adamantane

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 10 mmol of ethyl acrylate, 50 mmol of adamantane, 1 mmol of N-hydroxyphthalimide, 0.01 mmol of cobalt(II) acetate, 0.1 mmol of acetylacetonatocobalt(III), and 54 mmol of acetonitrile was stirred at 70° C. in an oxygen atmosphere (1 atm) for 8 hours. A reaction mixture was concentrated, and the concentrate was subjected to column chromatography on a silica gel to yield ethyl 3-(adamant-1-yl)-2-hydroxypropionate of the following formula (a), ethyl 3-(adamant-1-yl)-2-oxopropionate of the following formula (b), and ethyl 1-adamantaneacetate of the following formula (c) in yields of 55%, 16%, and 8%, respectively. The conversion rate from ethyl acrylate was 99%. A reaction mixture was concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Aluminum trichloride (40 g, 3 mol) was added slowly to thionyl chloride (200 ml, 2.7 mol), and the mixture was cooled to -20°. Adamantane was added in portions over 21/2 hrs, and the resulting mixture was stirred 1 hr and allowed to warm to room temperature. After the thionyl chloride was removed under vacuum, the residue was diluted with CCl4 ; and the aluminum trichloride was decomposed with ice and water. The layers were separated; and the organic layer was washed (brine), dried (Na2SO4), filtered, and concentrated under vacuum. The residue was distilled under vacuum (1 torr, 133.3 Pascals) with a vigreaux column to give the product (28.8 g; bp 118°-128°) as a waxy solid; TLC, Rf =0.6-0.4, EtOAc:hexanes (15:85). the mixture was cooled to -20° After the thionyl chloride was removed under vacuum the residue was diluted with CCl4 The layers were separated and the organic layer was washed (brine) dried (Na2SO4) filtered concentrated under vacuum The residue was distilled under vacuum (1 torr, 133.3 Pascals) with a vigreaux column to give the product (28.8 g; bp 118°-128°) as a waxy solid

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Reaction of catechol with 1,3-adamantane-diol according to the method described by Lu et al (Lu et al. J Med Chem 2005, 48 (14), 4576-4585) gave the adduct 10 in reasonable yield.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Reaction of catechol with 1,3-adamantane-diol according to the method described by Lu et al (Lu et al. J Med Chem 2005, 48 (14), 4576-4585) gave the adduct 10 in reasonable yield.