4354-74-9

Usage

Parent compound

2(3H)-Furanone, a heterocyclic organic compound with a furan ring.

Derivative

3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl] substituent, which modifies the parent furanone structure.

Ethyl group

A C2H5 alkyl group attached to the molecule, contributing to its structure and properties.

Dihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl] substituent

A complex functional group that includes an imidazole ring, contributing to the compound's potential biological activity.

Imidazole group

A five-membered heterocyclic ring with two nitrogen atoms, which is found in many bioactive molecules and pharmaceuticals.

Pleasant aroma

Furanones are known for their pleasant aroma, making them suitable for use in the fragrance industry.

Taste-enhancing properties

Furanones can enhance the taste of food products, making them useful in the food industry.

Potential biological activity

The presence of the imidazole group suggests that 2(3H)-Furanone, 3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]- may have biological activity, which requires further research and testing.

Specific properties and uses

The properties and potential applications of 2(3H)-Furanone, 3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]- would depend on further research and testing, as it is a derivative of furanone with specific substituents.

Upstream product

• 127-67-3 (+/-)-pilocarpidine 
• 74-88-4 methyl iodide 
• 35594-22-0 3r-ethyl-4c-(3-methyl-2-thioxo-2,3-dihydro-1H-imidazol-4-ylmethyl)-dihydro-furan-2-one 
• 127-67-3 (+/-)-isopilocarpidine 
• 7647-01-0 hydrogenchloride 
• 34350-99-7 Isopilocarpinsaeure 
• 64-17-5 ethanol 
• 92-13-7 pilocarpine 
• 62-53-3 aniline 
• 71-41-0 pentan-1-ol 
• 64-19-7 acetic acid 
• 54-71-7 pilocarpine hydrochloride 
• 1171129-17-1 (RS,E)-3-ethylidene-4-[(1-methylimidazol-5-yl)methyl]tetrahydrofuran-2-one 
• 35594-22-0 (+/-)-trans-3-ethyl-4-(3-methyl-2-thioxo-2,3-dihydro-1H-imidazol-4-ylmethyl)-dihydro-furan-2-one 

Downstream Products

• 92-13-7 pilocarpine 
• 5984-67-8 4-((3R)-4-ethyl-5-oxo-tetrahydro-furan-3t-ylmethyl)-1,3-dimethyl-imidazolium; iodide 
• 34350-99-7 Isopilocarpinsaeure 

Relevant academic research and scientific papers

Syntheses of the racemic jaborandi alkaloids pilocarpine, isopilocarpine and pilosinine

The synthesis of racemic pilocarpine has been achieved in high overall yield. Two alternative approaches for the formation of the γ-butyrolactone ring are described: the first involves a palladium-catalysed carbonylation reaction of a homopropargylic alco

A practical and scaleable total synthesis of the jaborandi alkaloid (+)-pilocarpine

The total synthesis of (+)-pilocarpine (as its nitrate salt) has been achieved in nine steps and 30% overall yield starting from racemic 2-(2′,2′-dimethoxyethyl)propane-1,3-diol, which was desymmetrised via an enzymatic protocol. A high yielding synthesis of a key α-ethylidene lactone precursor has been developed, which involves the palladium-catalysed decarboxylation/carbonylation of a 1,3-dioxan-2-one for formation of the γ-butyrolactone ring. Subsequent hydrogenation of the α-ethylidene lactone introduces the C(3)-stereochemistry to give a 72:28 mixture of (+)-pilocarpine and (+)-isopilocarpine, which are readily separable via recrystallisation of the (+)-pilocarpine nitrate salt.

Convergent diastereoselective synthesis of isopilocarpine by one-pot Michael-addition-alkylation reaction

The metalated dithiane 7b available from imidazole aldehyde 6 is reacted with furanone 4 and ethyl iodide to give the lactone 8, which forms diastereoselectively. Its configuration is determined to be trans by means of a crystal structure analysis. The desulfurization of 8 leads to the alkaloid isopilocarpine 2 in three steps and 25% overall yield. The relative energies of the diastereomeric alkaloids 1 and 2 have been calculated.