(3aS,4aS,10bR)-3,3a,4,4a-tetrahydrothieno[3',4':2,3]cyclobuta[1,2-c]chromen-5(1H)-one

Base Information

Chemical Name:(3aS,4aS,10bR)-3,3a,4,4a-tetrahydrothieno[3',4':2,3]cyclobuta[1,2-c]chromen-5(1H)-one
CAS No.:1392100-89-8
Molecular Formula:C₁₃H₁₂O₂S
Molecular Weight:232.303
Hs Code.:

Synonyms:(3aS,4aS,10bR)-3,3a,4,4a-tetrahydrothieno[3',4':2,3]cyclobuta[1,2-c]chromen-5(1H)-one

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Chemical Property of (3aS,4aS,10bR)-3,3a,4,4a-tetrahydrothieno[3',4':2,3]cyclobuta[1,2-c]chromen-5(1H)-one

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Technology Process of (3aS,4aS,10bR)-3,3a,4,4a-tetrahydrothieno[3',4':2,3]cyclobuta[1,2-c]chromen-5(1H)-one

There total 5 articles about (3aS,4aS,10bR)-3,3a,4,4a-tetrahydrothieno[3',4':2,3]cyclobuta[1,2-c]chromen-5(1H)-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: 26.0%

: 1392001-52-3
4-(allylthiomethyl)coumarin

: 607-71-6
4-methyl-2H-chromen-2-one

: (3aR,4aR,10bS)-3,3a,4,4a-tetrahydrothieno[3',4':2,3]cyclobuta[1,2-c]chromen-5(1H)-one

: 1392100-89-8
(3aS,4aS,10bR)-3,3a,4,4a-tetrahydrothieno[3',4':2,3]cyclobuta[1,2-c]chromen-5(1H)-one

Guidance literature:: With ((3aS)-3,3-bis(3,5-dimethylphenyl)-1-(2-(trifluoromethyl)phenyl)hexahydro-1H-pyrrolo[1,2-c][1,3,2]oxazaborol-7-ium-7-yl)tribromoaluminate; In dichloromethane; at -75 ℃; for 5.5h; optical yield given as %ee; stereoselective reaction; Inert atmosphere; Irradiation;
DOI:10.1002/chem.201104032

Reference yield:

: C₁₁H₁₀O₅S

: 607-71-6
4-methyl-2H-chromen-2-one

: (3aR,4aR,10bS)-3,3a,4,4a-tetrahydrothieno[3',4':2,3]cyclobuta[1,2-c]chromen-5(1H)-one

: 1392100-89-8
(3aS,4aS,10bR)-3,3a,4,4a-tetrahydrothieno[3',4':2,3]cyclobuta[1,2-c]chromen-5(1H)-one

Guidance literature:: Multi-step reaction with 3 steps

1: lithium bromide / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

2: triethylamine / N,N-dimethyl-formamide / 9 h / 20 °C

3: ((3aS)-3,3-bis(3,5-dimethylphenyl)-1-(2-(trifluoromethyl)phenyl)hexahydro-1H-pyrrolo[1,2-c][1,3,2]oxazaborol-7-ium-7-yl)tribromoaluminate / dichloromethane / 5.5 h / -75 °C / Inert atmosphere; Irradiation

With ((3aS)-3,3-bis(3,5-dimethylphenyl)-1-(2-(trifluoromethyl)phenyl)hexahydro-1H-pyrrolo[1,2-c][1,3,2]oxazaborol-7-ium-7-yl)tribromoaluminate; triethylamine; lithium bromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/chem.201104032

Reference yield:

: 82156-55-6
4-bromomethyl-2H-chromen-2-one

: 607-71-6
4-methyl-2H-chromen-2-one

: (3aR,4aR,10bS)-3,3a,4,4a-tetrahydrothieno[3',4':2,3]cyclobuta[1,2-c]chromen-5(1H)-one

: 1392100-89-8
(3aS,4aS,10bR)-3,3a,4,4a-tetrahydrothieno[3',4':2,3]cyclobuta[1,2-c]chromen-5(1H)-one

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine / N,N-dimethyl-formamide / 9 h / 20 °C

2: ((3aS)-3,3-bis(3,5-dimethylphenyl)-1-(2-(trifluoromethyl)phenyl)hexahydro-1H-pyrrolo[1,2-c][1,3,2]oxazaborol-7-ium-7-yl)tribromoaluminate / dichloromethane / 5.5 h / -75 °C / Inert atmosphere; Irradiation

With ((3aS)-3,3-bis(3,5-dimethylphenyl)-1-(2-(trifluoromethyl)phenyl)hexahydro-1H-pyrrolo[1,2-c][1,3,2]oxazaborol-7-ium-7-yl)tribromoaluminate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/chem.201104032