* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Bulletin of the Chemical Society of Japan, 1988, vol. 61, # 7, p. 2393 - 2399
[2] Bulletin of the Chemical Society of Japan, 1988, vol. 61, # 7, p. 2393 - 2399
2
[ 1829-60-3 ]
[ 34911-25-6 ]
Reference：
[1] Bulletin of the Chemical Society of Japan, 1988, vol. 61, # 7, p. 2393 - 2399
[2] Bulletin of the Chemical Society of Japan, 1988, vol. 61, # 7, p. 2393 - 2399
[3] Chemistry Letters, 1987, p. 1557 - 1560
(1R,4S,4aS,8aR)-dimethyl 6,7-dimethyl-1,4,4a,5,8,8a-hexahydro-1,4-epoxynaphthalene-4a,8a-dicarboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
98%
With acetic acid In chloroform at 25℃; for 24h; diastereoselective reaction;
Diels-Alder reaction of dimethyl 7-oxo-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate (3) with 2,3-dimethyl-1,3-butadiene
Diene 3 (0.5 g, 2.4 mmol) and 2,3-dimethyl-1,3-butadiene 4(0.197 g, 2.4 mmol) was dissolved in 10 mL of chloroform, and thenthe reaction was stirred at room temperature for 48 days. After thereaction, the solvent was removed to give product
(1R,4S,4aS,8aR)-dimethyl 6,7-dimethyl-1,4,4a,5,8,8a-hexahydro-1,4-epoxynaphthalene-4a,8a-dicarboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
1: 90%
2: 10%
With acetic acid In chloroform at 25℃; for 30h; diastereoselective reaction;
Diels-Alder reaction of dimethyl 7-oxo-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate (3) with 2,3-dimethyl-1,3-butadiene
(Diene 3 (0.5 g, 2.4 mmol) and 2,3-dimethyl-1,3-butadiene 4(0.197 g, 2.4 mmol) was dissolved in 10 mL of chloroform, and thenthe reaction was stirred at room temperature for 48 days. After thereaction, the solvent was removed to give product
(1R,4S,4aS,8aR)-dimethyl 6,7-dimethyl-1,4,4a,5,8,8a-hexahydro-1,4-epoxynaphthalene-4a,8a-dicarboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
20%; 60%; 20%
With acetic acid; In chloroform; at 25℃; for 360h;
Diene 3 (0.5 g, 2.4 mmol) and 2,3-dimethyl-1,3-butadiene 4(0.197 g, 2.4 mmol) was dissolved in 10 mL of chloroform, and thenthe reaction was stirred at room temperature for 48 days. After thereaction, the solvent was removed to give product
With acetic acid; In chloroform; at 25℃; for 1152h;
(Diene 3 (0.5 g, 2.4 mmol) and 2,3-dimethyl-1,3-butadiene 4(0.197 g, 2.4 mmol) was dissolved in 10 mL of chloroform, and thenthe reaction was stirred at room temperature for 48 days. After thereaction, the solvent was removed to give product
33%; 67%
With acetic acid; In chloroform; at 25℃; for 720h;
(Diene 3 (0.5 g, 2.4 mmol) and 2,3-dimethyl-1,3-butadiene 4(0.197 g, 2.4 mmol) was dissolved in 10 mL of chloroform, and thenthe reaction was stirred at room temperature for 48 days. After thereaction, the solvent was removed to give product
(cis)-3-methyl-4-carboxylic acid methyl ester 2-(2-(trimethylsilyl)vinyl)phenyltrimethylsilane[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
60%
With palladium diacetate; potassium carbonate; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃; for 12h;Inert atmosphere;
0.2 mmol of potassium carbonate and 0.01 mmol of palladium acetate.0.02 mmol of triphenylphosphine, 0.2 mmol of methyl 2,3-dicarboxylate-7-oxanorbornadiene,2-fluoro-3-carboxylic acid methyl ester iodobenzene 0.1 mmol, hexamethyldisiloxane 0.15 mmol,1 mL of N,N-dimethylformamide was added to a 15 mL reaction tube.Nitrogen was repeatedly filled 3 times, placed in an oil bath at 100 C, and reacted for 12 h;After cooling to room temperature, the reaction solution was diluted with ethyl acetate and washed with water three times.The organic phase was dried over anhydrous Na2SO4, filtered and concentrated.Purified by column chromatography19.2mg of target product,The yield was 60%.
(Z)-(3,5-dimethoxy-2-(2-(trimethylsilyl) vinyl)phenyl)trimethylsilane[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
82%
With trifuran-2-yl-phosphane; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 12h; Schlenk technique; Inert atmosphere;
(cis)-3-methyl-5-carboxylic acid methyl ester-2-(2-(trimethylsilyl)vinyl)phenyltrimethylsilane[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
70%
With palladium diacetate; potassium carbonate; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃; for 12h;Inert atmosphere;
0.2 mmol of potassium carbonate and 0.01 mmol of palladium acetate.Triphenylphosphine 0.02mmol,Methyl 2,3-dicarboxylate-7-oxanorbornadiene 0.2 mmol,2-fluoro-4-carboxylic acid methyl ester iodobenzene 0.1 mmol,Hexamethyldisiloxane 0.15mmol,1 mL of N,N-dimethylformamide was added to a 15 mL reaction tube.Nitrogen was repeatedly filled 3 times, placed in an oil bath at 100 C, and reacted for 12 h;After cooling to room temperature, the reaction solution was diluted with ethyl acetate and washed with water three times.The organic phase was dried over anhydrous Na2SO4, filtered and concentrated.Purified by column chromatography22.4 mg of target product,The yield was 70%.
(cis)-(3-acetamido-2-(2-(trimethylsilyl)vinyl)phenyl)trimethylsilane[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
62%
With palladium diacetate; potassium carbonate; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃; for 12h;Inert atmosphere;
Potassium carbonate 0.2mmol, palladium acetate 0.01mmol, triphenylphosphine 0.02mmol, 2,3-dicarboxylate methyl ester-7-oxanorbornadiene 0.2mmol, 2-acetamidoiodobenzene 0.1mmol, Rouge 0.15mmol of disilicone and 1mL of N,N-dimethylformamide were added to a 15mL reaction tube, and the nitrogen was repeatedly filled 3 times, placed in an oil bath at 100 C for 12 hours; cooled to room temperature, and the reaction solution was treated with acetic acid. The ethyl ester was diluted, washed three times with water, and the organic phase was dried over anhydrous Na2SO4.Filtration, concentration and purification by column chromatography gave 18.9 mg of the desired product.The yield was 62%.
(cis)-2-methoxy-4-(trimethylsilyl)-3-(2-(trimethylsilyl)vinyl)pyridine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
17.9%
With palladium diacetate; potassium carbonate; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃; for 12h;Inert atmosphere;
0.2 mmol of potassium carbonate and 0.01 mmol of palladium acetate.0.02 mmol of triphenylphosphine, 0.2 mmol of methyl 2,3-dicarboxylate-7-oxanorbornadiene, 0.1 mmol of 2-iodo-3methoxypyridine, 0.15 mmol of hexamethyldisiloxane, N, 1 mL of N-dimethylformamide was added to a 15 mL reaction tube, nitrogen was repeatedly filled 3 times, placed in an oil bath at 100 C, and reacted for 12 h;After cooling to room temperature, the reaction solution was diluted with ethyl acetate and washed with water three times.The organic phase was dried over anhydrous Na2SO4, filtered and concentrated.Purified by column chromatography17.9mg of target product,The yield was 64%.
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