(E)-6-azido-3-methyl-3-hexen-2-one | 823805-88-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-6-azido-3-methyl-3-hexen-2-one
• 英文别名: (E)-6-azido-3-methylhex-3-en-2-one
• CAS: 823805-88-5
• 化学式: C₇H₁₁N₃O
• 分子量: 153.184
• InChiKey: LDIRFQQAZWXUBX-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-6-azido-3-methyl-3-hexen-2-one 、 1,3-环己二烯 在 甲基二氯化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 14.0h， 以72%的产率得到(+/-)-6-methyl-6-acetyl-5-(2-azidoethyl)-bicyclo[2.2.2]oct-2-ene
  参考文献：
  名称：

  Domino Reactions That Combine an Azido-Schmidt Ring Expansion with the Diels−Alder Reaction

  摘要：

  The combination of the intramolecular Schmidt reaction with the Diels-Alder reaction provides expedient access to a variety of heterocycles. Two different modes of reaction planning are presented. In one, the azide and ketone moieties necessary for the intramolecular Schmidt reaction originate on different molecules that are reacted and subsequently undergo a ring-adjustment step. Alternatively, an azido ketone can be used provided the ketone is deactivated by its presence in an enone.

  DOI：

  10.1021/ol047809r
• 作为产物：
  描述：

  3-叠氮丙醛 、 diethyl (3-oxobutan-2-yl)phosphonate 在 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以20%的产率得到(E)-6-azido-3-methyl-3-hexen-2-one
  参考文献：
  名称：

  Domino Reactions That Combine an Azido-Schmidt Ring Expansion with the Diels−Alder Reaction

  摘要：

  The combination of the intramolecular Schmidt reaction with the Diels-Alder reaction provides expedient access to a variety of heterocycles. Two different modes of reaction planning are presented. In one, the azide and ketone moieties necessary for the intramolecular Schmidt reaction originate on different molecules that are reacted and subsequently undergo a ring-adjustment step. Alternatively, an azido ketone can be used provided the ketone is deactivated by its presence in an enone.

  DOI：

  10.1021/ol047809r

文献信息

• Domino Reactions That Combine an Azido-Schmidt Ring Expansion with the Diels−Alder Reaction
  作者：Yibin Zeng、D. Srinivasa Reddy、Erin Hirt、Jeffrey Aubé

  DOI：10.1021/ol047809r

  日期：2004.12.1

  The combination of the intramolecular Schmidt reaction with the Diels-Alder reaction provides expedient access to a variety of heterocycles. Two different modes of reaction planning are presented. In one, the azide and ketone moieties necessary for the intramolecular Schmidt reaction originate on different molecules that are reacted and subsequently undergo a ring-adjustment step. Alternatively, an azido ketone can be used provided the ketone is deactivated by its presence in an enone.