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CAS No. : | 1210-34-0 | MDL No. : | MFCD00003593 |
Formula : | C15H14O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | POAVRNPUPPJLKZ-UHFFFAOYSA-N |
M.W : | 210.27 | Pubchem ID : | 14588 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 64.87 |
TPSA : | 20.23 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.43 cm/s |
Log Po/w (iLOGP) : | 2.32 |
Log Po/w (XLOGP3) : | 3.03 |
Log Po/w (WLOGP) : | 2.54 |
Log Po/w (MLOGP) : | 3.2 |
Log Po/w (SILICOS-IT) : | 3.55 |
Consensus Log Po/w : | 2.93 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.61 |
Solubility : | 0.0519 mg/ml ; 0.000247 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.12 |
Solubility : | 0.159 mg/ml ; 0.000758 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.95 |
Solubility : | 0.00239 mg/ml ; 0.0000114 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.02 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-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 |
---|---|---|
97% | With dichlorosulfoxide; N,N-dimethyl-formamide In diethyl ether at 0 - 20℃; Inert atmosphere; | |
93% | With hydrogenchloride; calcium(II) chloride In benzene for 2.5h; | |
60% | With hydrogenchloride In diethyl ether at 20℃; for 0.5h; |
60% | With hydrogenchloride In diethyl ether; lithium hydroxide monohydrate at 20℃; for 1.5h; | 30 20.02 g (0.95 mol) of 10,11-dihydro-5H-dibenzocyclohepten-5-ol was dissolved in 200 ml of diethyl ether, and hydrogen chloride gas was stirred at room temperature. After 1.5 hours, the reaction was stopped, After a white solid, petroleum ether recrystallization, needle-like white solid 12.61g, mp 1010-105 ° C, yield 60% |
With pyridine; dichlorosulfoxide; benzene | ||
With hydrogenchloride In diethyl ether | ||
With hydrogenchloride In benzene | ||
With hydrogenchloride In toluene | ||
With dichlorosulfoxide | ||
With dichlorosulfoxide In benzene | 1.b Preparation of 1-[2-(4,5,10,11-tetrahydro-1H-dibenzo[a,d]cyclohepten-5-yl)ethyl]pyrrolidine (b) 350 ml of thionyl chloride are added dropwise at a temperature of 30 to 40° to a solution of 201.5 g of crude 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol in 700 ml of dry benzene over a period of 40 minutes. Subsequently, the mixture is heated to boiling under reflux for an additional 1.5 hours and concentrated in vacuo. The residue is diluted 2 to 3 times with 300 ml of benzene each time and in each case again evaporated. There is obtained 5-chloro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene as a beige crystalline mass of melting point 99-101° which is used in the next step without further purification. By recrystallization from carbon tetrachloride there is obtained material of melting point 104°-105° C. | |
With dichlorosulfoxide In dichloromethane at 0 - 20℃; for 1h; | ||
105 g | With dichlorosulfoxide In dichloromethane at 0 - 30℃; for 12h; | 1 Compound 1b (100g, 476mmol, 1.00eq) was dissolved in a reaction flask with dichloromethane (1L), cooled to 0-5°C, SOCl2 (113g, 951mmol, 69.0mL, 2.00eq) was added to the reaction system, the material After the addition, the system was stirred at 20-30°C for 12 hours. Without detection, the reaction solution was concentrated, washed with petroleum ether (200 mL) after concentration, filtered, and the filter cake was concentrated to obtain compound 1c (105 g, 459 mmol, 96.5% yield, pink solid, structure confirmed by NMR). |
1.05 g | With dichlorosulfoxide In dichloromethane at 20℃; | 17 In the reaction flask, compound 17b (1.02 g, 4.85 mmol) and 1M SOCl2-CH2Cl2 solution (10 mL) were added in sequence, stirred at room temperature overnight, TLC showed that the reaction was complete, and concentrated to dryness under reduced pressure to obtain compound 171.05 as a dark green oil. g, the crude product was directly used in the next reaction without purification. |
With dichlorosulfoxide In dichloromethane at 20℃; | 17 In the reaction flask, compound 17b (1.02 g, 4.85 mmol) and 1M SOCl2-CH2Cl2 solution (10 mL) were added in sequence, stirred at room temperature overnight, TLC showed that the reaction was complete, and concentrated to dryness under reduced pressure to obtain compound 171.05 as a dark green oil. g, the crude product was directly used in the next reaction without purification. | |
With dichlorosulfoxide In dichloromethane at 20℃; | In the reaction flask, compound 17b (1.02 g, 4.85 mmol) and 1M SOCl2-CH2Cl2 solution (10 mL) were added in sequence, and stirred overnight at room temperature. TLC showed that the reaction was complete. It was concentrated to dryness under reduced pressure to obtain 171.05 g of a dark green oily compound, and the crude product was directly used in the next reaction without purification. | |
105 g | With dichlorosulfoxide In dichloromethane at 0 - 30℃; for 12h; | 1 Compound 1b (100g, 476mmol, 1.00eq) was dissolved in a reaction flask with dichloromethane (1L), cooled to 0-5°C, SOCl2 (113g, 951mmol, 69.0mL, 2.00eq) was added to the reaction system, the material After the addition, the system was stirred at 20-30°C for 12 hours. Without detection, the reaction solution was concentrated, washed with petroleum ether (200 mL) after concentration, filtered, and the filter cake was concentrated to obtain compound 1c (105 g, 459 mmol, 96.5% yield, pink solid, structure confirmed by NMR).Remarks: Because the activity of the product is too high, it can be decomposed in the presence of water, and neither TLC or LCMS can display the product well. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With dimethylsilicon dichloride; sodium iodide In dichloromethane; acetone for 0.166667h; Ambient temperature; | |
With sodium formate In formic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With potassium carbonate; In n-heptane; at 80℃; under 750.075 Torr; for 24h; | General procedure: A magnetic stir bar, 0.5 mmol alcohol and 3 mL n-heptane solvent were added to 20 mL glass tube. Then, 35mg catalyst and 10 mol% of K2CO3 were added. The glass tube containing reaction mixture was f itted withseptum and connected to a balloon containing one bar of air. Then the glass tube was placed into a preheatedaluminum block at 85C. Temperature inside the reaction tube was measured to be 80 oC and this temperaturehas been taken as the reaction temperature. The reaction was allowed to progress under continuous stirringfor the required time at 80 C. Af ter completion of the reaction, the glass tube was cooled down to roomtemperature. Afterwards, the catalyst was f iltered-off and washed with ethyl acetate. The solvent f rom thef iltrate containing the reaction products was removed in vacuum and the corresponding aldehyde/ketone waspurif ied by column chromatography. All products were analyzed by GC-MS and NMR spectroscopy analysis.In the case of yields determined the by GC, 100 μL n-hexadecane was added to the reaction vial containingthe products and diluted with ethyl acetate. Then, the reaction mixture containing catalyst and products wasf iltered through a plug of silica and the filtrate containing product was analyzed by GC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 10% 2: 64% | With sodium hydroxide; di(rhodium)tetracarbonyl dichloride; N-benzyl-N,N,N-triethylammonium chloride In benzene at 55℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With iodine In dichloromethane at 25℃; for 0.166667h; | |
64% | With diethylamino-sulfur trifluoride In dichloromethane at -30℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With zinc(II) chloride In acetic acid for 3h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With zinc(II) chloride In acetic acid for 6h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With Acetyl bromide for 0.333333h; Heating; | |
With phosphorus tribromide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With acetic acid at 20℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With acetic acid at 20℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With dichloro-acetic acid; hydroxylamine hydrochloride; sodium acetate In dichloromethane at 20℃; for 20h; | |
With dichloro-acetic acid; hydroxylamine hydrochloride; sodium acetate In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: AcONa; CHCl2COOH; NH2OH*HCl / CH2Cl2 / 20 °C 2: 49 percent / CH2Cl2 / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium hydroxide In methanol; ethanol; chloroform; water; pyrographite | 1.a Preparation of 1-[2-(4,5,10,11-tetrahydro-1H-dibenzo[a,d]cyclohepten-5-yl)ethyl]pyrrolidine (a) A mixture of 208 g of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one, 2 l of ethanol, 200 g of sodium hydroxide and 300 g of zinc powder is heated to boiling under reflux while stirring for 2 hours. The still warm mixture is filtered over kieselguhr while back-washing with about 1 l of methanol. After concentration of the yellow solution to about 1 l, the thick paste obtained is partitioned between 2 l of chloroform and 1 l of water. The alkaline-aqueous phase is adjusted to pH 3 to 4 with about 400 ml of concentrated hydrochloric acid while cooling with ice and extracted with 1 l of chloroform. The combined chloroform extracts are washed with water until they are neutral and subsequently dried over magnesium sulfate in the presence of a small amount of active carbon. After filtration and concentration of the clear, light yellowish solution, there is obtained 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol as an almost white, crystalline mass with a melting point of 89-91°. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With iron(III) chloride hexahydrate In dichloromethane at 50℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With iron(III) chloride hexahydrate In dichloromethane at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With iron(III) chloride hexahydrate; toluene-4-sulfonic acid In dichloromethane at 45℃; for 5h; stereospecific reaction; | |
65% | With N-octadecyl-N-(4-sulfobutyl)pyrrolidinium trifluoromethanesulfonate In dichloromethane at 80℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With iron(III) chloride hexahydrate; toluene-4-sulfonic acid In dichloromethane at 45℃; for 5.5h; stereospecific reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With iron(III) chloride hexahydrate; toluene-4-sulfonic acid In dichloromethane at 45℃; for 5h; stereospecific reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 64% 2: 37% | With H-ZSM-5 β mesoporous zeolite at 300℃; Inert atmosphere; Pyrolysis; | |
Multi-step reaction with 3 steps 1: quartz / 350 - 650 °C / Inert atmosphere; Pyrolysis 2: sodium tetrahydroborate; sodium hydroxide / methanol 3: H-ZSM-5 β mesoporous zeolite / 300 °C / Inert atmosphere; Pyrolysis |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iodine; iron; sodium iodide In ethylene dibromide at 55℃; optical yield given as %de; | 2. General Procedure for the Synthesis of Alkenyl iodides General procedure: To a stirred solution of iron powder (0.5 mmol), iodine (0.5 mmol), sodium iodide (1.0 mmol) and alcohol (0.5 mmol) in DBE (1.0 mL) was added alkyne (1.5 mmol). The mixture was heated at 55°C and stirred for 8-12 h. Upon completion of the reaction, the mixture was filtered through a short column of silica gel and washed with ethyl acetate, and the solvents were removed by rotary evaporation to provide raw product. Then the product was purified on silica gel to afford the desired product. | |
84 % de | With indium (III) iodide; hydrogen iodide In water; ethylene dibromide at 60℃; for 6h; Inert atmosphere; Overall yield = 91 %; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With iodine In neat (no solvent) at 85℃; for 0.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65 mg | With sulfuric acid; acetic acid at 20℃; for 0.5h; | 511.3 To an acetic acid (2 ml) solution of compound 511C (130 mg, 0.350 mmol) and dibenzosuberol (368 mg, 1.75 mmol) was added dropwise sulfuric acid (0.4 ml) at room temperature, and the mixture was stirred at the same temperature for 30 minutes. The reaction solution was diluted with water, and the mixture was extracted with ethyl acetate three times. The extract was washed with water once, and dried with sodium sulfate, thereafter, the solvent was distilled off, and the resulting solid was washed with diisopropyl ether to obtain 65 mg of compound 511 as a solid. [2371] 1H-NMR (CDCl3) δ: 1.27 (3H, d, J=6.9 Hz), 1.49 (3H, d, J=6.6 Hz), 1.64-1.74 (1H, m), 1.88-1.99 (1H, m), 2.83 (1H, d, J=4.5 Hz, 4.5 Hz, 9.3 Hz), 3.06 (1H, ddd, J=5.6 Hz, 13.2 Hz, 13.2 Hz), 3.19 (3H, s), 3.30-3.44 (1H, m), 3.50-3.57 (1H, m), 3.78-3.92 (1H, m), 4.28 (1H, ddd, J=4.2 Hz, 13.5 Hz, 13.5 Hz), 4.53 (1H, dd, J=3.3 Hz, 10.8 Hz), 4.96 (1H, s), 5.73 (1H, d, J=7.5 Hz), 6.61 (1H, d, J=7.5 Hz), 6.65 (1H, d, J=7.5 Hz), 6.89-6.93 (1H, m), 7.08-7.36 (6H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone for 3h; Reflux; | The synthesis of the S-thiocarbamates 8a-c General procedure: To the solution of aroylisothiocyanates 5a-c obtained in the previous step were added 5 mmol of ananhydrous acetone solution of 5-dibenzosuberol. The reactionmixture was heated under reflux for 3 h and then evaporated to dryness invacuum. The final compounds 8a-cwere crystallized from isopropanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone for 3h; Reflux; | The synthesis of the S-thiocarbamates 8a-c General procedure: To the solution of aroylisothiocyanates 5a-c obtained in the previous step were added 5 mmol of ananhydrous acetone solution of 5-dibenzosuberol. The reactionmixture was heated under reflux for 3 h and then evaporated to dryness invacuum. The final compounds 8a-cwere crystallized from isopropanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone for 3h; Reflux; | The synthesis of the S-thiocarbamates 8a-c General procedure: To the solution of aroylisothiocyanates 5a-c obtained in the previous step were added 5 mmol of ananhydrous acetone solution of 5-dibenzosuberol. The reactionmixture was heated under reflux for 3 h and then evaporated to dryness invacuum. The final compounds 8a-cwere crystallized from isopropanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With boron trifluoride diethyl etherate In acetonitrile at 20℃; for 0.5h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.67 g | Stage #1: dibenzosuberol With sodium hydride In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; Stage #2: C11H13ClFN In dimethyl sulfoxide at 100℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82 % de | With hydrogenchloride; iron In chloroform; water at 55℃; Overall yield = 83 %; | 4.2 General experimental procedure General procedure: To a stirred mixture of alcohol (2.0 mmol), alkyne (2.4 mmol), and Fe powder (1 mol%) in chloroform (1 mL) was added hydrohalide (2.4 mmol). The reaction mixture was stirred vigorously at 55°C overnight. Upon completion of the reaction, the mixture was extracted with dichloromethane, dried and concentrated in vacuo to provide raw product. Then the residue was purified by silica-gel (100-200 mesh) column chromatography using petroleum ether as the eluent to obtain a mixture of E and Z isomers of desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70 % de | With hydrogen bromide; iron In chloroform; water at 55℃; Overall yield = 78 %; | 4.2 General experimental procedure General procedure: To a stirred mixture of alcohol (2.0 mmol), alkyne (2.4 mmol), and Fe powder (1 mol%) in chloroform (1 mL) was added hydrohalide (2.4 mmol). The reaction mixture was stirred vigorously at 55°C overnight. Upon completion of the reaction, the mixture was extracted with dichloromethane, dried and concentrated in vacuo to provide raw product. Then the residue was purified by silica-gel (100-200 mesh) column chromatography using petroleum ether as the eluent to obtain a mixture of E and Z isomers of desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With iron(III) trifluoromethanesulfonate; trifluorormethanesulfonic acid In nitromethane at 70℃; for 12h; Inert atmosphere; Green chemistry; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate for 0.5h; Reflux; | 2.4 Fourth step Compound 14 (1.70 g, 5.12 mmol),Suspend in ethyl acetate (10 ml),T3P (50% by weight ethyl acetate solution)(1.48 g, 10.24 mmol),Dibenzosuberol (366 mg, 1.74 mmol)Was added and heated to reflux for 30 minutes.After letting the reaction solution cool,Water was added and extracted with ethyl acetate.The resulting organic layer is dried over sodium sulfate,The solvent was distilled off under reduced pressure.The precipitated solid is suspended in ethyl acetate, collected by filtration and dried.Compound 15 (581 mg, 93%) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen In methanol at 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79.7% | With hydrogenchloride; zinc(II) chloride In water at 90 - 160℃; for 2h; | 1 Example 1 Put A (1.53g, 14.3mmol) and B (6.00g, 28.5mmol) in a 100mL flask, and after melting at 90 °C, While stirring, add dropwise a concentrated hydrochloric acid solution of ZnCl2 (ZnCl2: 0.98g, 7.2mmol, concentrated hydrochloric acid: 3.33mL, 40.0mmol). After the addition is complete, the temperature is raised to 160 °C, and the reaction is stopped after stirring for 2h. Cool to room temperature, add ethyl acetate to dissolve, wash with NaOH aqueous solution three times, and distilled water three times, separate the organic layer, dry with anhydrous Na2SO4,The solvent was evacuated to dryness to obtain the crude product, which was further purified by column chromatography (dichloromethane/petroleum ether = 2:1) to obtain pure product C (5.60 g, 79.7% yield) |
69.6% | Stage #1: <i>p</i>-toluidine; dibenzosuberol at 95℃; Stage #2: With hydrogenchloride; zinc(II) chloride In water at 160℃; | |
With hydrogenchloride; zinc(II) chloride |
With hydrogenchloride; zinc(II) chloride In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.9% | With hydrogenchloride; zinc(II) chloride In water at 95 - 160℃; for 1.5h; | 3 Example 1 General procedure: Put A (1.53g, 14.3mmol) and B (6.00g, 28.5mmol) in a 100mL flask, and after melting at 90 °C, While stirring, add dropwise a concentrated hydrochloric acid solution of ZnCl2 (ZnCl2: 0.98g, 7.2mmol, concentrated hydrochloric acid: 3.33mL, 40.0mmol). After the addition is complete, the temperature is raised to 160 °C, and the reaction is stopped after stirring for 2h. Cool to room temperature, add ethyl acetate to dissolve, wash with NaOH aqueous solution three times, and distilled water three times, separate the organic layer, dry with anhydrous Na2SO4,The solvent was evacuated to dryness to obtain the crude product, which was further purified by column chromatography (dichloromethane/petroleum ether = 2:1) to obtain pure product C (5.60 g, 79.7% yield) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: zinc(II) chloride; hydrogenchloride 2: acetic acid 3: potassium oxalate / dichloromethane; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: zinc(II) chloride; hydrogenchloride 2: acetic acid 3: potassium oxalate / dichloromethane; water 4: dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: zinc(II) chloride; hydrogenchloride 2: acetic acid 3: potassium oxalate / dichloromethane; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: zinc(II) chloride; hydrogenchloride 2: acetic acid 3: potassium oxalate / dichloromethane; water 4: dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.9% | With stannic bromide In dichloromethane at 20℃; for 12h; Inert atmosphere; | 2.4 (4) Preparation of compound 4 Under nitrogen atmosphere, Respectively 20.57g (0.08mol, 1.0eq.) compound 3 And 20.19g dibenzocycloheptanol (0.096mol, 1.2eq.) dissolved in 150mL ultra-dry dichloromethane, Slowly add 1.76g tin tetrabromide (0.004mol, 0.05eq.), Stir at room temperature for 12h. The reaction was quenched by adding 10 mL saturated aqueous sodium bicarbonate solution, Extract with dichloromethane, wash with saturated brine, combine the organic phases and dry with anhydrous sodium sulfate. The filtrate was concentrated and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 250:1 (v/v)), 31.60 g of white solid was obtained with a yield of 87.9%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With 1,1,1,3',3',3'-hexafluoro-propanol In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: anhydrous zinc chloride; hydrogenchloride / lithium hydroxide monohydrate / 3 h / 100 - 160 °C 2: toluene-4-sulfonic acid / methanol / 72 h / 100 °C / Sealed tube | ||
Multi-step reaction with 2 steps 1: hydrogenchloride; anhydrous zinc chloride / 160 °C 2: toluene-4-sulfonic acid / methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.1% | With hydrogenchloride; anhydrous zinc chloride In lithium hydroxide monohydrate at 100 - 160℃; for 3h; | 1 Example 1 Preparation of sandwich-type large hindered amine Put A (6.8g, 32.3mmol) and B (4.0g, 16.2mmol) in a 100mL flask. After melting at 100°C, add ZnCl2 concentrated hydrochloric acid solution (ZnCl2: 1.1g, 8.1mmol, concentrated hydrochloric acid: 1.35mL, 16.2mmol). After the dropwise addition is completed, the temperature is raised to 160°C, the reaction is stopped after stirring for 3h, cooled to room temperature, dissolved in dichloromethane, washed with NaOH aqueous solution three times, and distilled water three times, and the organic layer is separated , Dry with anhydrous Na2SO4, and vacuum the solvent to obtain product C (9.6 g, 94.1% yield). |
With hydrogenchloride; anhydrous zinc chloride at 160℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.3% | With hydrogenchloride; anhydrous zinc chloride In lithium hydroxide monohydrate at 100 - 160℃; for 3h; | 2 Example 2 Preparation of sandwich-type large hindered amine Put A (4.0g, 19.0mmol) and D (3.4g, 9.5mmol) in a 100mL flask, and after melting at 100°C, add ZnCl2 concentrated hydrochloric acid solution (ZnCl2: 0.65g, 4.8mmol, Concentrated hydrochloric acid: 0.8mL, 9.5mmol). After the dropwise addition is completed, the temperature is raised to 160°C, the reaction is stopped after stirring for 3 hours, cooled to room temperature, and dichloromethane is added to dissolve, washed with NaOH aqueous solution three times, and distilled water three times, and the organic layer is separated , Dry with anhydrous Na2SO4, and vacuum the solvent to obtain product E (6.0 g, 85.3% yield). |
85.3% | Stage #1: 8-(3,5-bis(trifluoromethyl)phenyl)naphthalen-1-amine; 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol at 100℃; Stage #2: With hydrogenchloride; anhydrous zinc chloride In lithium hydroxide monohydrate at 160℃; for 1.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: zinc(II) chloride; hydrogenchloride 2: toluene-4-sulfonic acid / methanol / 48 h / 80 °C / Sealed tube; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: zinc(II) chloride; hydrogenchloride 2: toluene-4-sulfonic acid / methanol / Schlenk technique; Inert atmosphere 3: diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: zinc(II) chloride; hydrogenchloride 2: toluene-4-sulfonic acid / methanol / Schlenk technique; Inert atmosphere 3: diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: zinc(II) chloride; hydrogenchloride 2: toluene-4-sulfonic acid / methanol / Schlenk technique; Inert atmosphere 3: diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With hydrogenchloride; zinc(II) chloride In water at 120 - 160℃; for 0.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; dichlorosulfoxide / diethyl ether / 0 - 20 °C / Inert atmosphere 2: indium(III) trichloride / ethyl acetate / 6 h / 0 °C / Inert atmosphere |
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Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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