Benzoic acid (1R,2S,5S,7S)-7-methyl-7-vinyl-bicyclo[3.3.1]non-2-yl ester

Base Information

Chemical Name:Benzoic acid (1R,2S,5S,7S)-7-methyl-7-vinyl-bicyclo[3.3.1]non-2-yl ester
CAS No.:132514-50-2
Molecular Formula:C₁₉H₂₄O₂
Molecular Weight:284.398
Hs Code.:

Synonyms:Benzoic acid (1R,2S,5S,7S)-7-methyl-7-vinyl-bicyclo[3.3.1]non-2-yl ester

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Chemical Property of Benzoic acid (1R,2S,5S,7S)-7-methyl-7-vinyl-bicyclo[3.3.1]non-2-yl ester

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Technology Process of Benzoic acid (1R,2S,5S,7S)-7-methyl-7-vinyl-bicyclo[3.3.1]non-2-yl ester

There total 19 articles about Benzoic acid (1R,2S,5S,7S)-7-methyl-7-vinyl-bicyclo[3.3.1]non-2-yl ester 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: 92.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 123099-74-1
Benzoic acid (1R,2S,5S,7S)-7-formyl-7-methyl-bicyclo[3.3.1]non-2-yl ester

: 132514-50-2
Benzoic acid (1R,2S,5S,7S)-7-methyl-7-vinyl-bicyclo[3.3.1]non-2-yl ester

Guidance literature:: With n-butyllithium; at -78 - 25 ℃; for 20h;
DOI:10.1021/ja00202a064

Reference yield:

: 876-53-9
1,3-dibromoadamantane

: 132514-50-2
(R,S)-(1l,2u,5u,7u)-2-(benzoyloxy)-7-methyl-7-ethenylbicyclo<3.3.1>nonane

Guidance literature:: Multi-step reaction with 12 steps

1: 83 percent / 1 M NaOH / dioxane / 16 h / 185 °C

2: 1.) BF₃*THF, 2.) 10percent NaOH, 30percent aq. H₂O₂ / 1.) RT, 90 min, 2.) a) RT, 20 min, b) 50 deg C, 15 min

3: 80 percent / imidazole, DMAP / dimethylformamide / 1.) RT, 5 h, 2.) 45 deg C, overnight

4: 100 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

5: 92 percent / t-BuOK / tetrahydrofuran / 2 h / Ambient temperature

6: 98 percent / m-chloroperoxybenzoic acid, NaHCO₃ / CH₂Cl₂ / 1 h / Ambient temperature

7: 72 percent / lithium triethylborohydride / tetrahydrofuran / 4 h / 45 °C

8: 1.) n-BuLi / 1.) Et₂O, -5 deg C, 5 min, 2.) RT, 30 min

9: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 8 h / Ambient temperature

10: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) Et₃N / 1.) -78 deg C, 30 min, 2.) from -78 deg C to RT, 35 min

11: 1.) t-BuOK / 1.) THF, 2-methyl-2-propanol, RT, 5 min, 2.) RT, 35 min

12: 1.) n-BuLi / 1.) THF, hexane, RT, 2.) RT, 20 min

With 1H-imidazole; dmap; sodium hydroxide; n-butyllithium; oxalyl dichloride; boron trifluoride-tetrahydrofuran complex; potassium tert-butylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; lithium triethylborohydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00006a042

Reference yield:

: 768-90-1
1-Adamantyl bromide

: 132514-50-2
(R,S)-(1l,2u,5u,7u)-2-(benzoyloxy)-7-methyl-7-ethenylbicyclo<3.3.1>nonane

Guidance literature:: Multi-step reaction with 13 steps

1: 87 percent / Br₂, AlBr₃, BBr₃ / 1.5 h / 85 °C

2: 83 percent / 1 M NaOH / dioxane / 16 h / 185 °C

3: 1.) BF₃*THF, 2.) 10percent NaOH, 30percent aq. H₂O₂ / 1.) RT, 90 min, 2.) a) RT, 20 min, b) 50 deg C, 15 min

4: 80 percent / imidazole, DMAP / dimethylformamide / 1.) RT, 5 h, 2.) 45 deg C, overnight

5: 100 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

6: 92 percent / t-BuOK / tetrahydrofuran / 2 h / Ambient temperature

7: 98 percent / m-chloroperoxybenzoic acid, NaHCO₃ / CH₂Cl₂ / 1 h / Ambient temperature

8: 72 percent / lithium triethylborohydride / tetrahydrofuran / 4 h / 45 °C

9: 1.) n-BuLi / 1.) Et₂O, -5 deg C, 5 min, 2.) RT, 30 min

10: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 8 h / Ambient temperature

11: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) Et₃N / 1.) -78 deg C, 30 min, 2.) from -78 deg C to RT, 35 min

12: 1.) t-BuOK / 1.) THF, 2-methyl-2-propanol, RT, 5 min, 2.) RT, 35 min

13: 1.) n-BuLi / 1.) THF, hexane, RT, 2.) RT, 20 min

With 1H-imidazole; dmap; sodium hydroxide; n-butyllithium; aluminum tri-bromide; oxalyl dichloride; boron trifluoride-tetrahydrofuran complex; potassium tert-butylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; bromine; boron tribromide; lithium triethylborohydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00006a042