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CAS No. : | 1219025-18-9 | MDL No. : | |
Formula : | C45H58NP | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 643.92 | 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 |
---|---|---|
91% | Stage #1: C46H57O2P With sodium azide; sulfuric acid In chloroform at 40℃; for 5.5h; Reflux; Stage #2: With water; sodium hydroxide In chloroform at 0℃; | |
With sodium azide; sulfuric acid In chloroform Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; Inert atmosphere; | |
92% | With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 6h; Inert atmosphere; | 1 Example 1: Synthesis of (R)-N-(pyridyl-2-methyl)-7-di-(3,5-di-tert-butylphenyl)phosphino-7-amino-1,1'-spiro-dihydro-indene (Ia) Example 1 Synthesis of (R)-N-(pyridyl-2-methyl)-7-di-(3,5-di-tert-butylphenyl)phosphino-7-amino-1,1'-spiro-dihydro-indene (Ia) Under nitrogen atmosphere, (R)-7-di-(3,5-di-tert-butylphenyl)phosphino-7'-amino-1,1'-spiro-dihydro-indene (966 mg, 1.5 mmol), sodium triacetoxyborohydride (509 mg, 2.4 mmol) and 6 ml 1,2-dichloroethane were weighed into a 50 ml dry two-neck bottle. After the solid was dissolved by stirring at room temperature, pyridylaldehyde was added (161 mg, 1.5 mmol). After the reaction was stirred for 6 h at room temperature, the starting material was almost consumed (monitored by TLC, petroleum ether : ethyl acetate = 7:1). The reaction was quenched by saturated aqueous solution of sodium bicarbonate, extracted by ethyl acetate, and dried by anhydrous magnesium sulfate. After desolventization, 1.01 g white solid was obtained by purification of the resulting solid through silica gel column chromatography (petroleum ether : ethyl acetate = 10:1, 2% triethylamine), with a yield of 92%. Mp 172-174 °c; [α]20,D +172 (c 0.5, CH2Cl2); 1H NMR (400 mhz, cdcl3) δ 8.30 (d, J= 4.8 Hz, 1H, Ar-H), 7.44-7.39 (m, 1H, Ar-H), 7.31 (d, J = 7.2 Hz, 1H, Ar-H), 7.26-7.19 (m, 3H, Ar-H), 7.12-7.06 (m, 2H, Ar-H), 7.02-6.99 (m, 1H, Ar-H), 6.88-6.84 (m, 3H, Ar-H), 6.77-6.75 (dd, J= 1.6, 7.6 Hz, 2H, Ar-H), 6.68 (d, J= 9.2 Hz, 1H, Ar-H), 6.10 (d, J = 8.0 Hz, 1H, Ar-H), 4.20 (t, J = 5.2 Hz, 1H), 3.97 (dd, J = 6, 16.4 Hz, 1H), 3.73 (dd, J = 4.4, 16.4 Hz, 1H), 3.13-2.76 (m, 4H), 2.49-2.40(m, 1H), 2.19-2.09 (m, 3H), 1.09 (s, 18H), 1.16 (s, 18H); 31P NMR (162 mhz, cdcl3) δ -18.17 (s); 13C NMR (100 mhz, cdcl3) δ 155.8, 152.5 (d, J = 24.3 Hz), 149.9 (d, J = 6.3 Hz), 148.9, 144.3, 144.2, 144.1, 138.2 (d, J= 11.7 Hz), 136.1, 135.2, 134.9, 133.8, 132.6 (d, J= 3.4 Hz), 128.4, 128.1, 128.0, 127.9, 126. 9, 125.7, 122.2, 121.5, 121.5, 120.7, 113.9, 108.6, 61.7 (d, J = 3.3 Hz), 48.5, 38.6 (d, J = 3.4 Hz), 36.1, 34.7 (d, J = 3.8 Hz), 31.4 (d, J = 2.4 Hz), 30.92, 31.36. HRMS (ESI) calcd for C51H63N2P[M + H]+: 735.4802; Found: 735.4804. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridine / toluene / 0 - 20 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: pyridine / toluene / 0 - 20 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux 3: pyridine / toluene / 0 - 20 °C / Inert atmosphere 4: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: pyridine / toluene / 0 - 20 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux 3: pyridine / toluene / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In toluene at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hydrogen; Pd/C / ethanol / 4 h / 20 °C 2: indium(III) chloride / 1,2-dichloro-ethane / 2 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With Pd/C; hydrogen In ethanol at 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetic acid / methanol; toluene / 5 h / 20 °C / Inert atmosphere 1.2: 12 h / 40 °C / Inert atmosphere 2.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 12 h / 80 °C / Sealed tube 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 12 h / 20 °C / Inert atmosphere 4.1: triethylamine; dmap; methanesulfonyl chloride / dichloromethane / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetic acid / methanol; toluene / 5 h / 20 °C / Inert atmosphere 1.2: 12 h / 40 °C / Inert atmosphere 2.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 12 h / 80 °C / Sealed tube 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 12 h / 20 °C / Inert atmosphere 4.1: triethylamine; dmap; methanesulfonyl chloride / dichloromethane / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetic acid / methanol; toluene / 5 h / 20 °C / Inert atmosphere 1.2: 12 h / 40 °C / Inert atmosphere 2.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 12 h / 80 °C / Sealed tube 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 12 h / 20 °C / Inert atmosphere 4.1: triethylamine; dmap; methanesulfonyl chloride / dichloromethane / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetic acid / methanol; toluene / 5 h / 20 °C / Inert atmosphere 1.2: 12 h / 40 °C / Inert atmosphere 2.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 12 h / 80 °C / Sealed tube 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 12 h / 20 °C / Inert atmosphere 4.1: triethylamine; dmap; methanesulfonyl chloride / dichloromethane / 0 - 20 °C |
A1175269[ 1287372-60-4 ]
(S)-7'-(Bis(3,5-di-tert-butylphenyl)phosphanyl)-2,2',3,3'-tetrahydro-1,1'-spirobi[inden]-7-amine
Reason: Optical isomers