10,10-dibenzyl-8,9,10,10a-tetrahydrodipyrido[2,1-b:3',2'-e][1,3]oxazin-5(7H)-one | 1416767-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 10,10-dibenzyl-8,9,10,10a-tetrahydrodipyrido[2,1-b:3',2'-e][1,3]oxazin-5(7H)-one
• 英文别名: 11,11-Dibenzyl-9-oxa-1,7-diazatricyclo[8.4.0.03,8]tetradeca-3(8),4,6-trien-2-one；11,11-dibenzyl-9-oxa-1,7-diazatricyclo[8.4.0.03,8]tetradeca-3(8),4,6-trien-2-one
• CAS: 1416767-45-7
• 化学式: C₂₅H₂₄N₂O₂
• 分子量: 384.478
• InChiKey: VCCQZJOMUSKLKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-Boc-2-哌啶酮 在 三乙基硼氢化锂 、 1-丙基磷酸酐 、 N,N-二异丙基乙胺 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 23.83h， 生成 10,10-dibenzyl-8,9,10,10a-tetrahydrodipyrido[2,1-b:3',2'-e][1,3]oxazin-5(7H)-one
  参考文献：
  名称：

  Direct Imine Acylation: Rapid Access to Diverse Heterocyclic Scaffolds

  摘要：

  A simple and efficient procedure to prepare a range of diverse heterocycles by the direct acylation of imines using a variety of functionalized benzoic acids is described. The methodology features a novel method for N-acyliminium ion generation followed by in situ intramolecular trapping by oxygen-, nitrogen-, sulfur- and carbon-based nucleophiles. Preliminary mechanistic studies, using ReactIR, are also reported.

  DOI：

  10.1021/ol303073b

文献信息

• Substrate scope in the direct imine acylation of ortho-substituted benzoic acid derivatives: the total synthesis (±)-cavidine
  作者：Christiana Kitsiou、William P. Unsworth、Graeme Coulthard、Richard J.K. Taylor

  DOI：10.1016/j.tet.2014.04.066

  日期：2014.10

  The direct imine acylation (DIA) and subsequent cyclisation of a range of imines with ortho-substituted benzoic acid derivatives is described. Variation in the coupling reagents, imine and benzoic acid were all examined. The DIA procedure was also applied in the total synthesis of (±)-cavidine.

  描述了直接亚胺酰化（DIA）和随后的一系列亚胺与邻位取代的苯甲酸衍生物的环化。均检查了偶联剂亚胺和苯甲酸的变化。DIA方法也被用于（±）-cavidine的全合成。
• Direct Imine Acylation: Rapid Access to Diverse Heterocyclic Scaffolds
  作者：William P. Unsworth、Christiana Kitsiou、Richard J. K. Taylor

  DOI：10.1021/ol303073b

  日期：2013.1.18

  A simple and efficient procedure to prepare a range of diverse heterocycles by the direct acylation of imines using a variety of functionalized benzoic acids is described. The methodology features a novel method for N-acyliminium ion generation followed by in situ intramolecular trapping by oxygen-, nitrogen-, sulfur- and carbon-based nucleophiles. Preliminary mechanistic studies, using ReactIR, are also reported.