2-(N,N-diallylamino)-acetophenone | 748771-57-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(N,N-diallylamino)-acetophenone
• 英文别名: 1-[2-[Bis(prop-2-enyl)amino]phenyl]ethanone
• CAS: 748771-57-5
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: QRMIDAUFURWXLF-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：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2'-氟苯乙酮 、 二烯丙基胺 生成 2-(N,N-diallylamino)-acetophenone
  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

• Design, synthesis, and evaluation of bromo-retrochalcone derivatives as protein tyrosine phosphatase 1B inhibitors
  作者：Zhiguo Liu、Woojung Lee、Su-Nam Kim、Goo Yoon、Seung Hoon Cheon

  DOI：10.1016/j.bmcl.2011.04.057

  日期：2011.6

  A series of bromo-retrochalcones was designed, synthesized and evaluated as PTP1B inhibitors based on licochalcone A and E. Compounds 6, 12, 13, 14, 25, 36, 37, 39, and 41 showed potent inhibitory effects against PTP1B, and compound 37, the most potent among the series, had an IC(50) value of 1.9 mu M, about two-fold better than that of the positive control, ursolic acid. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.