5-dione 在 bis-triphenylphosphine-palladium(II) chloride 六甲基磷酰三胺 、 barium dihydroxide 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 9.33h， 生成 4-(tert-butoxycarbonyl)-3,5-diphenyl-4H-[1,4]oxazine
  参考文献：
  名称：

  Easy Access to New Heterocyclic Systems:  1,4-Oxazine and Substituted 1,4-Oxazines

  摘要：

  In the course of our investigations on the synthesis of new nitrogen heterocyclic derivatives, we were interested in the synthesis and study of new 1,4-oxazine rings. To this aim, the desired bisvinylphosphate was prepared from N-Boc morpholine-3,5-dione and was then engaged in palladium-catalyzed reactions (reduction, Suzuki, and Stille cross-coupling reactions). The 1,4-oxazine and its corresponding 3,5-disubstituted derivatives were obtained in fair to good yields and were then functionalized under anionic conditions.

  DOI：

  10.1021/jo070528n

文献信息

• Access to novel bicyclic fused γ-butyrolactone using [3,3]-sigmatropic rearrangement and acid-lactonization sequence as key transformation
  作者：Elise Claveau、Erwan Noirjean、Pascal Bouyssou、Gérard Coudert、Isabelle Gillaizeau

  DOI：10.1016/j.tetlet.2010.04.041

  日期：2010.6

  In this Letter, we wish to disclose a new strategy for the construction of substituted gamma-butyrolactones. The latter might not only be of potential interest in terms of biological activity and synthesis but also allow access to original heterocyclic scaffolds. According to previous study, efficient two-step sequence involving Eschenmoser-Claisen rearrangement and acid-lactonization reaction was successfully applied for the construction of original fused bicyclic gamma-butyrolactones based on an 1.4-oxazine core. (C) 2010 Elsevier Ltd. All rights reserved.