(S)-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone

Base Information

Chemical Name:(S)-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone
CAS No.:1439558-52-7
Molecular Formula:C₂₂H₂₁NO₂
Molecular Weight:331.414
Hs Code.:

Synonyms:(S)-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone

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Chemical Property of (S)-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone

Chemical Property:

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Technology Process of (S)-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone

There total 9 articles about (S)-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone 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:

: rac-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-4-(pyridin-2-ylmethyl)cyclopentane-1,3-dione

: 1439558-52-7
(S)-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone

: 1439558-44-7
(R)-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone

Guidance literature:: With (s,s) WhelkO₁ - 5 micron - 21 mm x 250mm HPLC column (chiral stationary phase - (S,S)-1-(3,5-dinitrobenzamido)-1,2,3,4-tetrahydrophenanthrene); In 2-Methylpentane; acetic acid; isopropyl alcohol; acetonitrile; Resolution of racemate;

Reference yield:

: 1237529-42-8
2-(4-bromo-2,6-dimethylphenyl)cyclopent-4-ene-1,3-dione

: 1439558-52-7
(S)-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone

: 1439558-44-7
(R)-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone

Guidance literature:: Multi-step reaction with 9 steps

1.1: acetic acid; zinc / 2 h / 90 °C

2.1: potassium carbonate / acetone / 16 h / 25 - 30 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.67 h / -75 °C / Inert atmosphere

3.2: 4.33 h / -75 - 20 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 0 - 20 °C

5.1: potassium carbonate / methanol / 25 - 30 °C

6.1: acetic acid; zinc / 25 - 30 °C

7.1: bis-triphenylphosphine-palladium(II) chloride; 1,4-di(diphenylphosphino)-butane; tetrabutyl ammonium fluoride / tetrahydrofuran; dimethyl sulfoxide / 0.67 h / 110 °C / Inert atmosphere

8.1: hydrogenchloride / acetone; water / 0.67 h / 80 °C / Microwave irradiation

9.1: (s,s) WhelkO₁ - 5 micron - 21 mm x 250mm HPLC column (chiral stationary phase - (S,S)-1-(3,5-dinitrobenzamido)-1,2,3,4-tetrahydrophenanthrene) / 2-Methylpentane; isopropyl alcohol; acetonitrile; acetic acid / Resolution of racemate

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; triethylamine; 1,4-di(diphenylphosphino)-butane; lithium hexamethyldisilazane; zinc; In tetrahydrofuran; methanol; 2-Methylpentane; dichloromethane; water; acetic acid; dimethyl sulfoxide; isopropyl alcohol; acetone; acetonitrile;

Reference yield:

: 2-(4-bromo-2,6-dimethylphenyl)-5-(hydroxypyridin-2-ylmethyl)-3-methoxycyclopent-2-enone

: 1439558-52-7
(S)-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone

: 1439558-44-7
(R)-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone

Guidance literature:: Multi-step reaction with 6 steps

1: triethylamine / dichloromethane / 0 - 20 °C

2: potassium carbonate / methanol / 25 - 30 °C

3: acetic acid; zinc / 25 - 30 °C

4: bis-triphenylphosphine-palladium(II) chloride; 1,4-di(diphenylphosphino)-butane; tetrabutyl ammonium fluoride / tetrahydrofuran; dimethyl sulfoxide / 0.67 h / 110 °C / Inert atmosphere

5: hydrogenchloride / acetone; water / 0.67 h / 80 °C / Microwave irradiation

6: (s,s) WhelkO₁ - 5 micron - 21 mm x 250mm HPLC column (chiral stationary phase - (S,S)-1-(3,5-dinitrobenzamido)-1,2,3,4-tetrahydrophenanthrene) / 2-Methylpentane; isopropyl alcohol; acetonitrile; acetic acid / Resolution of racemate

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; triethylamine; 1,4-di(diphenylphosphino)-butane; zinc; In tetrahydrofuran; methanol; 2-Methylpentane; dichloromethane; water; acetic acid; dimethyl sulfoxide; isopropyl alcohol; acetone; acetonitrile;