84186-26-5

Basic information

• Product Name: 1H-Naphtho[2,1-b]pyran-2-carboxylic acid, 3-amino-1-phenyl-, ethyl ester
• Synonyms: ethyl 3-amino-1-phenyl-1H-benzo[f]chromene-2-carboxylate
• CAS NO: 84186-26-5
• Molecular Formula: C22H19NO3
• Molecular Weight: 345.398
• Mol File: 84186-26-5.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: 1H-Naphtho[2,1-b]pyran-2-carboxylic acid, 3-amino-1-phenyl-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Naphtho[2,1-b]pyran-2-carboxylic acid, 3-amino-1-phenyl-, ethyl ester(84186-26-5)
• EPA Substance Registry System: 1H-Naphtho[2,1-b]pyran-2-carboxylic acid, 3-amino-1-phenyl-, ethyl ester(84186-26-5)

Safety Data

• Hazardous Substances Data: 84186-26-5(Hazardous Substances Data)

Upstream product

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• 135-19-3 β-naphthol 
• 64992-15-0 C₈H₁₅N₂O₂⁽¹⁺⁾*Cl^(1-) 
• 64-17-5 ethanol 
• 1277100-30-7 C₂₅H₂₇N₂O₃⁽¹⁺⁾*Cl^(1-) 
• 100-52-7 benzaldehyde 
• 105-56-6 ethyl 2-cyanoacetate 
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Relevant articles and documents

Synthesis and biological evaluation of benzochromenopyrimidinones as cholinesterase inhibitors and potent antioxidant, non-hepatotoxic agents for Alzheimer's disease

We report herein the straightforward two-step synthesis and biological assessment of novel racemic benzochromenopyrimidinones as non-hepatotoxic, acetylcholinesterase inhibitors with antioxidative properties. Among them, compound 3Bb displayed a mixed-type inhibition of human acetylcholinesterase (IC50 = 1.28 ± 0.03 μM), good antioxidant activity, and also proved to be non-hepatotoxic on human HepG2 cell line.

Aqua one-pot, three-component synthesis of dihydropyrano[3,2-c]chromenes and amino-benzochromenes catalyzed by sodium malonate

The widespread biological properties of dihydropyrano[3,2-c]chromenes, 2-amino-4-aryl-4H-benzo[h]chromenes, and 3-amino-1-aryl-1H-benzo[f]chromenes have led to increasing efforts for the development of tremendously effective synthetic protocols aimed at their synthesis. In this contribution, sodium malonate was employed for the first time as an efficient catalyst for the one-pot, three-component tandem Knoevenagel–cyclocondensation reaction of 4-hydroxycoumarin (or naphthols), malononitrile/ethyl cyanoacetate, and various aldehydes. These compounds underwent Knoevenagel–Michael–Thorpe–Ziegler cyclization upon heating at 70?°C in water to give the respective medicinally relevant dihydropyrano[3,2-c]chromenes and amino-benzochromenes. The method is versatile and amenable to many substrates as it requires no specialized devices such as microwave, ultrasound and ball-milling. Also, the salient features of this high-yielding protocol are green reaction conditions, the use of commercially available catalyst, easy purification processes by a simple filtration, and relatively shorter reaction times.

Potassium phthalimide-catalysed one-pot multi-component reaction for efficient synthesis of amino-benzochromenes in aqueous media

2-Amino-4-aryl-4H-benzo[h]chromenes and 3-amino-1-aryl-1H-benzo[f]chromenes were prepared by treating cyano-methylene compounds (malononitrile or ethyl cyanoacetate), substituted aromatic aldehydes, and naphtholic compounds in the presence of potassium phthalimide as a green, mild, efficient, and commercially available organocatalyst in aqueous media. The procedure was readily conducted and affords remarkable advantages such as safety, short reaction times, environmentally benign milder reaction conditions, no organic solvent required, and high yields.