(R)-3-[2-(5,8-Dimethoxy-naphthalen-2-yl)-ethyl]-2,2-dimethyl-4-methylene-cyclohexanone

Base Information

Chemical Name:(R)-3-[2-(5,8-Dimethoxy-naphthalen-2-yl)-ethyl]-2,2-dimethyl-4-methylene-cyclohexanone
CAS No.:866223-68-9
Molecular Formula:C₂₃H₂₈O₃
Molecular Weight:352.474
Hs Code.:

Synonyms:(R)-3-[2-(5,8-Dimethoxy-naphthalen-2-yl)-ethyl]-2,2-dimethyl-4-methylene-cyclohexanone

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Chemical Property of (R)-3-[2-(5,8-Dimethoxy-naphthalen-2-yl)-ethyl]-2,2-dimethyl-4-methylene-cyclohexanone

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Technology Process of (R)-3-[2-(5,8-Dimethoxy-naphthalen-2-yl)-ethyl]-2,2-dimethyl-4-methylene-cyclohexanone

There total 5 articles about (R)-3-[2-(5,8-Dimethoxy-naphthalen-2-yl)-ethyl]-2,2-dimethyl-4-methylene-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: 63.0%

: 866223-67-8
(1S,3R)-3-[2-(5,8-Dimethoxy-naphthalen-2-yl)-ethyl]-2,2-dimethyl-4-methylene-cyclohexanol

: 866223-68-9
(R)-3-[2-(5,8-Dimethoxy-naphthalen-2-yl)-ethyl]-2,2-dimethyl-4-methylene-cyclohexanone

Guidance literature:: With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1016/j.tet.2005.06.115

Reference yield:

: Toluene-4-sulfonic acid 2-[(1R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-6-methylene-cyclohexyl]-ethyl ester

: 866223-68-9
(R)-3-[2-(5,8-Dimethoxy-naphthalen-2-yl)-ethyl]-2,2-dimethyl-4-methylene-cyclohexanone

Guidance literature:: Multi-step reaction with 4 steps

1.1: 923 mg / NaI / acetone / 4 h / Heating

2.1: t-BuLi; 9-methoxy-9-borabicyclo[3.3.1]nonane / various solvents / 1.42 h / -78 - 20 °C

2.2: 50 percent / K₃PO₄ / [Pd(PPh₃)4] / various solvents / 16 h / 80 °C

3.1: 90 percent / TBAF / tetrahydrofuran / 6 h / 50 - 60 °C

4.1: 63 percent / PCC / CH₂Cl₂ / 0.5 h / 20 °C

With tetrabutyl ammonium fluoride; tert.-butyl lithium; 9-methoxy-9-BBN; pyridinium chlorochromate; sodium iodide; In tetrahydrofuran; dichloromethane; various solvents; acetone; 2.2: Suzuki-Miyaura coupling;
DOI:10.1016/j.tet.2005.06.115

Reference yield:

: 124177-10-2
(1R,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylenecyclohexaneethanol

: 866223-68-9
(R)-3-[2-(5,8-Dimethoxy-naphthalen-2-yl)-ethyl]-2,2-dimethyl-4-methylene-cyclohexanone

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridine / 4 °C

2.1: 923 mg / NaI / acetone / 4 h / Heating

3.1: t-BuLi; 9-methoxy-9-borabicyclo[3.3.1]nonane / various solvents / 1.42 h / -78 - 20 °C

3.2: 50 percent / K₃PO₄ / [Pd(PPh₃)4] / various solvents / 16 h / 80 °C

4.1: 90 percent / TBAF / tetrahydrofuran / 6 h / 50 - 60 °C

5.1: 63 percent / PCC / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; tetrabutyl ammonium fluoride; tert.-butyl lithium; 9-methoxy-9-BBN; pyridinium chlorochromate; sodium iodide; In tetrahydrofuran; dichloromethane; various solvents; acetone; 3.2: Suzuki-Miyaura coupling;
DOI:10.1016/j.tet.2005.06.115