244056-98-2

Basic information

• Product Name: (3aS*,7aS*)-Benzyl 2-(bromomethyl)hexahydrofuro[3,2-β]pyridine -4(2H)-carboxylate
• Synonyms: (3aR,7aR)-rel-2-(Bromomethyl)hexahydro-furo[3,2-β]pyridine-4(2H)-carboxylic Acid Phenylmethyl Ester;(3aS*,7aS*)-Benzyl 2-(bromomethyl)hexahydrofuro[3,2-β]pyridine -4(2H)-carboxylate;(3aR,7aR)-rel-2-(Bromomethyl)hexahydro-furo[3,2-b]pyridine-4(2H)-carboxylic Acid Phenylmethyl Ester;(3aS*,7aS*)-Benzyl 2-(bromomethyl)hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate;(3aS*,7aS*)-Benzyl 2-(bromomethyl)hexahydrofuro[3,2-b]pyridine\n-4(2H)-carboxylate
• CAS NO: 244056-98-2
• Molecular Formula: C16H20BrNO3
• Molecular Weight: 354.242
• Product Categories: Aromatics Compounds;Aromatics;Chiral Reagents;Heterocycles
• Mol File: 244056-98-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 460.038°C at 760 mmHg
• Flash Point: 232.023°C
• Appearance: /
• Density: 1.387g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.567
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• PKA: -1.35±0.40(Predicted)
• CAS DataBase Reference: (3aS*,7aS*)-Benzyl 2-(bromomethyl)hexahydrofuro[3,2-β]pyridine -4(2H)-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (3aS*,7aS*)-Benzyl 2-(bromomethyl)hexahydrofuro[3,2-β]pyridine -4(2H)-carboxylate(244056-98-2)
• EPA Substance Registry System: (3aS*,7aS*)-Benzyl 2-(bromomethyl)hexahydrofuro[3,2-β]pyridine -4(2H)-carboxylate(244056-98-2)

Safety Data

• Hazardous Substances Data: 244056-98-2(Hazardous Substances Data)

Usage

Chemical Properties

Light Yellow Oil

InChI:InChI=1/C16H20BrNO3/c17-10-13-9-14-15(21-13)7-4-8-18(14)16(19)20-11-12-5-2-1-3-6-12/h1-3,5-6,13-15H,4,7-11H2/t13?,14-,15-/m0/s1

Upstream product

• 109-00-2 3-HYDROXYPYRIDINE 
• 304436-21-3 benzyl (R)-2-allyl-3-oxopiperidine-1-carboxylate 
• 244056-97-1 Benzyl 2-allyl-3-oxo-1-piperidinecarboxylate 
• 304436-17-7 benzyl (2S,3S)-2-allyl-3-hydroxypiperidine-1-carboxylate 
• 100-44-7 benzyl chloride 
• 244056-96-0 benzyl 1-(3-allyloxy-1,2,5,6-tetrahydropyridine)carboxylate 
• 244056-95-9 5-(Allyloxy)-1-benzyl-1,2,3,6-tetrahydropyridine 
• 3323-73-7 1-Benzyl-3-hydroxypyridinium chloride 
• 244056-94-8 (2S*,3S*)-Benzyl 2-allyl-3-hydroxy-1-piperidinecarboxylate 

Downstream Products

• 32434-44-9 (+)-isofebrifugine 
• 24159-07-7 dl-febrifugine 
• 7312-34-7 5-methyl-2,3-dihydro-1H-pyrrolizine 
• 24159-07-7 febrifugine 

Relevant articles and documents

Synthesis and biological evaluation of isofebrifugine analogues

Isofebrifugine, as a kind of natural quinazolinone alkaloid with important physiological activities and good pharmacological effects, was isolated from a Chinese medicinal plant, Chang Shan (Dichroa febrifuga). In this paper, the synthesis of a series of novel isofebrifugine analogues was accomplished by employing the N-alkylation of 4(3H)-quinazolinones with benzyl (3aR,7aR)-rel-2-(bromomethyl)hexahydrofuro[3,2-b]pyridine-4(2H)carboxylates and the subsequent N-deprotection. These analogues were characterized by1 H NMR,13 C NMR and HRMS spectra. The MTT assay was used to examine the inhibitory effects of these analogues on the growth of human hepatoma cells (HepG2). The results indicated that some halogenated or hemiketal analogues showed interesting inhibition activity.

Asymmetric synthesis of (+)-febrifugine and (+)-isofebrifugine using yeast reduction

The antimalarial agents febrifugine (D-1) and isofebrifugine (D-2) were synthesized from chiral 3-piperidinol (D-4), which was asymmetrically prepared by the yeast reduction of 3-piperidone derivatives (DL-3), with dynamic optical resolution.

Synthesis of D/L-febrifugine and D/L-isofebrifugine

Racemic compounds (1 and 2) of the antimalarial agents febrifugine (D-1) and isofebrifugine (D-2) were synthesized using an unusual Claisen rearrangement of allyl enol ether 6 and the stereoselective reduction of 2- allylpiperid-3-one 8. This method is widely applicable to the synthesis of febirifugine derivatives.