8-Allyl-1-methyl-12-oxa-8-aza-tricyclo[7.2.1.0^2,7]dodeca-2,4,6-triene | 748771-49-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 8-Allyl-1-methyl-12-oxa-8-aza-tricyclo[7.2.1.0^2,7]dodeca-2,4,6-triene
• 英文别名: 1-Methyl-8-prop-2-enyl-12-oxa-8-azatricyclo[7.2.1.02,7]dodeca-2,4,6-triene；1-methyl-8-prop-2-enyl-12-oxa-8-azatricyclo[7.2.1.02,7]dodeca-2,4,6-triene
• CAS: 748771-49-5
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: QVCNGEUQQJEODW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-Allyl-1-methyl-12-oxa-8-aza-tricyclo[7.2.1.0^2,7]dodeca-2,4,6-triene 在 四(三苯基膦)钯 对甲苯亚磺酸 作用下， 以 二氯甲烷 为溶剂， 以55%的产率得到1-Methyl-12-oxa-8-azatricyclo[7.2.1.02,7]dodeca-2,4,6-triene
  参考文献：
  名称：

  N-Allyl-1,3-oxazines via a facile keto-ene/cyclization tandem reaction

  摘要：

  The intramolecular keto-ene/cyclization tandem reaction of gamma-N-allylamino ketones is an effective means of producing 1,3-oxazines. The reaction usually requires high temperatures and/or pressures. We discovered that N,N-diallyl amines undergo the reaction at lower temperatures than their monoallyl analogs. An extreme example, 1-N,N-diallylamino-9,10-anthraquinone, undergoes the keto-ene reaction near ambient temperature. In the case of 1-N,N'-dialkylaminoanthraquinones, electron deficient ene components can even be used, allowing the preparation of a broad spectrum of oxazines. Furthermore, the N-allyl-1,3-oxazine can be easily deallylated to produce a 1,3-oxazine that contains a secondary amine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.049
• 作为产物：
  描述：

  2-(N,N-diallylamino)-acetophenone 以 均三甲苯 为溶剂， 反应 120.0h， 以68%的产率得到8-Allyl-1-methyl-12-oxa-8-aza-tricyclo[7.2.1.0^2,7]dodeca-2,4,6-triene
  参考文献：
  名称：

  N-Allyl-1,3-oxazines via a facile keto-ene/cyclization tandem reaction

  摘要：

  The intramolecular keto-ene/cyclization tandem reaction of gamma-N-allylamino ketones is an effective means of producing 1,3-oxazines. The reaction usually requires high temperatures and/or pressures. We discovered that N,N-diallyl amines undergo the reaction at lower temperatures than their monoallyl analogs. An extreme example, 1-N,N-diallylamino-9,10-anthraquinone, undergoes the keto-ene reaction near ambient temperature. In the case of 1-N,N'-dialkylaminoanthraquinones, electron deficient ene components can even be used, allowing the preparation of a broad spectrum of oxazines. Furthermore, the N-allyl-1,3-oxazine can be easily deallylated to produce a 1,3-oxazine that contains a secondary amine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.049

文献信息

• N-Allyl-1,3-oxazines via a facile keto-ene/cyclization tandem reaction
  作者：Robert G Brinson、Paul B Jones

  DOI：10.1016/j.tetlet.2004.06.049

  日期：2004.8

  The intramolecular keto-ene/cyclization tandem reaction of gamma-N-allylamino ketones is an effective means of producing 1,3-oxazines. The reaction usually requires high temperatures and/or pressures. We discovered that N,N-diallyl amines undergo the reaction at lower temperatures than their monoallyl analogs. An extreme example, 1-N,N-diallylamino-9,10-anthraquinone, undergoes the keto-ene reaction near ambient temperature. In the case of 1-N,N'-dialkylaminoanthraquinones, electron deficient ene components can even be used, allowing the preparation of a broad spectrum of oxazines. Furthermore, the N-allyl-1,3-oxazine can be easily deallylated to produce a 1,3-oxazine that contains a secondary amine. (C) 2004 Elsevier Ltd. All rights reserved.