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CAS No. : | 141779-46-6 | MDL No. : | N/A |
Formula : | C22H14O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DENRDANQMQOFEU-UHFFFAOYSA-N |
M.W : | 342.34 | Pubchem ID : | 11056994 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With hydrogenchloride In tetrahydrofuran at 20℃; for 3h; | |
99% | With hydrogenchloride In tetrahydrofuran for 1.5h; Inert atmosphere; | 1 Next, formylbinaphthol (133 mg, 0.31 mmol) in which the phenolic hydroxyl group was protected with MOM was dissolved in anhydrous THF (2.6 ml), hydrochloric acid (12 M, 1.1 ml) was added while ice- , Stir under an argon atmosphere for 1 hour and 30 minutes, extract in the order of ethyl acetate, distilled water, saturated sodium bicarbonate aqueous solution and saturated brine.The organic layer was dried with sodium sulfate and concentrated under reduced pressure to give formyl binaphthol in the form of a yellow powder represented by the above formula (4-2) in a yield of 99%. |
96% | With hydrogenchloride; water In tetrahydrofuran at 0 - 20℃; for 3.08333h; |
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 3h; | ||
With hydrogenchloride In tetrahydrofuran at 0 - 20℃; for 3h; | ||
With hydrogenchloride In tetrahydrofuran; water Schlenk technique; | ||
With hydrogenchloride In water | Next, formin binaphthol represented by the following formula (D) can be obtained by removing the MOM group in the presence of hydrochloric acid with respect to the binaphthol represented by (C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With formic acid In methanol for 4h; Reflux; | 3.2. Synthesis of LH2 (R) To a stirred solution of (R)-2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarbaldehyde (1.0 g, 2.9 mM) in methanol (20 mL) were added 2-methoxyaniline (0.76 g, 6.1 mM) and formic acid (1 drop) as a catalyst. The mixture was refluxed for 4 h to yield an orange precipitate. The crude product was filtered at room temperature and washed with ice-cold ethanol to afford pure ligand as an orange solid in 85% yield (1.37 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With potassium carbonate In ethanol; water at 20℃; for 24h; | Synthesis of ligand 1 A mixture of 0.26 g (0.979 mmol) of (1R,2R)-cyclohexane diamine mono-l-tartrate and 0.27 g (1.958 mmol) of potassium carbonate was dissolved in 3 ml of 50% aqueous ethanol solution. The resulting mixture was added to a suspension of 0.335 g (0.979 mmol) of (R)-3,3′-diformyl-BINOL in 7 ml of ethanol. The reaction mixture was stirred at room temperature for 24 h. The resulting precipitate was filtered of and washed with ethanol and dried under vacuum. Yield of light-yellow solid was 0.5g (61%). 1H NMR (400MHz, CDCl3) δ 13.21 (br s, 4H), 8.47 (s, 4H), 7.75 (m, 8H), 7.28 (m, 4H), 6.96 (m, 8H), 3.31 (m, 4H), 1.82-1.92 (m, 8H), 1.40-1.61 (m, 8H). [α]D25=-214 (c 0.25, CH2Cl2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sodium hydroxide In methanol at 20℃; for 12h; | Synthesis and characterization of 2 To (R)-1 (100 mg, 0.29 mmol) and L-Trp (120 mg, 0.58 mmol) dissolved in MeOH (5 mL) in a round bottom flask (25 mL) were added with NaOH (23.2 mg, 0.58 mmol) and the resulting mixture was stirred at room temperature for 12 h. After removal of the solvent under vacuum, the product 2 was obtained in 97% yield (215 mg, 0.28 mmol). 1H NMR (400 MHz, CD3OD), δ 8.15 (s, 2H), 7.79 (d, J = 8.0 Hz, 2H), 7.76 (s, 2H), 7.60 (d, J = 8.0 Hz, 2H), 7.27-7.21 (m, 6H), 7.01-6.97 (m, 6 H), 6.88 (t, J = 7.2 Hz, 2H), 4.14 (dd, J1 = 9.6 Hz, J2 = 4.0 Hz, 2H), 3.49 (dd, J1 = 14.4 Hz, J2 = 4.0 Hz, 2H), 3.18 (dd, J1 = 14.4 Hz, J2 = 9.6 Hz, 2H). 13C NMR (100 MHz, CD3OD) δ 178.12 (s, 2H), 164.76 (s, 3H), 154.38 (s, 2H), 136.54 (s, 2H), 135.13 (s, 2H), 128.40 (s, 3H), 127.52 (d, J = 19.4 Hz, 6H), 123.13 (s, 3H), 122.61 (s, 3H), 121.22 (s, 2H), 120.62 (s, 3H), 118.21 (d, J = 10.4 Hz, 7H), 116.24 (s, 1H), 111.41 (s, 2H), 110.61 (s, 3H), 76.86 (s, 4H), 48.20 (s, 9H), 47.99 (s, 28H), 47.78 (s, 56H), 47.56 (s, 64H), 47.35 (s, 57H), 47.14 (s, 28H), 46.92 (s, 10H), 30.33 (s, 2H). HRMS Calcd for C44H35N4O6 (M+H+): 715.2551. Found: 715.2538. HRMS Calcd for C44H34N4O6Na (M+Na+): 737.2371. Found: 737.2347. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With toluene-4-sulfonic acid In ethanol at 80℃; | 2.2.2 Synthesis of (R)-/(S)-4b (R)-/(S)-3 (574 mg, 1.7 mmol) and N,N-dimethyl-1,4-phenylenediamine (0.46 mL, 3.7 mmol) were added into 35 mL of EtOH, and then p-toluenesulfonic acid (20 mg, 0.12 mmol) was added to the solution. The mixture was stirred for 4 h at 80 °C. After completion of the reaction, the solvents were cooled to room temperature; (R)-/(S)-4b were obtained by filtration as a grass green solid. (R)-4b: (776 mg, 80%). m.p. 371-372 °C. (S)-4b: (717 mg, 74%). m.p. 396-397 °C. 1H NMR (300 MHz, CDCl3) δ (ppm), 13.66 (s, 2H), 8.88 (s, 2H), 8.04 (s, 2H), 7.88 (dd, J=3.0, 3.0 Hz, 2H), 7.26 (d, J=9.0 Hz, 10H), 6.70 (d, J=9.0 Hz, 4H), 2.96 (s, 12H). 13C NMR (75 MHz, CDCl3) δ (ppm), 157.3, 155.0, 150.2, 137.0, 135.5, 133.5, 129.0, 128.3, 128.0, 125.0, 123.5, 122.5, 122.2, 117.0, 112.9, 40.7. HRMS (ESI+): calcd for C38H35N4O2+: [M+H]+ =579.2760, found: [M+H]+= 579.2756. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | (2) The compound of the formula IIa (2 g, 5.3 mmol) and 50 ml of anhydrous THF were placed in a reactor equipped with a stirring apparatus, and n-BuLi (1.4 ml, 2.26 mmol) was added at 0 C under stirring. , 2.5M in hexane), added, kept in this state for at least 15 minutes; warmed to room temperature and stirred at room temperature for at least 3 hours; again cooled the reaction system to 0 C state, and into the reaction system DMF (7.5 ml, 18.7 mmol) was added and kept at 0 C for at least 30 minutes; the temperature was raised again to room temperature and stirring was continued, and the reaction was stopped by TLC until the starting point (the compound of formula IIa) disappeared, and a saturated aqueous solution of ammonium chloride was added. After the reaction was quenched, 2 ml of 1N-hydrochloric acid was added, and the mixture was extracted with ethyl acetate (3 times). The organic phase was combined and washed with saturated sodium hydrogen carbonate and brine. The solvent was removed under reduced pressure and purified by silica gel column chromatography (ethyl ether: ethyl acetate = 15:1).The yield was 78%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With potassium carbonate In propan-2-one at 60℃; for 6h; | 1.4 (4) Synthesis of compound (R)-4 K2CO3(2.20g, 16.0 mmol), (R)-3 (0.68 g, 2.0 mmol), 2-bromo-4'-(trifluoromethyl)acetophenone (0.91 g, 4.8 mmol) and 30 ml acetone were added to a 100 ml monoglycerical flask. After 60 °C heating and stirring for 6h, it is cooled to room temperature. Distillation to remove solvents under reduced pressure, add 50 mL of water, extract with ethyl acetate (3×50 mL), combine the organic phase, add saturated brine (3×50 mL) to wash the organic phase, anhydrousNa2SO4dry, reduce pressure distillation to remove the solvent. The yellow powder was separated by 300~400 mesh silica gel and PE:DCM=1:1 eluent column chromatography, and then recrystallized by EA to obtain a yellow needle-like solid of 0.8g ((R)-4), with a yield of 59%. |
A440940[ 121314-69-0 ]
(R)-2,2'-Dihydroxy-[1,1'-binaphthalene]-3,3'-dicarboxaldehyde
Reason: Optical isomers