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CAS No. : | 216369-04-9 | MDL No. : | |
Formula : | C32H24NP | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 453.51 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
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Multi-step reaction with 2 steps 1: 81 percent / NaBH4, aq. H2SO4 / tetrahydrofuran / 0.25 h / Ambient temperature 2: 85 percent / NaBH4, aq. H2SO4 / tetrahydrofuran / 0.25 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
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700 mg (72%) | With trichlorosilane; sodium hydrogencarbonate; triethylamine In dichloromethane; para-xylene | S-(+)-2-Amino-2'-(diphenylphosphino)-1,1'-binaphthyl (11): S-(+)-2-Amino-2'-(diphenylphosphino)-1,1'-binaphthyl (11): 3.0 mL of trichlorosilane (4.0 g, 29.8 mmol) was added to a mixture of 1.01 g of 10 (2.15 mmol) and 5.0 mL of triethylamine (3.63 g, 3.59 mmol) in 80 mL of p-xylene at ice-bath. The mixture was stirred at 0° C. for 0.5 h and then heated to 120° C. for 5 h. After cooling to room temperature, 100 mL of dichloromethane and 10 mL of saturated NaHCO3 solution were added to the reaction mixture. The resulting suspension was stirred for 0.5 h and filtered through a Celite. The solid residue was extracted with dichloromethane and washed with water. The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The resulting solution was loaded on a silica gel column (50 g) and eluted with CH2Cl2 to afford 700 mg (72%) of 11 as a white solid. [α]D25+28.1 (c 1.0, THF), 1H NMR (CDCl3) δ 3,22 (bs, 2H), 6.75 (d, J=8.4 Hz, 1H), 7.00-7.07 (m, 2H), 7.13-7.25 (m, 6H), 7.34-7.41 (m, 7H), 7.52-7.56 (m, 2H), 7.79 (d, J=8.1 Hz, 1H), 7.85 (d, J=8.7 Hz, 1H), 7.95 (d, J=8.3 Hz, 2H), 31P NMR δ -13.43 (s), FAB-MS m/z 453.1 M+. |
With trichlorosilane; ammonium chloride; triethylamine In 5,5-dimethyl-1,3-cyclohexadiene; hexane; ethyl acetate | R.1 Synthesis of (-)-2-amino-2'-diphenylphosphino-1,1'-binaphthyl: the formula (1-1a) Reference Example 1 Synthesis of (-)-2-amino-2'-diphenylphosphino-1,1'-binaphthyl: the formula (1-1a) 7.16 gram (15.2 mmol) of (-)-2-amino-2'-diphenylphosphinyl-1,1'-binaphthyl (the formula (1-1a-1) was dissolved in 381 ml of xylene in an autoclave, followed by the addition of 42.5 ml (305.0 mmol) of triethylamine at 0° C. over 20 minutes and 7.70 ml (76.3 mmol) of trichlorosilane over 1 hour. The mixture was stirred at 150° C. for 18 hours in a tightly sealed condition. The reaction mixture was then extracted with 500 ml of ether. The extract was washed with 200 ml of saturated aqueous solution of ammonium chloride and 200 ml of brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure. The residue was purified using a silica gel column chromatography (eluent: 1:4 mixture of ethyl acetate and hexane) to obtain 5.60 gram of the titled compound. mp: 104.7° C. 1H-NMR (CDCl3) δ: 7.87 (d, J=8.3 Hz, 2H), 7.77 (d, J=8.7 Hz, 1H), 7.71 (d, J=7.8 Hz, 1H), 7.5-7.4 (m, 2H), 7.4-7.2(m, 7H), 7.2-7.0(m, 6H), 7.0-6.9(m, 2H), 6.67(d, J=8.8 Hz, 1H), 3.25(bs, 2H) 31P-NMR (CDCl3): δ: -13.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,2-dichloro-ethane | 14 Synthesis of citronellol by the asymmetric hydrogenation of geraniol Example 14 Synthesis of citronellol by the asymmetric hydrogenation of geraniol 4.5 mg (0.01 mmol) of (-)-2-amino-2'-diphenylphosphino-1,1'-binaphthyl (the formula (1-1a)), 5.0 mg (0.01 mmol) of bis(1,5-cyclooctadiene)iridium tetrafluoroborate, 154 mg (1.0 mmol) of geraniol and 2 ml of ethylene chloride were charged into an autoclave and stirred at 30° C. for 20 hours in hydrogen atmosphere under a pressure of 4 atm. The solvent of the resultant reaction solution was evaporated under a reduced pressure. The residue was then measured by means of a gas chromotography to confirm the formation of citronelol with a chemical yield of 77 percent. The optical yield of citronellol was 96 percent confirmed by an optically active HPLC column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; ammonium chloride In hexane; dichloromethane; ethyl acetate | 7 Synthesis of (+)-2-acetylamino-2'-diphenylphosphino-1,1'-binaphthyl: the formula (1-2a) Example 7 Synthesis of (+)-2-acetylamino-2'-diphenylphosphino-1,1'-binaphthyl: the formula (1-2a) 1.15 gram (2.54 mmol) of (-)-2-amino-2'-diphenylphosphino-1,1'-binaphthyl (the formula (1-1a)) was dissolved in 51 ml of methylene chloride, followed by the addition of 0.25 ml (3.04 mmol) of pyridine and 0.20 ml (2.78 mmol) of acetyl chloride under 0° C. The reaction mixture was stirred at room temperature for 3 hours. To the reaction solution, 30 ml of saturated aqueous solution of ammonium chloride was added and extracted with 100 ml of methylene chloride. The extract was washed with 70 ml of brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure. The residue was purified using a silica gel column chromatography (eluent: 1:3 mixture of ethyl acetate and hexane) to obtain 1.11 gram of the titled compound. mp: 104.8° C. 1H-NMR (CDCl3) δ: 8.47(d, J=9.1 Hz, 1H), 8.1-7.8(m, 4H), 7.6-7.4(m, 2H), 7.4-7.0(m, 14H), 6.89(d, J=8.4 Hz, 1H), 6.26(bs, 1H), 1.43(bs, 3H) 31P-NMR (CDCl3): δ: -13.7 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; ammonium chloride In hexane; dichloromethane; ethyl acetate | 8 Synthesis of (-)-2-benzoylamino-2'-diphenylphosphino-1,1'-binaphthyl: the formula (1-2c) Example 8 Synthesis of (-)-2-benzoylamino-2'-diphenylphosphino-1,1'-binaphthyl: the formula (1-2c) 1.00 gram (2.21 mmol) of (-)-2-amino-2'-diphenylphosphino-1,1'-binaphthyl (the formula (1-1a)) was dissolved in 44 ml of methylene chloride, followed by the addition of 0.21 ml (2.65 mmol) of pyridine and 0.28 ml (2.43 mmol) of benzoyl chloride under 0° C. The reaction mixture was stirred at room temperature for 5 hours. To the reaction solution, 30 ml of saturated aqueous solution of ammonium chloride was added and extracted with 100 ml of methylene chloride. The extract was washed with 70 ml of brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure. The residue was purified using a silica gel column chromatography (eluent: 1:6 mixture of ethyl acetate and hexane) to obtain 1.16 gram of the titled compound. mp: 94.8° C. 1H-NMR (CDCl3) δ: 8.68(d, J=9.0 Hz, 1H), 8.06(d, J=9.0 Hz, 1H), 7.92(d, J=8.5 Hz, 1H), 7.9-7.8(m, 2H), 7.6-7.4(m, 2H), 7.4-6.9(m, 21H) 31P-NMR (CDCl3): δ: -13.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; ammonium chloride In hexane; dichloromethane; ethyl acetate | 6 Synthesis of (+)-2-methoxycarbonylamino-2'-diphenylphosphino-1,1'-binaphthyl: the formula (1-2b) Example 6 Synthesis of (+)-2-methoxycarbonylamino-2'-diphenylphosphino-1,1'-binaphthyl: the formula (1-2b) 1.20 gram (2.65 mmol) of (-)-2-amino-2'-diphenylphosphino-1,1'-binaphthyl (1-1a) was dissolved in 53 ml of methylene chloride, followed by the addition of 0.26 ml (3.18 mmol) of pyridine and 0.23 ml (2.91 mmol) of methyl chloroformate under 0° C. The reaction mixture was stirred at room temperature for 21 hours. To the reaction solution, 40 ml of saturated aqueous solution of ammonium chloride was added and extracted with 100 ml of methylene chloride. The extract was washed with 80 ml of brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure. The residue was purified using a silica gel column chromatography (eluent: 1:4 mixture of ethyl acetate and hexane) to obtain 1.25 gram of the titled compound. mp: 92.1° C. 1H-NMR (CDCl3) δ: 8.39(bs, 1H), 8.0-7.8(m, 4H), 7.6-7.4(m, 2H), 7.4-6.9(m, 14H), 6.81(d, J=8.6 Hz, 1H), 5.94(bs, 1H), 3.45(s, 3H) 31P-NMR (CDCl3): δ: -13.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In tetrahydrofuran at 60℃; for 153h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In tetrahydrofuran at 60℃; for 153h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In tetrahydrofuran at 60℃; for 153h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol Reflux; | General procedure of the preparation of chiral phosphine-Schiff base type ligands L1-L13 General procedure: To a solution of (R)-(-)-2-(diphenylphosphino)-1,1'-binaphthyl-2'-amine1,2 (227 mg, 0.5 mmol) in absolute ethanol (4.0 mL) was added salicylaldehydes (0.5 mmol) or its analogues (0.5 mmol) at room temperature and the reaction mixture was stirred under reflux overnight. After cooling to room temperature, precipitates settled out, which were filtered to give the corresponding phosphine-salen type ligands and phosphine-Schiff base type ligands L1-L13 in good yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | In ethanol Reflux; | General procedure of the preparation of chiral phosphine-Schiff base type ligands L1-L13 General procedure: To a solution of (R)-(-)-2-(diphenylphosphino)-1,1'-binaphthyl-2'-amine1,2 (227 mg, 0.5 mmol) in absolute ethanol (4.0 mL) was added salicylaldehydes (0.5 mmol) or its analogues (0.5 mmol) at room temperature and the reaction mixture was stirred under reflux overnight. After cooling to room temperature, precipitates settled out, which were filtered to give the corresponding phosphine-salen type ligands and phosphine-Schiff base type ligands L1-L13 in good yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol Reflux; | General procedure of the preparation of chiral phosphine-Schiff base type ligands L1-L13 General procedure: To a solution of (R)-(-)-2-(diphenylphosphino)-1,1'-binaphthyl-2'-amine1,2 (227 mg, 0.5 mmol) in absolute ethanol (4.0 mL) was added salicylaldehydes (0.5 mmol) or its analogues (0.5 mmol) at room temperature and the reaction mixture was stirred under reflux overnight. After cooling to room temperature, precipitates settled out, which were filtered to give the corresponding phosphine-salen type ligands and phosphine-Schiff base type ligands L1-L13 in good yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol Reflux; | General procedure of the preparation of chiral phosphine-Schiff base type ligands L1-L13 General procedure: To a solution of (R)-(-)-2-(diphenylphosphino)-1,1'-binaphthyl-2'-amine1,2 (227 mg, 0.5 mmol) in absolute ethanol (4.0 mL) was added salicylaldehydes (0.5 mmol) or its analogues (0.5 mmol) at room temperature and the reaction mixture was stirred under reflux overnight. After cooling to room temperature, precipitates settled out, which were filtered to give the corresponding phosphine-salen type ligands and phosphine-Schiff base type ligands L1-L13 in good yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | In ethanol Reflux; | General procedure of the preparation of chiral phosphine-Schiff base type ligands L1-L13 General procedure: To a solution of (R)-(-)-2-(diphenylphosphino)-1,1'-binaphthyl-2'-amine1,2 (227 mg, 0.5 mmol) in absolute ethanol (4.0 mL) was added salicylaldehydes (0.5 mmol) or its analogues (0.5 mmol) at room temperature and the reaction mixture was stirred under reflux overnight. After cooling to room temperature, precipitates settled out, which were filtered to give the corresponding phosphine-salen type ligands and phosphine-Schiff base type ligands L1-L13 in good yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol Reflux; | General procedure of the preparation of chiral phosphine-Schiff base type ligands L1-L13 General procedure: To a solution of (R)-(-)-2-(diphenylphosphino)-1,1'-binaphthyl-2'-amine1,2 (227 mg, 0.5 mmol) in absolute ethanol (4.0 mL) was added salicylaldehydes (0.5 mmol) or its analogues (0.5 mmol) at room temperature and the reaction mixture was stirred under reflux overnight. After cooling to room temperature, precipitates settled out, which were filtered to give the corresponding phosphine-salen type ligands and phosphine-Schiff base type ligands L1-L13 in good yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In ethanol Reflux; | General procedure of the preparation of chiral phosphine-Schiff base type ligands L1-L13 General procedure: To a solution of (R)-(-)-2-(diphenylphosphino)-1,1'-binaphthyl-2'-amine1,2 (227 mg, 0.5 mmol) in absolute ethanol (4.0 mL) was added salicylaldehydes (0.5 mmol) or its analogues (0.5 mmol) at room temperature and the reaction mixture was stirred under reflux overnight. After cooling to room temperature, precipitates settled out, which were filtered to give the corresponding phosphine-salen type ligands and phosphine-Schiff base type ligands L1-L13 in good yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | In ethanol;Reflux; | General procedure: To a solution of (R)-(-)-2-(diphenylphosphino)-1,1'-binaphthyl-2'-amine1,2 (227 mg, 0.5 mmol) in absolute ethanol (4.0 mL) was added salicylaldehydes (0.5 mmol) or its analogues (0.5 mmol) at room temperature and the reaction mixture was stirred under reflux overnight. After cooling to room temperature, precipitates settled out, which were filtered to give the corresponding phosphine-salen type ligands and phosphine-Schiff base type ligands L1-L13 in good yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol Reflux; | General procedure of the preparation of chiral phosphine-Schiff base type ligands L1-L13 General procedure: To a solution of (R)-(-)-2-(diphenylphosphino)-1,1'-binaphthyl-2'-amine1,2 (227 mg, 0.5 mmol) in absolute ethanol (4.0 mL) was added salicylaldehydes (0.5 mmol) or its analogues (0.5 mmol) at room temperature and the reaction mixture was stirred under reflux overnight. After cooling to room temperature, precipitates settled out, which were filtered to give the corresponding phosphine-salen type ligands and phosphine-Schiff base type ligands L1-L13 in good yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol Reflux; | General procedure of the preparation of chiral phosphine-Schiff base type ligands L1-L13 General procedure: To a solution of (R)-(-)-2-(diphenylphosphino)-1,1'-binaphthyl-2'-amine1,2 (227 mg, 0.5 mmol) in absolute ethanol (4.0 mL) was added salicylaldehydes (0.5 mmol) or its analogues (0.5 mmol) at room temperature and the reaction mixture was stirred under reflux overnight. After cooling to room temperature, precipitates settled out, which were filtered to give the corresponding phosphine-salen type ligands and phosphine-Schiff base type ligands L1-L13 in good yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | In ethanol Reflux; | General procedure of the preparation of chiral phosphine-Schiff base type ligands L1-L13 General procedure: To a solution of (R)-(-)-2-(diphenylphosphino)-1,1'-binaphthyl-2'-amine1,2 (227 mg, 0.5 mmol) in absolute ethanol (4.0 mL) was added salicylaldehydes (0.5 mmol) or its analogues (0.5 mmol) at room temperature and the reaction mixture was stirred under reflux overnight. After cooling to room temperature, precipitates settled out, which were filtered to give the corresponding phosphine-salen type ligands and phosphine-Schiff base type ligands L1-L13 in good yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | In ethanol Reflux; | General procedure of the preparation of chiral phosphine-Schiff base type ligands L1-L13 General procedure: To a solution of (R)-(-)-2-(diphenylphosphino)-1,1'-binaphthyl-2'-amine1,2 (227 mg, 0.5 mmol) in absolute ethanol (4.0 mL) was added salicylaldehydes (0.5 mmol) or its analogues (0.5 mmol) at room temperature and the reaction mixture was stirred under reflux overnight. After cooling to room temperature, precipitates settled out, which were filtered to give the corresponding phosphine-salen type ligands and phosphine-Schiff base type ligands L1-L13 in good yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol Reflux; | General procedure of the preparation of chiral phosphine-Schiff base type ligands L1-L13 General procedure: To a solution of (R)-(-)-2-(diphenylphosphino)-1,1'-binaphthyl-2'-amine1,2 (227 mg, 0.5 mmol) in absolute ethanol (4.0 mL) was added salicylaldehydes (0.5 mmol) or its analogues (0.5 mmol) at room temperature and the reaction mixture was stirred under reflux overnight. After cooling to room temperature, precipitates settled out, which were filtered to give the corresponding phosphine-salen type ligands and phosphine-Schiff base type ligands L1-L13 in good yields. |