12-methoxy-14,14-dimethyl-2,8-bis(phenylsulfonyl)tricyclo[9.4.0.03,7]pentadeca-1⁽¹¹⁾,2,6-trien-5-one

Base Information

• Chemical Name: 12-methoxy-14,14-dimethyl-2,8-bis(phenylsulfonyl)tricyclo[9.4.0.03,7]pentadeca-1⁽¹¹⁾,2,6-trien-5-one
• CAS No.: 1418184-19-6
• Molecular Formula: C₃₀H₃₂O₆S₂
• Molecular Weight: 552.712

Synonyms:12-methoxy-14,14-dimethyl-2,8-bis(phenylsulfonyl)tricyclo[9.4.0.03,7]pentadeca-1⁽¹¹⁾,2,6-trien-5-one

Chemical Property of 12-methoxy-14,14-dimethyl-2,8-bis(phenylsulfonyl)tricyclo[9.4.0.03,7]pentadeca-1⁽¹¹⁾,2,6-trien-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 12-methoxy-14,14-dimethyl-2,8-bis(phenylsulfonyl)tricyclo[9.4.0.03,7]pentadeca-1⁽¹¹⁾,2,6-trien-5-one

There total 6 articles about 12-methoxy-14,14-dimethyl-2,8-bis(phenylsulfonyl)tricyclo[9.4.0.03,7]pentadeca-1⁽¹¹⁾,2,6-trien-5-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: 18.0%

carbon monoxide (201230-82-2) + 3-methoxy-5,5,-dimethyl-2-(3-phenylsulfonylpenta-3,4-dienyl)-1-(1-phenylsulfonylpropa-1,2-dienyl)cyclohex-1-ene (1418184-18-5) → 12-methoxy-14,14-dimethyl-2,8-bis(phenylsulfonyl)tricyclo[9.4.0.03,7]pentadeca-1(11),2,6-trien-5-one (1418184-19-6)

Guidance literature:

With [RhCl(CO)dppp]₂; In toluene; for 1h; Reflux; Inert atmosphere;

DOI:10.1016/j.tet.2012.12.014

Reference yield:

2-allyl-3-hydroxy-5,5-dimethylcyclohex-1-enyl trifluoromethanesulfonate (1418184-10-7) → 12-methoxy-14,14-dimethyl-2,8-bis(phenylsulfonyl)tricyclo[9.4.0.03,7]pentadeca-1(11),2,6-trien-5-one (1418184-19-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

1.2: 1.5 h / 0 - 20 °C / Inert atmosphere

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 3.5 h / 20 °C / Inert atmosphere

2.2: Ohira-Bestmann reagent / 20 °C / Inert atmosphere

3.1: ethylmagnesium bromide / tetrahydrofuran / 2 h / 0 - 50 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

4.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere

6.1: silver(l) oxide / diethyl ether / 50 °C / Molecular sieve; Inert atmosphere

7.1: potassium carbonate / methanol / 0.17 h / Inert atmosphere

8.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / dimethyl sulfoxide / 20 °C / Inert atmosphere

9.1: triethylamine / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

9.2: 1 h / 0 °C

10.1: [RhCl(CO)dppp]₂ / toluene / 1 h / Reflux; Inert atmosphere

With 1H-imidazole; dmap; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; [RhCl(CO)dppp]₂; ethylmagnesium bromide; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; triethylamine; silver(l) oxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 8.1: |Sonogashira Cross-Coupling / 10.1: |Pauson-Khand Annulation;

DOI:10.1016/j.tet.2012.12.014

Reference yield:

3-(tert-butyldimethylsilyloxy)-2-(5-hydroxypent-3-ynyl)-5,5-dimethylcyclohex-1-enyl trifluoromethanesulfonate (1418184-13-0) → 12-methoxy-14,14-dimethyl-2,8-bis(phenylsulfonyl)tricyclo[9.4.0.03,7]pentadeca-1(11),2,6-trien-5-one (1418184-19-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere

3.1: silver(l) oxide / diethyl ether / 50 °C / Molecular sieve; Inert atmosphere

4.1: potassium carbonate / methanol / 0.17 h / Inert atmosphere

5.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / dimethyl sulfoxide / 20 °C / Inert atmosphere

6.1: triethylamine / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

6.2: 1 h / 0 °C

7.1: [RhCl(CO)dppp]₂ / toluene / 1 h / Reflux; Inert atmosphere

With dmap; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; [RhCl(CO)dppp]₂; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; triethylamine; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene; 5.1: |Sonogashira Cross-Coupling / 7.1: |Pauson-Khand Annulation;

DOI:10.1016/j.tet.2012.12.014

upstream raw materials:

2-allyl-3-hydroxy-5,5-dimethylcyclohex-1-enyl trifluoromethanesulfonate

3-(tert-butyldimethylsilyloxy)-2-(5-hydroxypent-3-ynyl)-5,5-dimethylcyclohex-1-enyl trifluoromethanesulfonate

5-[2-(3-hydroxyprop-1-ynyl)-6-methoxy-4,4-dimethylcyclohex-1-enyl]pent-2-yn-1-ol

benzenesulfenyl chloride

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