3-acetyl-1-(4-chlorophenyl)-2-methyl-4-oxa-1-azacyclopenta[a]naphthalen-5-one | 1334474-17-7

• 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-chlorophenyl)-2-methyl-4-oxa-1-azacyclopenta[a]naphthalen-5-one
• 英文别名: 3-Acetyl-1-(4-chlorophenyl)-2-methylisochromeno[4,3-b]pyrrol-5-one；3-acetyl-1-(4-chlorophenyl)-2-methylisochromeno[4,3-b]pyrrol-5-one
• CAS: 1334474-17-7
• 化学式: C₂₀H₁₄ClNO₃
• 分子量: 351.789
• InChiKey: GEYVCUWSIQOFEU-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-chlorophenylamino)pent-3-en-2-one 在 硫酸 、 溶剂黄146 作用下， 反应 0.62h， 生成 3-acetyl-1-(4-chlorophenyl)-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。
• Environment dependent photophysical and fluorescence turn-off sensing properties of Fe(III) by substituted phenyl isochromenopyrrol-5-ones
  作者：A. Roniboss、Milind Shrinivas Dangate、R. Nishanth Rao、M M Balamurali、Kaushik Chanda

  DOI：10.1039/c9pp00303g

  日期：2019.12

  Montomorillonite K10 as a catalyst and characterized. The electronic structure and geometry of all the synthesized compounds were investigated experimentally by UV-visible absorption and fluorescence spectroscopy. A negligible shift was observed in the absorption spectrum while a large red shift was observed in the fluorescence spectrum upon changing from non-polar to polar solvents. The experimental results

  以蒙脱石K10为催化剂合成了异色吡咯烷酮的类似物并进行了表征。通过紫外-可见吸收和荧光光谱实验研究了所有合成化合物的电子结构和几何形状。从非极性溶剂变为极性溶剂后，在吸收光谱中观察到的偏移可忽略不计，而在荧光光谱中观察到大的红移。将实验结果与密度泛函理论计算的结果进行了比较。所观察到的光物理性质是由溶剂环境引起的。除氯取代外，其他官能团（如甲基，二甲基，二乙基或甲氧基）不会显着影响分子的电子性能。实验结果与理论解释相吻合。此外，这些异色吡咯烷酮对Fe（III）离子通过荧光关闭机制检测极限为〜10 -6 M且缔合常数为〜10 3 M -1。建议这些分子可以在环境传感应用中找到其用途。