3-acetyl-1-(4-bromophenyl)-2-methyl-4-oxa-1-azacyclopenta[a]naphthalen-5-one | 1334474-21-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-acetyl-1-(4-bromophenyl)-2-methyl-4-oxa-1-azacyclopenta[a]naphthalen-5-one
• 英文别名: 3-Acetyl-1-(4-bromophenyl)-2-methylisochromeno[4,3-b]pyrrol-5-one；3-acetyl-1-(4-bromophenyl)-2-methylisochromeno[4,3-b]pyrrol-5-one
• CAS: 1334474-21-3
• 化学式: C₂₀H₁₄BrNO₃
• 分子量: 396.24
• InChiKey: DZXRSWICZBCWCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(4-bromophenylamino)-3-penten-2-one 在 硫酸 、 溶剂黄146 作用下， 反应 0.6h， 生成 3-acetyl-1-(4-bromophenyl)-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

文献信息

• Silica sulfuric acid: a reusable solid catalyst for one pot synthesis of densely substituted pyrrole-fused isocoumarins under solvent-free conditions
  作者：Sudipta Pathak、Kamalesh Debnath、Animesh Pramanik

  DOI：10.3762/bjoc.9.269

  日期：——

  A convenient and efficient methodology for the synthesis of densely substituted pyrrole-fused isocoumarins, which employs solid-supported silica sulfuric acid (SSA) as catalyst, has been developed. When the mixture of ninhydrin adducts of acetylacetone/ethyl acetoacetate and primary amines was heated on the solid surface of SSA under solvent-free conditions, the pyrrole-fused isocoumarins were formed

  已经开发了一种方便有效的方法，用于合成密集取代的吡咯稠合异香豆素，该方法采用固体负载二氧化硅硫酸 (SSA) 作为催化剂。当乙酰丙酮/乙酰乙酸乙酯和伯胺的茚三酮加合物混合物在无溶剂条件下在 SSA 的固体表面加热时，吡咯稠合的异香豆素以良好的产率形成。这种合成方法有几个优点，如采用无溶剂反应条件，不使用任何有毒试剂和金属催化剂，易于产品分离，使用可回收催化剂，成本低，起始原料容易获得。材料，以及优良的产品产量。
• 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.