3,3-二苯基丙醛

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4.69 mL (23.55 mmol, 1 eq.) of 3,3-diphenylpropanol are dissolved in 100 mL of CH2Cl2 under argon. 10.5 g (24.73 mmol, 1.05 eq.) of Dess Martin Periodinane (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one) are added to the mixture and the solution is stirred for 1 hour 30 min at 0° C. 100 mL of 2 M sodium hydroxide and 100 mL of CH2Cl2 are then added. The organic phase is washed with 2 M sodium hydroxide (twice), with water (twice), dried over MgSO4, filtered and concentrated. The crude reaction product is subjected to chromatography over silica gel (eluent: 5/1 heptane/AcOEt). An oil which crystallises in the form of a white product is recovered (4.76 g, yield=96%). The organic phase is washed with 2 M sodium hydroxide (twice), with water (twice), dried over MgSO4 filtered concentrated The crude reaction product An oil which crystallises in the form of a white product is recovered (4.76 g, yield=96%)

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4.69 mL (23.55 mmol, 1 eq.) of 3,3-diphenylpropanol are dissolved in 100 mL of CH2Cl2 under argon. 10.5 g (24.73 mmol, 1.05 eq.) of Dess Martin Periodinane (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one) are added to the mixture and the solution is stirred for 1 hour 30 min at 0° C. 100 mL of 2 M sodium hydroxide and 100 mL of CH2Cl2 are then added. The organic phase is washed with 2 M sodium hydroxide (twice), with water (twice), dried over MgSO4, filtered and concentrated. The crude reaction product is subjected to chromatography over silica gel (eluent: 5/1 heptane/AcOEt). An oil which crystallises in the form of a white product is recovered (4.76 g, yield=96%). The organic phase is washed with 2 M sodium hydroxide (twice), with water (twice), dried over MgSO4 filtered concentrated The crude reaction product An oil which crystallises in the form of a white product is recovered (4.76 g, yield=96%)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 3,3-diphenylpropionaldehyde (19.25 g, 91.54 mmoles) and 2-(3,4-dimethoxyphenyl)ethylamine (16.59 g, 1 equiv.) in 90% formic acid 125 mL) was heated at 95° C. for 16 hours. Upon cooling to room temperature, the solvent was removed on the rotary evaporator, and the residue was partitioned between ethyl acetate and 1M sodium hydroxide. The organic phase was washed with 1M sodium hydroxide and brine, dried over sodium sulfate, and evaporated to give a thick gum. The product was purified by flash chromatography on silica gel, eluting with 20:1 ethyl acetate/methanol, to give a thick gum that solidified upon standing (17.01 g, 50%). 1H-NMR (CDCl3) δ 2.42 (m, 1H), 2.53 (m, 1H), 2.67 (m, 2H), 2.98 (m, 1H), 3.18 (m, 1H), 3.77 (ABq, 1H), 3.84 and 3.88 (s, each 3H), 4.48 (ABq, 1H), 6.46 and 6.57 (s, each 1H), 7.32 (m, 10 H). Mass spec. 374.2 (MH)+. the solvent was removed on the rotary evaporator the residue was partitioned between ethyl acetate and 1M sodium hydroxide The organic phase was washed with 1M sodium hydroxide and brine dried over sodium sulfate evaporated to give a thick gum The product was purified by flash chromatography on silica gel eluting with 20:1 ethyl acetate/methanol to give a thick gum that

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4.69 mL (23.55 mmol, 1 eq) of 3,3-diphenyl-1-propanol are dissolved in 100 mL of CH2Cl2 under Ar. 10.5 g (24.73 mmol, 1.05 eq) of Dess Martin Periodinane are added and the solution is stirred for 1 hour 30 min at 0° C. 100 mL of 2 M sodium hydroxide and 100 mL of CH2Cl2 are added. The organic phase is washed with 2 M sodium hydroxide (twice), with water (twice), dried over MgSO4, filtered and concentrated. The crude reaction product is subjected to chromatography over silica gel (eluant: 5/1 heptane/AcOEt). An oil which crystallises in the form of a white product is recovered (4.76 g, yield=96%). The organic phase is washed with 2 M sodium hydroxide (twice), with water (twice), dried over MgSO4 filtered concentrated The crude reaction product An oil which crystallises in the form of a white product is recovered (4.76 g, yield=96%)

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4.69 mL (23.55 mmol, 1 eq.) of 3,3-diphenylpropanol are dissolved in 100 mL of CH2Cl2 under argon. 10.5 g (24.73 mmol, 1.05 eq.) of Dess Martin Periodinane (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one) are added to the mixture and the solution is stirred for 1 hour 30 min at 0° C. 100 mL of 2 M sodium hydroxide and 100 mL of CH2Cl2 are then added. The organic phase is washed with 2 M sodium hydroxide (twice), with water (twice), dried over MgSO4, filtered and concentrated. The crude reaction product is subjected to chromatography over silica gel (eluent: 5/1 heptane/AcOEt). An oil which crystallises in the form of a white product is recovered (4.76 g, yield=96%). The organic phase is washed with 2 M sodium hydroxide (twice), with water (twice), dried over MgSO4 filtered concentrated The crude reaction product An oil which crystallises in the form of a white product is recovered (4.76 g, yield=96%)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The 1,2-epoxy-4,4-diarylbutane starting materials can alternatively be prepared by reaction of dimethylsulfonium methylide or dimethyloxosulfonium methylide with an appropriate diarylalkyl aldehyde or a diarylalkyl ketone. For example, reaction of an aldehyde such as 3,3-diphenylpropanal with either dimethylsulfonium methylide or dimethyloxosulfonium methylide in approximately equimolar amounts provides 1,2-epoxy-4,4-diphenylbutane. Similarly, reaction of a diarylalkyl ketone such as methyl-(2,2-diphenylethyl) ketone with either dimethylsulfonium methylide or dimethyloxosulfonium methylide provides 1,2-epoxy-4,4-diphenyl-2-methylbutane. Such reactions typically are carried out in a solvent such as dimethyl sulfoxide or tetrahydrofuran, and normally at a reduced temperature of about 0° C. Dimethylsulfonium methylide is prepared by reaction of trimethylsulfonium iodide with methylsulfinylcarbanion, while demethyloxosulfonium methylide is prepared by reaction of trimethyloxosulfonium iodide with sodium hydride. Such reactions are more fully discussed by Corey et al., J. Am. Chem. Soc., 84, 867(1962) and J. Am. Chem. Soc., 84, 3782 (1962).

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The 1,2-epoxy-4,4-diarylbutane starting materials can alternatively be prepared by reaction of dimethylsulfonium methylide or dimethyloxosulfonium methylide with an appropriate diarylalkyl aldehyde or a diarylalkyl ketone. For example, reaction of an aldehyde such as 3,3-diphenylpropanal with either dimethylsulfonium methylide or dimethyloxosulfonium methylide in approximately equimolar amounts provides 1,2-epoxy-4,4-diphenylbutane. Similarly, reaction of a diarylalkyl ketone such as methyl-(2,2-diphenylethyl) ketone with either dimethylsulfonium methylide or dimethyloxosulfonium methylide provides 1,2-epoxy-4,4-diphenyl-2-methylbutane. Such reactions typically are carried out in a solvent such as dimethyl sulfoxide or tetrahydrofuran, and normally at a reduced temperature of about 0° C. Dimethylsulfonium methylide is prepared by reaction of trimethylsulfonium iodide with methylsulfinylcarbanion, while dimethyloxosulfonium methylide is prepared by reaction of trimethyloxosulfonium iodide with sodium hydride. Such reactions are more fully discussed by Corey et al., J. Am. Chem. Soc., 84, 867(1962) and J. Am. Chem. Soc., 84, 3782 (1962).

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 3,3-diphenylpropionaldehyde (19.25 g, 91.54 mmoles) and 2-(3,4-dimethoxyphenyl)ethylamine (16.59 g, 1 equiv.) in 90% formic acid 125 mL) was heated at 95° C. for 16 hours. Upon cooling to room temperature, the solvent was removed on the rotary evaporator, and the residue was partitioned between ethyl acetate and 1M sodium hydroxide. The organic phase was washed with 1M sodium hydroxide and brine, dried over sodium sulfate, and evaporated to give a thick gum. The product was purified by flash chromatography on silica gel, eluting with 20:1 ethyl acetate/methanol, to give a thick gum that solidified upon standing (17.01 g, 50%). 1H-NMR (CDCl3) δ 2.42 (m, 1H), 2.53 (m, 1H), 2.67 (m, 2H), 2.98 (m, 1H), 3.18 (m, 1H), 3.77 (ABq, 1H), 3.84 and 3.88 (s, each 3H), 4.48 (ABq, 1H), 6.46 and 6.57 (s, each 1H), 7.32 (m, 10 H). Mass spec. 374.2 (MH)+. the solvent was removed on the rotary evaporator the residue was partitioned between ethyl acetate and 1M sodium hydroxide The organic phase was washed with 1M sodium hydroxide and brine dried over sodium sulfate evaporated to give a thick gum The product was purified by flash chromatography on silica gel eluting with 20:1 ethyl acetate/methanol to give a thick gum that

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4.69 mL (23.55 mmol, 1 eq) of 3,3-diphenyl-1-propanol are dissolved in 100 mL of CH2Cl2 under Ar. 10.5 g (24.73 mmol, 1.05 eq) of Dess Martin Periodinane are added and the solution is stirred for 1 hour 30 min at 0° C. 100 mL of 2 M sodium hydroxide and 100 mL of CH2Cl2 are added. The organic phase is washed with 2 M sodium hydroxide (twice), with water (twice), dried over MgSO4, filtered and concentrated. The crude reaction product is subjected to chromatography over silica gel (eluant: 5/1 heptane/AcOEt). An oil which crystallises in the form of a white product is recovered (4.76 g, yield=96%). The organic phase is washed with 2 M sodium hydroxide (twice), with water (twice), dried over MgSO4 filtered concentrated The crude reaction product An oil which crystallises in the form of a white product is recovered (4.76 g, yield=96%)

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4.69 mL (23.55 mmol, 1 eq.) of 3,3-diphenylpropanol are dissolved in 100 mL of CH2Cl2 under argon. 10.5 g (24.73 mmol, 1.05 eq.) of Dess Martin Periodinane (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one) are added to the mixture and the solution is stirred for 1 hour 30 min at 0° C. 100 mL of 2 M sodium hydroxide and 100 mL of CH2Cl2 are then added. The organic phase is washed with 2 M sodium hydroxide (twice), with water (twice), dried over MgSO4, filtered and concentrated. The crude reaction product is subjected to chromatography over silica gel (eluent: 5/1 heptane/AcOEt). An oil which crystallises in the form of a white product is recovered (4.76 g, yield=96%). The organic phase is washed with 2 M sodium hydroxide (twice), with water (twice), dried over MgSO4 filtered concentrated The crude reaction product An oil which crystallises in the form of a white product is recovered (4.76 g, yield=96%)