(3R)-3-(but-3-enyl)-3-(4-(tetrahydro-2H-pyran-2-yloxy)but-1-ynyl)cyclohexanone

Base Information

Chemical Name:(3R)-3-(but-3-enyl)-3-(4-(tetrahydro-2H-pyran-2-yloxy)but-1-ynyl)cyclohexanone
CAS No.:1270183-46-4
Molecular Formula:C₁₉H₂₈O₃
Molecular Weight:304.43
Hs Code.:

Synonyms:(3R)-3-(but-3-enyl)-3-(4-(tetrahydro-2H-pyran-2-yloxy)but-1-ynyl)cyclohexanone

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3R)-3-(but-3-enyl)-3-(4-(tetrahydro-2H-pyran-2-yloxy)but-1-ynyl)cyclohexanone

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Technology Process of (3R)-3-(but-3-enyl)-3-(4-(tetrahydro-2H-pyran-2-yloxy)but-1-ynyl)cyclohexanone

There total 4 articles about (3R)-3-(but-3-enyl)-3-(4-(tetrahydro-2H-pyran-2-yloxy)but-1-ynyl)cyclohexanone 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%

: 1270183-14-6
3-(4-(tetrahydro-2H-pyran-2-yloxy)but-1-ynyl)cyclohex-2-enone

: 7103-09-5
4-but-1-enylmagnesium bromide

: 1270183-46-4
(3R)-3-(but-3-enyl)-3-(4-(tetrahydro-2H-pyran-2-yloxy)but-1-ynyl)cyclohexanone

Guidance literature:: With C₁₈H₂₉N₂O⁽¹⁺⁾*Cl^(1-); copper(II) bis(trifluoromethanesulfonate); In dichloromethane; at -10 ℃; for 1.25h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
DOI:10.1021/ol200219m

Reference yield:

: C₁₅H₂₂O₃

: 1270183-46-4
(3R)-3-(but-3-enyl)-3-(4-(tetrahydro-2H-pyran-2-yloxy)but-1-ynyl)cyclohexanone

Guidance literature:: Multi-step reaction with 2 steps

1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; silica-supported sodium periodate / dichloromethane / 20 °C / Inert atmosphere

2: C₁₈H₂₉N₂O⁽¹⁺⁾*Cl^(1-); copper(II) bis(trifluoromethanesulfonate) / dichloromethane / 1.25 h / -10 °C / Inert atmosphere

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; silica-supported sodium periodate; C₁₈H₂₉N₂O⁽¹⁺⁾*Cl^(1-); copper(II) bis(trifluoromethanesulfonate); In dichloromethane;
DOI:10.1021/ol200219m

Reference yield:

: 40365-61-5
2-(but-3-yn-1-yloxy)tetrahydropyran

: 1270183-46-4
(3R)-3-(but-3-enyl)-3-(4-(tetrahydro-2H-pyran-2-yloxy)but-1-ynyl)cyclohexanone

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran / 1 h / Cooling; Inert atmosphere

1.2: 1.08 h / -78 °C / Inert atmosphere

2.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; silica-supported sodium periodate / dichloromethane / 20 °C / Inert atmosphere

3.1: C₁₈H₂₉N₂O⁽¹⁺⁾*Cl^(1-); copper(II) bis(trifluoromethanesulfonate) / dichloromethane / 1.25 h / -10 °C / Inert atmosphere

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; n-butyllithium; silica-supported sodium periodate; C₁₈H₂₉N₂O⁽¹⁺⁾*Cl^(1-); copper(II) bis(trifluoromethanesulfonate); In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol200219m