4-(tert-butoxycarbonyl)-3,5-diphenyl-2-formyl-4H-[1,4]oxazine | 943818-50-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(tert-butoxycarbonyl)-3,5-diphenyl-2-formyl-4H-[1,4]oxazine
• 英文别名: 4-(tert-butoxycarbonyl)-3,5-diphenyl-2-formyl-[1,4]-oxazine；Tert-butyl 2-formyl-3,5-diphenyl-1,4-oxazine-4-carboxylate
• CAS: 943818-50-6
• 化学式: C₂₂H₂₁NO₄
• 分子量: 363.413
• InChiKey: JFCMNNPWKWJRPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(tert-butoxycarbonyl)-3,5-diphenyl-2-formyl-4H-[1,4]oxazine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以99%的产率得到4-(tert-butoxycarbonyl)-2-hydroxymethyl-3,5-diphenyl-[1,4]-oxazine
  参考文献：
  名称：

  Access to novel bicyclic fused γ-butyrolactone using [3,3]-sigmatropic rearrangement and acid-lactonization sequence as key transformation

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2010.04.041
• 作为产物：
  描述：

  3,5-bis{[bis(phenyloxy)phosphoryl]oxy}-4-(tert-butoxycarbonyl)-[1,4]oxazine 在 bis-triphenylphosphine-palladium(II) chloride 六甲基磷酰三胺 、 barium dihydroxide 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 为溶剂， 反应 10.92h， 生成 4-(tert-butoxycarbonyl)-3,5-diphenyl-2-formyl-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