3-acetyl-1-benzyl-2-methylisochromeno[4,3-b]pyrrol-5(1H)-one | 1334474-13-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: 3-acetyl-1-benzyl-2-methylisochromeno[4,3-b]pyrrol-5(1H)-one
• 英文别名: 3-acetyl-1-benzyl-2-methyl-4-oxa-1-azacyclopenta[a]naphthalen-5-one；3-Acetyl-1-benzyl-2-methylisochromeno[4,3-b]pyrrol-5-one；3-acetyl-1-benzyl-2-methylisochromeno[4,3-b]pyrrol-5-one
• CAS: 1334474-13-3
• 化学式: C₂₁H₁₇NO₃
• 分子量: 331.371
• InChiKey: FNVQDECHTFSYFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  1-acetyl-3-benzyl-3a,8a-dihydroxy-2-methyl-3a,8a-dihydro-3-azacyclopenta[a]inden-8-one 在 硫酸 、 溶剂黄146 作用下， 反应 0.08h， 以95%的产率得到3-acetyl-1-benzyl-2-methylisochromeno[4,3-b]pyrrol-5(1H)-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。
• Fluorescent and antioxidant studies of effectively synthesized isochromenopyrrolone analogues
  作者：Hariyapureddy Raveendranatha Reddy、Chitreddy V. Subba Reddy、Radhakrishnan Subashini、Selvaraj Mohana Roopan

  DOI：10.1039/c4ra02792b

  日期：——

  strategy for the synthesis of 3-acetyl-2-methyl-1-phenylisochromeno [4,3-b] pyrrol-5(1H)-ones 4a–f have been developed using montmorillonite K10 as a catalyst. The reaction proceeded from acetyl acetone, substituted primary amines and ninhydrin via acidic media under solvent-free conditions. Compounds 4a–c exhibit green fluorescence under UV light, and their fluorescent properties in the liquid state

  使用蒙脱石K10作为催化剂，已经开发出一种有效的合成3-乙酰基-2-甲基-1-苯基异铬[4,3 - b ]吡咯-5（1 H）-ones 4a-f的策略。在无溶剂条件下，经由酸性介质，由乙酰丙酮，取代的伯胺和茚三酮进行反应。化合物4a–c在紫外光下显示绿色荧光，并研究了它们在液态时的荧光特性。对所有合成的化合物进行自由基清除活性的评估。与标准品相比，所有测试化合物4a和4c均显示出良好的抑制百分比，即抗坏血酸。
• 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.