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CAS No. : | 931-71-5 | MDL No. : | MFCD00075462 |
Formula : | C6H12O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VKONPUDBRVKQLM-UHFFFAOYSA-N |
M.W : | 116.16 | Pubchem ID : | 11162 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H317-H319 | 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 |
---|---|---|
With potassium hydrogensulfate | ||
With magnesium sulfate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ethanol; sodium ethanolate at 30℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine | ||
With triethylamine; benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; chloroform at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; diphosphorus tetraiodide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In chloroform |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 19% 2: 43% 3: 17% 4: 11% | With tris(triphenylphosphine)ruthenium(II) chloride In dichloromethane at 50℃; for 2h; ruthenium(II) catalyzed reaction of 1,4-endoperoxide; | |
1: 17 % Chromat. 2: 11 % Chromat. 3: 43 % Chromat. 4: 19 % Spectr. | With tris(triphenylphosphine)ruthenium(II) chloride In dichloromethane at 50℃; for 2h; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 21% 2: 17% 3: 28% 4: 5% | With cobalt(II) 5,10,15,20-tetraphenylporphyrin In chloroform at 60℃; for 11h; Further byproducts given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 44 % Chromat. 2: 4 % Chromat. 3: 39 % Chromat. | With tetrakis(triphenylphosphine) palladium(0) In dichloromethane at 60℃; for 5h; other reagent; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With triethylamine In benzene at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In benzene at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride for 5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 0.5h; | ||
0.16 g | With water; triphenylphosphine In dichloromethane at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium dioxane; Yield given. Multistep reaction; | ||
Stage #1: cis-1,4-cyclohexanediol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 25℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | In benzene at 60 - 70℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanol; nickel at 150℃; Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ethanol; nickel at 100 - 200℃; Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen; nickel at 130℃; | ||
With ethanol; nickel at 130℃; Hydrogenation; | ||
With water; nickel at 115℃; Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 78 percent / triethylamine / benzene / 12 h / 20 °C 2: 88 percent / sulfur / benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / benzene / 12 h / 20 °C 2: sulfur / benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 62 percent / benzene / 6 h / 60 - 70 °C 2: 63 percent / sulfur / benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 31 percent / pyridine / 24 h / Ambient temperature 2: 6 N aq. HCl / 5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1) Na / dioxane 2: 1) NaH / 1) THF, 50-55 deg C, 2) 60 deg C, 12h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide In dimethyl sulfoxide at 50℃; for 18h; | X.18 Preparation #18. cis-4-(2-Hydroxy-2-methy-propoxy)-cyclohexanol Preparation #18. cis-4-(2-Hydroxy-2-methy-propoxy)-cyclohexanol 2,2-Dimethyl-oxirane (4.69 mL, 0.0526 mol) was added slowly to a mixture of cis-cyclohexane-1,4-diol (J. Org. Chem. 1962, 27, 4708-4709) (5.55 g, 0.0478 mol) and potassium hydroxide (3.22 g, 0.0573 mol) in dimethyl sulfoxide (50 mL). The reaction mixture was heated at about 50° C. for about 18 hours. The solvent was removed under reduced pressure. Water was added (100 mL), and the aqueous layer was extracted with diethyl ether (6*75 mL), then dichloromethane (3*100 mL). The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel using ethyl acetate/dichloromethane (1:1) as the mobile phase to afford cis-4-(2-hydroxy-2-methy-propoxy)-cyclohexanol (3.55 g, 0.0189 mol); m/z 189 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium diazodicarboxylate; acetic acid In methanol at 0℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 1.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / 0 - 20 °C 2: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / 0 - 20 °C 2: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 60 °C 3: sodium periodate; osmium(VIII) oxide / tetrahydrofuran; <i>tert</i>-butyl alcohol / 3 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / 0 - 20 °C 2: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 60 °C 3: sodium periodate; osmium(VIII) oxide / tetrahydrofuran; <i>tert</i>-butyl alcohol / 3 h / 0 - 20 °C 4: pyridine / ethanol / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / 0 - 20 °C 2: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 60 °C 3: sodium periodate; osmium(VIII) oxide / tetrahydrofuran; <i>tert</i>-butyl alcohol / 3 h / 0 - 20 °C 4: pyridine / ethanol / 1 h / 20 °C 5: 10% palladium on activated carbon; hydrogen / methanol / 4 h / 20 °C / 3000.3 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / 0 - 20 °C 2: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 60 °C 3: sodium periodate; osmium(VIII) oxide / tetrahydrofuran; <i>tert</i>-butyl alcohol / 3 h / 0 - 20 °C 4: pyridine / ethanol / 1 h / 20 °C 5: 10% palladium on activated carbon; hydrogen / methanol / 4 h / 20 °C / 3000.3 Torr 6: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 20 - 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / 0 - 20 °C 2: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 60 °C 3: sodium periodate; osmium(VIII) oxide / tetrahydrofuran; <i>tert</i>-butyl alcohol / 3 h / 0 - 20 °C 4: pyridine / ethanol / 1 h / 20 °C 5: 10% palladium on activated carbon; hydrogen / methanol / 4 h / 20 °C / 3000.3 Torr 6: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 20 - 40 °C 7: triethylamine / dichloromethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / 0 - 20 °C 2: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 60 °C 3: sodium periodate; osmium(VIII) oxide / tetrahydrofuran; <i>tert</i>-butyl alcohol / 3 h / 0 - 20 °C 4: pyridine / ethanol / 1 h / 20 °C 5: 10% palladium on activated carbon; hydrogen / methanol / 4 h / 20 °C / 3000.3 Torr 6: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 20 - 40 °C 7: triethylamine / dichloromethane / 1 h / 20 °C 8: n-heptane; isopropyl alcohol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: cis-1,4-cyclohexanediol With sodium hydride In tetrahydrofuran for 0.166667h; Stage #2: (R)-2-(2-fluoropyridin-4-yl)-8-phenyl-7,8-dihydro-6H-pyrrolo[2',1':2,3]imidazo[4,5-b]pyridine In tetrahydrofuran at 120℃; for 0.666667h; Microwave irradiation; | 47 Example 47: (i?)-8-Phenyl-2-(2-((tetrahydro-2H-pyran-4-yl)oxy)pyridin-4-yl)-7,8-dihyd pyrrolo [2',1 ' :2,3] imidazo [4,5-6] pyridine General procedure: Tetrahydro-2H-pyran-4-ol (0.046 g, 0.454 mmol) was taken into DMF (1 mL) followed by the addition of NaH (0.018 g, 0.454 mmol). The mixture was stirred for about 10 min, then (i?)-2-(2-fluoropyridin-4-yl)- 8-phenyl-7,8-dihydro-6H-pyrrolo[2', l':2,3]imidazo[4,5-6]pyridine (0.05 g, 0.151 mmol, Preparation 84) in DMF (1 mL) was added and the mixture was heated at about 120 °C for about 40 min in a microwave. The reaction was cooled to rt, a few drops of water was added, and the mixture was concentrated under reduced pressure. The residue dissolved was purified by prep-HPLC (Table 1, Method aq) to afford the product (0.02 g, 35 %); LC/MS (Table 1, Method ab) R, = 0.83 min; MS m/z: 413 (M+ H)+. (TNF IC50 = A). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: ethanol; sodium tetrahydroborate / 1.5 h / 10 °C 2: sodium hydroxide; water / ethanol / 15 h / -20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.3% | With water; sodium hydroxide In ethanol at -20℃; for 15h; | 2.1 2. Compound III-2 Preparation of Compound I Dissolve III-2 (75.8 g, 0.381 mol, 1.0 eq.) in 90% aqueous ethanol (1 L) and add at -20°C.Sodium hydroxide (30.5 g, 0.762 mol, 2.0 eq.) was added and the reaction was continued for 15 hours.The reaction mixture was purified by column chromatography (dichloromethane:methanol=10:2) to give a white solid (34.0 g, 0.344 mol). Yield: 90.3%, purity: 97%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.8% | With ammonium hydroxide; water In methanol at -20℃; for 15h; | 3.1 2. Compound III-3 Preparation of Compound I Dissolve III-3 (82.7 g, 0.526 mol, 1.0 eq.) in 90% aqueous methanol (1.6 L).Aqueous ammonia (79.0 mL, 1.05 mol, 2.0 eq.) was added at -20[deg.] C. After the addition was complete, the reaction was continued for 15 hours.Column chromatography of the reaction mixture (dichloromethane:methanol=10:2) gave a white solid (56.7 g, 0.488 mol). Yield: 92.8%, purity: 97%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / -5 °C 2: water; potassium hydroxide / tetrahydrofuran / 14 h / -20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.5% | With water; potassium hydroxide In tetrahydrofuran at -20℃; for 14h; | 4.2 2. Compound III-4 Preparation of Compound I III-4 (91.3 g, 0.417 mol, 1.0 eq.) was dissolved in 90% THF in water (1.5 L).Potassium hydroxide (46.8 g, 0.834 mol, 2.0 eq.) was added at -20[deg.] C. After the addition was complete, the reaction was continued for 14 hours.The reaction mixture was purified by column chromatography (dichloromethane:methanol=10:2) to give a white solid (43.8 g, 0.377 mol). Yield: 90.5%, purity: 97%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.9% | With water; sodium hydroxide In isopropyl alcohol at -20℃; for 12h; | 5.2 2. Compound III-5 Preparation of Compound I Dissolve III-5 (84.6 g, 0.284 mol, 1.0 eq.) in 90% aqueous isopropanol (1.0 L).Sodium hydroxide (22.7 g, 0.568 mol, 2.0 eq.) was added at -20[deg.] C. After the addition was complete, the reaction was continued for 12 hours.The reaction mixture was subjected to column chromatography (dichloromethane:methanol=10:2) to give a white solid (29.3 g, 0.252 mol). Yield: 88.9%, purity: 97%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 3.5 h / -10 °C 2: water; potassium hydroxide / tetrahydrofuran / 12 h / -20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.3% | With water; potassium hydroxide In tetrahydrofuran at -20℃; for 12h; | 6.2 2. Compound III-6 Preparation of Compound I III-6 (50.7 g, 0.296 mol, 1.0 eq.)Dissolved in 90% THF in water (1.0L)Add potassium hydroxide (33.2 g, 0.592 mol, 2.0 eq.) at -20°C,After the addition was complete, the reaction was continued for 12 hours.Column chromatography of the reaction mixture (dichloromethane:methanol=10:2) gave a white solid (31.4 g, 0.270 mol). Yield: 91.3%. Purity: 97%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: iodine; methanol; potassium borohydride / 2 h / 5 °C 2: sodium hydroxide; water / methanol / 14 h / -15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.3% | With water; sodium hydroxide In methanol at -15℃; for 14h; | 7.2 2. Compound III-7 Preparation of Compound I III-7 (73.3 g, 0.294 mol, 1.0 eq.) was dissolved in 90% aqueous methanol (1.0 L).Sodium hydroxide (23.5 g, 0.588 mol, 2.0 eq.) was added at -15[deg.] C. After the addition was complete, the reaction was continued for 14 hours.Column chromatography of the reaction mixture (dichloromethane:methanol=10:2) gave a white solid (32.2 g, 0.277 mol). Yield: 94.3%, purity: 97%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: lithium borohydride; propan-1-ol / 1 h / 15 °C 2: lithium hydroxide; water / propan-1-ol / 12 h / -10 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.8% | With water; lithium hydroxide In propan-1-ol at -10℃; for 12h; | 8.2 2. Compound III-8 Preparation of Compound I Dissolve III-8 (46.3 g, 0.176 mol, 1.0 eq.) in 90% aqueous n-propanol (0.7 L).Lithium hydroxide (8.43 g, 0.352 mol, 2.0 eq.) was added at -10[deg.] C. After the addition was complete, the reaction was continued for 12 hours.Column chromatography of the reaction mixture (dichloromethane:methanol=10:2) gave a white solid (16.7 g, 0.144 mol). Yield: 81.8%, purity: 97%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; isopropyl alcohol / 1.5 h / 10 °C 2: sodium hydroxide; water / isopropyl alcohol / 13 h / -10 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.6% | With water; sodium hydroxide In isopropyl alcohol at -10℃; for 13h; | 9.2 2. Compound III-9 Preparation of Compound I Dissolve III-9 (48.6 g, 0.184 mol, 1.0 eq.) in 90% aqueous isopropanol (0.8 L).Sodium hydroxide (14.7 g, 0.368 mol, 2.0 eq.) was added at -10[deg.] C. After the addition was complete, the reaction was continued for 13 hours.Column chromatography of the reaction mixture (dichloromethane:methanol=10:2) gave a white solid (16.2 g, 0.139 mol). Yield: 75.6%, purity: 97%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: ethanol; potassium borohydride / 3 h / -5 °C 2: lithium hydroxide; water / ethanol / 10 h / -5 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.2% | With water; lithium hydroxide In ethanol at -5℃; for 10h; | 10.2 2. Compound III-10 Preparation of Compound I Dissolve III-10 (93.1 g, 0.377 mol, 1.0 eq.) in 90% aqueous ethanol (1.0 L) and add at -5°C.Lithium hydroxide (18.1 g, 0.754 mol, 2.0 eq.) was added and the reaction was continued for 10 hours.Column chromatography of the reaction mixture (dichloromethane:methanol = 10:2) gave a white solid (41.3 g, 0.355 mol).Yield: 94.2%, purity: 97%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / -15 °C 2: sodium hydroxide; water / tetrahydrofuran / 12 h / -10 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.6% | With water; sodium hydroxide In tetrahydrofuran at -10℃; for 12h; | 11.2 2. Compound III-11 Preparation of Compound I III-11 (37.2 g, 0.119 mol, 1.0 eq.) was dissolved in 90% aqueous THF (0.5 L).Sodium hydroxide (9.52 g, 0.238 mol, 2.0 eq.) was added at -10[deg.] C. After the addition was complete, the reaction was continued for 12 hours.The reaction mixture was subjected to column chromatography (dichloromethane:methanol=10:2) to give a white solid (12.8 g, 0.110 mol). Yield: 92.6%, purity: 97%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: methanol; potassium borohydride / 4 h / -15 °C 2: water; potassium hydroxide / methanol / 12 h / -15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: lithium chloride; methanol; potassium borohydride / 2.5 h / 0 °C 2: water; potassium hydroxide / methanol / 14 h / -15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.8% | With water; potassium hydroxide In methanol at -15℃; for 14h; | 12.2 2. Compound III-12 Preparation of Compound I III-12 (60.6 g, 0.239 mol, 1.0 eq.) was dissolved in 90% aqueous methanol (0.8 L).Potassium hydroxide (26.8 g, 0.478 mol, 2.0 eq.) was added at -15[deg.] C. After the addition was complete, the reaction was continued for 14 hours.Reaction liquid chromatography (dichloromethane:methanol=10:2) gave a white solid (25.5 g, 0.219 mol). Yield: 91.8%, purity: 97%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / 5 °C 2: sodium hydroxide; water / tetrahydrofuran / 12 h / -10 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.1% | With water; sodium hydroxide In tetrahydrofuran at -10℃; for 12h; | 13.2 2. Compound III-13 Preparation of Compound I Dissolve III-13 (107.3 g, 0.401, 1.0 eq.) in 90% aqueous THF (1.0 L).-10°C addedSodium hydroxide(32.1 g, 0.802 mol, 2.0 eq.),After the addition was complete, the reaction was continued for 12 hours.The reaction mixture was subjected to column chromatography (dichloromethane:methanol=10:2) to give a white solid (43.3 g, 0.372 mol). Yield: 93.1%, purity: 97%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.7% | With water; potassium hydroxide In methanol at -15℃; for 12h; | 1.2 2. Compound III-1 Preparation of Compound I Dissolve III-1 (68.5 g, 0.30 mol, 1.0 eq.) in 90% aqueous methanol (0.8 L) and add at -15°C.Potassium hydroxide (33.7 g, 0.60 mol, 2.0 eq.) was added and the reaction was continued for 12 hours.Column chromatography (dichloromethane:methanol = 10:2) gave a white solid (31.9 g, 0.275 mol).Yield: 91.7%, purity: 97%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7.57% | With pyridine In dichloromethane at 0 - 20℃; for 2h; | 8 To a solution of compound 8.1 (500 mg, 4.30 mmol, 1 equiv) in dichloromethane (50 mL) was added pyridine (818 mg, 10.33 mmol, 833.84 pL, 2.4 equiv) in one portion at 0 °C. After that, a solution of compound 8.2 (1.91 g, 9.47 mmol, 823.92 pL, 2.2 equiv) in dichloromethane (50 mL) was added dropwise to the mixture at 0 °C. After the addition was complete, the reaction mixture was stirred at 20 °C for 2 hr. TLC (petroleum ether/ethyl acetate = 0/1) showed compound 8.1 was all consumed (Rf = 0.35); no new spot was detected. The reaction mixture was diluted with water (50 mL) and extracted with EtOAc (30 mL x 3). The combined organic phases were dried over Na2S04, filtered, and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (S1O2, petroleum ether/ethyl acetate = 30/1 to about 20/1) to give Linker 15b (120 mg, 326.00 pmol, 7.57% yield, 97.2633% GC purity) as a colorless oil. NMR (400 MHz CDCh): d 4.94 (br s, 2H), 3.84 (s, 4H), 1.96 - 1.83 (m, 4H), 1.82 - 1.70 (m, 4H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 12 h / 25 °C 2.1: triethylamine / dichloromethane / 7 h / 0 - 25 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 12 h / 25 °C 2.1: triethylamine / dichloromethane / 7 h / 0 - 25 °C / Inert atmosphere 3.1: caesium carbonate / N,N-dimethyl acetamide / 12 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 12 h / 25 °C 2.1: triethylamine / dichloromethane / 7 h / 0 - 25 °C / Inert atmosphere 3.1: caesium carbonate / N,N-dimethyl acetamide / 12 h / 120 °C 4.1: boron trichloride / dichloromethane / 2.5 h / -78 - 25 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride In N,N-dimethyl acetamide at 20℃; |
Tags: 931-71-5 synthesis path| 931-71-5 SDS| 931-71-5 COA| 931-71-5 purity| 931-71-5 application| 931-71-5 NMR| 931-71-5 COA| 931-71-5 structure
[ 60662-54-6 ]
(1α,3α,5α)-Cyclohexane-1,3,5-triol dihydrate
Similarity: 0.92
[ 13314-30-2 ]
1α,3α,5β-Trihydroxycyclohexane
Similarity: 0.92
[ 60662-54-6 ]
(1α,3α,5α)-Cyclohexane-1,3,5-triol dihydrate
Similarity: 0.92
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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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