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CAS No. : | 17454-47-6 | MDL No. : | MFCD00068674 |
Formula : | C18H22O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 318.36 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
58% | With PPA at 60℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With PPA at 60℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 14% 2: 38% | With nitric acid In chloroform; acetic acid Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With PPA at 60℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran for 0.25h; selectivity of reductive cleavage of the aryl-oxygen bonds; also for other arenocrown ethers; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2,3-Dihydroxy-naphthalin, 1,11-Dichlor-3,6,9-trioxaundecan; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; hydrogen bromide; zinc 1) glacial acetic acid, 5 deg C, 3 d; 2) acetic acid, r.t., 1 d; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 42% 2: 10% 3: 8% | With trichlorophosphate | |
1: 42% 2: 10% 3: 8% | With trichlorophosphate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 10 percent / POCl3 2: 64 percent / Bu4NOH / ethanol / 3 h / Heating | ||
Multi-step reaction with 2 steps 1: trichlorophosphate 2: tetra(n-butyl)ammonium hydroxide / ethanol / 3 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 8 percent / POCl3 2: 56 percent / Bu4NOH / ethanol / 3 h / Heating | ||
Multi-step reaction with 2 steps 1: trichlorophosphate 2: tetra(n-butyl)ammonium hydroxide / ethanol / 3 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 42 percent / POCl3 2: 64 percent / Bu4NOH / ethanol / 3 h / Heating | ||
Multi-step reaction with 2 steps 1: trichlorophosphate 2: tetra(n-butyl)ammonium hydroxide / ethanol / 3 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: conc. HCl / CH2Cl2; methanol / 1 h / Ambient temperature 2: 90 percent / NaOH, p-toluenesulfonyl chloride / dioxane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: NaOH / butan-1-ol / 30 h / Heating 2: conc. HCl / CH2Cl2; methanol / 1 h / Ambient temperature 3: 90 percent / NaOH, p-toluenesulfonyl chloride / dioxane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | In water; 1,2-dichloro-ethane aq. mixt. of Na2PtCl4 and NaSCN was added to a soln. of crown ether in 1,2-dichloroethane, the mixt. was stired for 2 h at room temp.; the organic phase was sepd., crystd. from diethyl ether-1,2-dichloroethane (4:1); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In water; 1,2-dichloro-ethane aq. mixt. of PdCl2 and NaSCN was added to a soln. of crown ether in 1,2-dichloroethane, the mixt. was stired for 2 h at room temp.; the organic phase was sepd., crystd. from diethyl ether-1,2-dichloroethane (4:1); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In water; 1,2-dichloro-ethane to soln. of crown ether in 1,2-dichloroethane added aq. mixt. of Na2PtCl4 and sodium dithiolate; mixt. stirred for 2 h at room temp.; filtered; ppt. dissolved in MeCN/CH3COCH3 (1:1); soln. slowly evapd.; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | In water; 1,2-dichloro-ethane to soln. of crown ether in 1,2-dichloroethane added aq. mixt. of Na2PtCl4 and sodium dithiolate; mixt. stirred for 2 h at room temp.; filtered; ppt. dissolved in MeCN/CH3COCH3 (1:1); soln. slowly evapd.; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In dichloromethane; water addn. of aq. soln. of zinc compd. and sodium thiocyanate to CH2Cl2 soln.of crown ether deriv., stirring for 2 h at room temp.; filtration, dissolving in CH3CN, slow evapn. for 1 wk, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | In dichloromethane; water addn. of aq. soln. of cadmium compd. and sodium thiocyanate to CH2Cl2 soln. of crown ether deriv., stirring for 2 h at room temp.; filtration, dissolving in CH3CN, slow evapn. for 1 wk, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | In dichloromethane; water addn. of aq. soln. of mercury compd. and sodium thiocyanate to CH2Cl2 soln. of crown ether deriv., stirring for 2 h at room temp.; filtration, dissolving in CH3CN, slow evapn. for 1 wk, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | Stage #1: 2,3-naphthalenediol With tetrabutylammomium bromide; sodium hydroxide In benzene at 60℃; for 0.5h; Stage #2: tetraethylene glycol di(p-toluenesulfonate) In benzene for 15h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: methanesulfonic acid; phosphorus pentoxide / 6 h / 20 °C 2.1: toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere 3.1: sodium hydroxide / water / 3 h / 50 °C 3.2: pH 2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: methanesulfonic acid; phosphorus pentoxide / 6 h / 20 °C 2: toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: methanesulfonic acid; phosphorus pentoxide / 6 h / 20 °C 2.1: toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere 3.1: sodium hydroxide / water / 3 h / 50 °C 3.2: pH 2 4.1: toluene-4-sulfonic acid / toluene / 70 - 80 °C | ||
Multi-step reaction with 4 steps 1.1: methanesulfonic acid; phosphorus pentoxide / 6 h / 20 °C 2.1: toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere 3.1: sodium hydroxide / water / 3 h / 50 °C 3.2: pH 2 4.1: titanium(IV) tetraethanolate / toluene / 6 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: methanesulfonic acid; phosphorus pentoxide / 6 h / 20 °C 2.1: toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere 3.1: sodium hydroxide / water / 3 h / 50 °C 3.2: pH 2 4.1: toluene-4-sulfonic acid / toluene / 70 - 80 °C 5.1: acetonitrile / 0.01 h / UV-irradiation | ||
Multi-step reaction with 5 steps 1.1: methanesulfonic acid; phosphorus pentoxide / 6 h / 20 °C 2.1: toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere 3.1: sodium hydroxide / water / 3 h / 50 °C 3.2: pH 2 4.1: titanium(IV) tetraethanolate / toluene / 6 h / 100 °C / Inert atmosphere 5.1: acetonitrile / 0.01 h / UV-irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: methanesulfonic acid; phosphorus pentoxide / 6 h / 20 °C 2.1: toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere 3.1: sodium hydroxide / water / 3 h / 50 °C 3.2: pH 2 4.1: toluene-4-sulfonic acid / toluene / 70 - 80 °C 5.1: barium(II) perchlorate / acetonitrile | ||
Multi-step reaction with 5 steps 1.1: methanesulfonic acid; phosphorus pentoxide / 6 h / 20 °C 2.1: toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere 3.1: sodium hydroxide / water / 3 h / 50 °C 3.2: pH 2 4.1: titanium(IV) tetraethanolate / toluene / 6 h / 100 °C / Inert atmosphere 5.1: barium(II) perchlorate / acetonitrile |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: methanesulfonic acid; phosphorus pentoxide / 6 h / 20 °C 2.1: toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere 3.1: sodium hydroxide / water / 3 h / 50 °C 3.2: pH 2 4.1: toluene-4-sulfonic acid / toluene / 70 - 80 °C 5.1: barium(II) perchlorate / acetonitrile | ||
Multi-step reaction with 5 steps 1.1: methanesulfonic acid; phosphorus pentoxide / 6 h / 20 °C 2.1: toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere 3.1: sodium hydroxide / water / 3 h / 50 °C 3.2: pH 2 4.1: titanium(IV) tetraethanolate / toluene / 6 h / 100 °C / Inert atmosphere 5.1: barium(II) perchlorate / acetonitrile |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With methanesulfonic acid; phosphorus pentoxide at 20℃; for 6h; | 4.2. 1-(2,3,5,6,8,9,11,12-Octahydronaphtho[2,3-b][1,4,7,10,13]pentaoxacyclopentadecine-16-yl)ethanone (10) A modification of the previously reported procedure23 was used. Commercially available Eaton's reagent (ca. 8 ml that corresponds to 6.28 mmol of phosphorus(V) oxide) and acetic acid (0.20 ml, 3.45 mmol) were mixed at room temperature. Then naphtho-15-crown-5 ether (1 g, 3.14 mmol) was added. The reaction mixture was stirred at room temperature for ca. 6 h and then poured into water. The suspension was extracted with dichloromethane and the combined organic phases were washed with water. Removal of the dried (MgSO4) solvent gave a dark brown oil, which upon repeated extractions with hot heptane, afforded the product as an off-white solid (1.02 g, 90%), mp 126-129 °C. 1H NMR (250 MHz, CDCl3): δ 2.69 (s, 3H, CH3), 3.78-3.76 (m, 8H, 5'-CH2, 6'-CH2, 8'-CH2, 9'-CH2), 3.96-4.06 (m, 4H, 3'-CH2, 11'-CH2), 4.22-4.32 (m, 4H, 2'-CH2, 12'-CH2), 7.11 (s, 1H, 19'-H), 7.20 (s, 1H, 14'-H), 7.70 (d, J=8.6 Hz, 1H, 18'-H), 7.89 (dd, J=8.6 and 1.5 Hz, 1H, 17'-H), 8.31 (s, 1H, 15'-H). 13C NMR (250 MHz, CDCl3): δ 26.67, 68.50, 68.60, 69.32, 69.39, 70.37, 70.40, 71.41, 107.40, 109.15, 122.79, 126.72, 128.41, 128.60, 132.27, 133.14, 149.95, 151.48, 198.16. Anal. Calcd for C20H24O6: C, 66.65; H, 6.71. Found: C, 66.37; H, 6.68. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: trichlorophosphate 2: tetra(n-butyl)ammonium hydroxide / ethanol / 3 h / Reflux 3: acetonitrile |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: trichlorophosphate 2: tetra(n-butyl)ammonium hydroxide / ethanol / 3 h / Reflux 3: acetonitrile |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: trichlorophosphate 2: tetra(n-butyl)ammonium hydroxide / ethanol / 3 h / Reflux 3: acetonitrile |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; lithium perchlorate In ethanol at 20℃; | Experimental General procedure: For preparing complexes, the relevant salts and rown-ether were dissolved in ethanol; the resulting solutions were mixed in an equimolar proportion. The reaction mixture was allowed to stand in air for 2-3 days. A precipitate was filtered off, washed with cool ethanol and freshly distilled diethyl ether. The thus-prepared compounds were white powders. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; lithium iodide In ethanol at 20℃; | Experimental General procedure: For preparing complexes, the relevant salts and rown-ether were dissolved in ethanol; the resulting solutions were mixed in an equimolar proportion. The reaction mixture was allowed to stand in air for 2-3 days. A precipitate was filtered off, washed with cool ethanol and freshly distilled diethyl ether. The thus-prepared compounds were white powders. |