4-(3-Hydroxyanilino)pent-3-en-2-one | 294851-90-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(3-Hydroxyanilino)pent-3-en-2-one
• CAS: 294851-90-4
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: XHLASXCUFACIRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  水合茚三酮 、 4-(3-Hydroxyanilino)pent-3-en-2-one 在 硫酸 、 溶剂黄146 作用下， 反应 0.62h， 生成 3-acetyl-1-(3-hydroxyphenyl)-2-methyl-4-oxa-1-azacyclopenta[a]naphthalen-5-one
  参考文献：
  名称：

  Facile synthesis of substituted pyrrole-fused isocoumarins from ninhydrin

  摘要：

  A simple and efficient procedure has been developed for the synthesis of substituted pyrrole-fused isocoumarins from easily available ninhydrin. The cyclic hemiaminal dihydroxy-indenopyrroles, the adducts of ninhydrin with enamines of acetylacetone, give pyrrole-fused isocournarins upon heating in acidic medium. The process constitutes an interesting acid-catalyzed rearrangement to eight-membered lactams followed by intramolecular cyclization involving the amino and keto groups. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.133
• 作为产物：
  描述：

  3-氨基苯酚 、 乙酰丙酮 反应 0.25h， 生成 4-(3-Hydroxyanilino)pent-3-en-2-one
  参考文献：
  名称：

  Facile synthesis of substituted pyrrole-fused isocoumarins from ninhydrin

  摘要：

  A simple and efficient procedure has been developed for the synthesis of substituted pyrrole-fused isocoumarins from easily available ninhydrin. The cyclic hemiaminal dihydroxy-indenopyrroles, the adducts of ninhydrin with enamines of acetylacetone, give pyrrole-fused isocournarins upon heating in acidic medium. The process constitutes an interesting acid-catalyzed rearrangement to eight-membered lactams followed by intramolecular cyclization involving the amino and keto groups. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.133

文献信息

• A Unique 1,2-Acyl Migration for the Construction of Quaternary Carbon by Visible Light Irradiation of Platinum(II) Polypyridyl Complex and Molecular Oxygen
  作者：Qing-Yuan Meng、Tao Lei、Lei-Min Zhao、Cheng-Juan Wu、Jian-Ji Zhong、Xue-Wang Gao、Chen-Ho Tung、Li-Zhu Wu

  DOI：10.1021/ol502995h

  日期：2014.11.21

  A unique 1,2-acyl migration for the construction of quaternary carbon in a one-pot reaction under visible light is described. By irradiating a platinum(II) polypyridyl complex with visible light, enamine 1 is able to react with alcohol 2 to yield compound 3 featuring a quaternary carbon via 1,2-acyl migration and concurrent esterification. Studies on the mechanism reveal that the platinum(II) complex is able to generate singlet oxygen (O-1(2)) that is responsible for this unprecedented intramolecular 1,2-acyl migration transformation.
• Facile synthesis of substituted pyrrole-fused isocoumarins from ninhydrin
  作者：Sudipta Pathak、Ashis Kundu、Animesh Pramanik

  DOI：10.1016/j.tetlet.2011.07.133

  日期：2011.10

  A simple and efficient procedure has been developed for the synthesis of substituted pyrrole-fused isocoumarins from easily available ninhydrin. The cyclic hemiaminal dihydroxy-indenopyrroles, the adducts of ninhydrin with enamines of acetylacetone, give pyrrole-fused isocournarins upon heating in acidic medium. The process constitutes an interesting acid-catalyzed rearrangement to eight-membered lactams followed by intramolecular cyclization involving the amino and keto groups. (C) 2011 Elsevier Ltd. All rights reserved.