6-(but-3-enyl)-4-(phenylthio)-1-(4-toluenesulfonyl)-1,2,5,6-tetrahydropyridin-2-one

Base Information

• Chemical Name: 6-(but-3-enyl)-4-(phenylthio)-1-(4-toluenesulfonyl)-1,2,5,6-tetrahydropyridin-2-one
• CAS No.: 597556-90-6
• Molecular Formula: C₂₂H₂₃NO₃S₂
• Molecular Weight: 413.562
• Mol file: 597556-90-6.mol

Synonyms:6-(but-3-enyl)-4-(phenylthio)-1-(4-toluenesulfonyl)-1,2,5,6-tetrahydropyridin-2-one

Chemical Property of 6-(but-3-enyl)-4-(phenylthio)-1-(4-toluenesulfonyl)-1,2,5,6-tetrahydropyridin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(but-3-enyl)-4-(phenylthio)-1-(4-toluenesulfonyl)-1,2,5,6-tetrahydropyridin-2-one

There total 2 articles about 6-(but-3-enyl)-4-(phenylthio)-1-(4-toluenesulfonyl)-1,2,5,6-tetrahydropyridin-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

Tosyl isocyanate (4083-64-1) + 2-But-3-enyl-4-phenylsulfanyl-2,5-dihydro-thiophene 1,1-dioxide (197862-42-3) → 6-(but-3-enyl)-4-(phenylthio)-1-(4-toluenesulfonyl)-1,2,5,6-tetrahydropyridin-2-one (597556-90-6)

Guidance literature:

With sodium hydrogencarbonate; hydroquinone; In toluene; at 110 ℃; for 4.5h;

DOI:10.1016/S0040-4039(03)01096-7 DOI:10.1016/j.tet.2007.05.104

Reference yield:

3-thiophenyl-3-sulfolene (64741-13-5) → 6-(but-3-enyl)-4-(phenylthio)-1-(4-toluenesulfonyl)-1,2,5,6-tetrahydropyridin-2-one (597556-90-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BuLi; HMPA / tetrahydrofuran / -105 °C

1.2: 74 percent / tetrahydrofuran / -90 - -50 °C

2.1: 79 percent / NaHCO₃; hydroquinone / toluene / 4.5 h / 110 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; sodium hydrogencarbonate; hydroquinone; In tetrahydrofuran; toluene; 2.1: aza-Diels-Alder reaction;

DOI:10.1016/j.tet.2007.05.104

Reference yield: 91.0%

acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) + 6-(but-3-enyl)-4-(phenylthio)-1-(4-toluenesulfonyl)-1,2,5,6-tetrahydropyridin-2-one (597556-90-6) → 6-(E)-[4-(methoxycarbonyl)but-3-enyl]-4-(phenylthio)-1-tosyl-1,2,5,6-tetrahydro-2-pyridinone (1401207-51-9)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; p-cresol; In toluene; at 150 ℃; for 0.5h; Microwave irradiation;

DOI:10.1016/j.tetlet.2012.08.031

upstream raw materials:

Tosyl isocyanate

2-But-3-enyl-4-phenylsulfanyl-2,5-dihydro-thiophene 1,1-dioxide

3-thiophenyl-3-sulfolene

Downstream raw materials:

6-(but-3-enyl)-4-(phenylthio)-1,2,5,6-tetrahydropyridin-2-one

1-allyl-6-(but-3-enyl)-4-(phenylthio)-1,2,5,6-tetrahydropyridin-2-one

2-(phenylthio)-1,6,9,10,10a-pentahydropyrido[1,2-a]azepin-4-one

6-(E)-[4-(methoxycarbonyl)but-3-enyl]-4-(phenylthio)-1-tosyl-1,2,5,6-tetrahydro-2-pyridinone