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[ CAS No. 14174-08-4 ] {[proInfo.proName]}

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Chemical Structure| 14174-08-4
Chemical Structure| 14174-08-4
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Product Details of [ 14174-08-4 ]

CAS No. :14174-08-4 MDL No. :MFCD00059934
Formula : C12H16O4 Boiling Point : -
Linear Structure Formula :- InChI Key :OAJNZFCPJVBYHB-UHFFFAOYSA-N
M.W : 224.25 Pubchem ID :586075
Synonyms :

Safety of [ 14174-08-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 14174-08-4 ]

* 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.

  • Downstream synthetic route of [ 14174-08-4 ]

[ 14174-08-4 ] Synthesis Path-Downstream   1~96

  • 1
  • [ 50-00-0 ]
  • [ 14174-08-4 ]
  • [ 134767-38-7 ]
  • 3
  • [ 14174-08-4 ]
  • (4aR,14aS)-Dodecahydro-5,8,11,14-tetraoxa-benzocyclododecene [ No CAS ]
  • 5
  • [ 14174-08-4 ]
  • [ 78554-67-3 ]
YieldReaction ConditionsOperation in experiment
75% With nitric acid; acetic acid; In chloroform; at 20℃; for 24h;Cooling with ice; In a 100 mL round bottom flask, add the <strong>[14174-08-4]benzo-12-crown-4</strong> (2 mmol) prepared in step (2),10 mL of chloroform and 6 mL of acetic acid were slowly added to 4 mL of 68 wt% concentrated nitric acid under ice bath conditions, and after stirring at room temperature for 24 h,The reaction solution was neutralized with alkali, and the chloroform layer was separated. After the aqueous layer was extracted with chloroform, the combined chloroform layer was dried over anhydrous magnesium sulfate.The chloroform was distilled off under reduced pressure to obtain a yellow crude product, which was separated by column chromatography.Elution with (V ethyl acetate: V petroleum ether = 1: 2), compound III (4-nitro<strong>[14174-08-4]benzo-12-crown-4</strong>) was obtained with a yield of 75%;
59% With nitric acid; In acetonitrile;Reflux; To a refluxing solution of 6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzo- cyclododecene (6.50 g, 28.98 mmol) in 65 mL of acetonitrile, was added nitric acid (56%, 5.4 mL) dropwise. When TLC showed the completion of reaction, 160 mL of water was added. The resulting solution was kept at 2 C overnight. The precipitate was collected and washed until to neutral pH, giving desired 2-Nitro-6,7,9,10,12,13-hexahydro-5,8,l l,14- tetraoxa-benzocyclododecene as yellow solid (4.61 g, 59% yield).
With nitric acid; In water; acetonitrile; at 85℃; for 0.5h; A solution of compound 31-2 (50 mg, 222.96 mmol, 1 eq) in acetonitrile (2 mL) was warmed up to 85C.Concentrated nitric acid (38 mg, 337.71 mmol, 27.14 mL, 56% purity, 1.51 eq) was slowly added dropwisely. After thecompletion of the dropwise addition, the mixture was stirred at 85C for 0.5 hour. The reaction mixture was cooled toroom temperature and poured into ice (about 10 mL) to quench the reaction. The mixture was extracted with ethyl acetate(3x10 mL). The above organic phases were combined, dried over anhydrous sodium sulfate and filtered. The filtratewas concentrated under reduced pressure to give compound 31-3, which was directly used in the next step without theneed for any further purification. 1H NMR (400 MHz, CDCl3) δppm 7.86-7.89 (m, 1 H), 7.81 (d, J=2.8 Hz, 1H), 6.93 (d,J=8.8Hz, 1H), 4.17-4.23 (m, 4H), 3.84-3.85 (m, 2H), 3.77-3.80 (m, 2H), 3.71 (s, 4H).
  • 8
  • [ 14174-08-4 ]
  • [ 108-24-7 ]
  • [ 107996-83-8 ]
  • 9
  • [ 120-80-9 ]
  • [ 112-26-5 ]
  • [ 14174-08-4 ]
YieldReaction ConditionsOperation in experiment
14.4% With lithium hydroxide monohydrate; In water; butan-1-ol; at 95℃;Inert atmosphere; Under nitrogen, to the mixture of (22.02 g, 199.98 mmol) in 220 mL of n- butanol, was added 46 mL of aqueous solution of LiOH H2O (18.46 g, 439.94 mmol). The mixture was heated to 95 C, followed by addition of l-chloro-2-[2-(2-chloro-ethoxy)-ethoxy] -ethane (37.43 g, 200.09 mmol) in 240 mL of n-butanol. The reaction was heated overnight, then filtrated. 1 M of aqueous hydrochloric acid was added to adjust pH to 8. After removal of most n-butanol under reduced pressure, the residue was extracted with dichloromethane 250 mL x 2. The combined organic layer was washed with brine and dried over anhydrous MgSCH. The crude product was purified by column chromatography on silica gel, giving 6.5 g of 6,7,9,10,12,13-Hexahydro- 5,8,11,14-tetraoxa-benzocyclododecene as yellow oil, 14.4% yield.
  • 11
  • [ 120-80-9 ]
  • [ 19249-03-7 ]
  • [ 14174-08-4 ]
YieldReaction ConditionsOperation in experiment
52% In a 100 ml flask, dissolve catechol (5 mmol) and 2.5 mmol of tetrabutylammonium bromide (TBAB) in 30 mL of a toluene solution, and then add a 50 wt% aqueous NaOH solution (10 mL).Stir the mixture at 50-60 C for 30 minutes, and then add (30 mL) containing triethylene glycol di-p-toluenesulfonate (5 mmol, also known as triethylene glycol bis (p-toluenesulfonate)) Of toluene solution.The resulting mixture was stirred vigorously at this temperature under reflux for 16 h.After the reaction,The organic layer was separated with H 2 O (3 × 200 mL), washed with saturated brine, and dried over MgSO 4.The solvent was removed in vacuo and the residue was extracted with ethyl acetate (3 × 50 mL).After cooling, the product was separated by column chromatography and eluted with (V ethyl acetate: V petroleum ether = 2: 1) to obtain compound II (benzo-12-crown-4) with a yield of 52%;
28% Mix 2.2kg (20mol) catechol, 12.4kg (89.6mol) potassium carbonate and 300L DMF, stir for about 30min., heat up to 85-90C, add prepared 1,8-bis(p-toluenesulfonate)-3,6-dioxoctane(2) by dropping 40L of 9.17kg (20mol) DMF solution, drip in 1.5-2h, drip and react for 30min., TLC check the reaction is completed (developing solvent: petroleum ether: ethyl acetate=1:1, Rf=0.58) . Aspirate about 40L of the reaction liquid, continue to repeat the above operation 3 to 5 times, filter with suction, evaporate DMF under reduced pressure, dissolve the residue with 240L of ethyl acetate, filter with suction, and distill under reduced pressure, and use petroleum ether: ethyl acetate = 1:1 for column chromatography. The solvent was recovered under reduced pressure, and the solid was recrystallized with isopropanol 1:2.5 (W/V) to obtain 1.376 kg of off-white powder with a yield of 28%.
  • 13
  • [ 14174-08-4 ]
  • [ 64-19-7 ]
  • [ 107996-83-8 ]
  • 2,3-(4,5-diacetyl)benzo-12-crown-4 ether [ No CAS ]
  • 14
  • [ 14174-08-4 ]
  • [ 802294-64-0 ]
  • 1-(6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-propan-1-one [ No CAS ]
  • 1-(3-Propionyl-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-propan-1-one [ No CAS ]
  • 15
  • [ 87494-76-6 ]
  • [ 14174-08-4 ]
  • 17
  • [ 14174-08-4 ]
  • [ 107-92-6 ]
  • 1-(6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-butan-1-one [ No CAS ]
  • 1-(3-Butyryl-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-butan-1-one [ No CAS ]
  • 18
  • [ 14174-08-4 ]
  • [ 109-52-4 ]
  • 1-(6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-pentan-1-one [ No CAS ]
  • 1-(3-Pentanoyl-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-pentan-1-one [ No CAS ]
  • 19
  • [ 14174-08-4 ]
  • [ 768-95-6 ]
  • 2-Adamantan-1-yl-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecene [ No CAS ]
  • 21
  • [ 1120-99-6 ]
  • [ 14174-08-4 ]
  • 5-(6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-2,5-dihydro-[1,2,4]triazin-3-ylamine [ No CAS ]
  • 22
  • [ 14174-08-4 ]
  • [ 54673-30-2 ]
  • [ 407-25-0 ]
  • 4-(5-Oxo-1-trifluoroacetyl-3-phenyl-1,2,5,6-tetrahydro-1,2,4-triazin-6-yl)benzo-12-crown-4 [ No CAS ]
  • 23
  • [ 14174-08-4 ]
  • [ 78554-67-3 ]
  • 4',5'-dinitro-B12C4 [ No CAS ]
  • 24
  • [ 14174-08-4 ]
  • 1-acetyl-3-phenyl-1,6-dihydro-4<i>H</i>-[1,2,4]triazin-5-one [ No CAS ]
  • 3-(1-acetyl-5-oxo-3-phenyl-1,4,5,6-tetrahyro-1,2,4-triazin-6-yl)benzo-12-crown-4 [ No CAS ]
  • 25
  • [ 14174-08-4 ]
  • 1-acetyl-3-<i>p</i>-tolyl-1,6-dihydro-4<i>H</i>-[1,2,4]triazin-5-one [ No CAS ]
  • [ 420118-24-7 ]
  • 26
  • [ 14174-08-4 ]
  • [ 89179-74-8 ]
  • [ 407-25-0 ]
  • 3-Ethylsulfanyl-6-(6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-1-(2,2,2-trifluoro-acetyl)-1,6-dihydro-4H-[1,2,4]triazin-5-one [ No CAS ]
  • 27
  • [ 14174-08-4 ]
  • [ 54673-30-2 ]
  • [ 407-25-0 ]
  • 6-(6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-3-phenyl-1-(2,2,2-trifluoro-acetyl)-1,6-dihydro-4H-[1,2,4]triazin-5-one [ No CAS ]
  • 28
  • [ 14174-08-4 ]
  • [ 36993-93-8 ]
  • [ 407-25-0 ]
  • [ 420118-14-5 ]
  • 29
  • [ 14174-08-4 ]
  • 3-(4-Chlorophenyl)-2H-1,2,4-triazin-5-one [ No CAS ]
  • [ 407-25-0 ]
  • 3-(4-Chloro-phenyl)-6-(6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-1-(2,2,2-trifluoro-acetyl)-1,6-dihydro-4H-[1,2,4]triazin-5-one [ No CAS ]
  • 30
  • [ 10234-40-9 ]
  • [ 6315-52-2 ]
  • [ 14174-08-4 ]
  • 31
  • [ 54535-06-7 ]
  • [ 107-21-1 ]
  • [ 14174-08-4 ]
  • 32
  • [ 99700-26-2 ]
  • [ 14174-08-4 ]
  • 33
  • [ 14174-08-4 ]
  • [ 2032-35-1 ]
  • C26H33BrO8 [ No CAS ]
  • 34
  • [ 50-00-0 ]
  • [ 14174-08-4 ]
  • [ 906096-99-9 ]
  • 36
  • [ 14174-08-4 ]
  • C56H56O10 [ No CAS ]
  • 38
  • [ 120-80-9 ]
  • [ 14174-08-4 ]
  • 39
  • [ 111875-70-8 ]
  • [ 14174-08-4 ]
  • 40
  • [ 14174-08-4 ]
  • N-(2,3,5,6,8,9-hexahydro-1,4,7,10-benzotetraoxacyclododecin-12-yl)-4-(1-pyrenyl)butyramide [ No CAS ]
  • 41
  • [ 14174-08-4 ]
  • 3-(5-oxo-phenylamino-2,5-dihydro-1,2,4-triazin-6-yl)benzo-12-crown-4 [ No CAS ]
  • 42
  • [ 14174-08-4 ]
  • 6-(6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-3-<i>p</i>-tolyl-2<i>H</i>-[1,2,4]triazin-5-one [ No CAS ]
  • 43
  • [ 14174-08-4 ]
  • [ 420118-28-1 ]
  • 44
  • [ 14174-08-4 ]
  • 4-(3-Amino-1,2,4-triazin-5-yl)benzo-12-crown-4 [ No CAS ]
  • 45
  • [ 14174-08-4 ]
  • [ 264142-13-4 ]
  • 46
  • [ 14174-08-4 ]
  • bis(2-nitro-4,5-(1,4,7,10-tetraoxadecamethylene)phenyl) disulfide [ No CAS ]
  • 47
  • [ 14174-08-4 ]
  • bis(2-nitro-4,5-(1,4,7,10-tetraoxadecamethylene)phenyl) diselenide [ No CAS ]
  • 48
  • [ 14174-08-4 ]
  • [ 167300-08-5 ]
  • 49
  • [ 14174-08-4 ]
  • (1S,5R,7S)-3-(6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-2,4-dioxo-1,5,7-tripropyl-3-aza-bicyclo[3.3.1]nonane-7-carbonyl chloride [ No CAS ]
  • 50
  • [ 14174-08-4 ]
  • (1S,5R,7S)-3-(6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-2,4-dioxo-1,5,7-tripropyl-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid methyl ester [ No CAS ]
  • 51
  • [ 14174-08-4 ]
  • (1R,5S,7R)-3-(6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-2,4-dioxo-1,5,7-tripropyl-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid (6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-amide [ No CAS ]
  • 52
  • [ 14174-08-4 ]
  • (1R,5S,7R)-3-(6,7,9,10,12,13,15,16-Octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecen-2-yl)-2,4-dioxo-1,5,7-tripropyl-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid (6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-amide [ No CAS ]
  • 53
  • [ 14174-08-4 ]
  • (1R,5S,7R)-3-(6,7,9,10,12,13,15,16,18,19-Decahydro-5,8,11,14,17,20-hexaoxa-benzocyclooctadecen-2-yl)-2,4-dioxo-1,5,7-tripropyl-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid (6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-amide [ No CAS ]
  • 54
  • [ 14174-08-4 ]
  • [ 120434-45-9 ]
  • 55
  • [ 14174-08-4 ]
  • 4'-picrylamino benzo-12-crown-4 [ No CAS ]
  • 56
  • [ 14174-08-4 ]
  • [ 109789-52-8 ]
  • 57
  • [ 14174-08-4 ]
  • [ 109789-47-1 ]
  • 58
  • [ 31255-10-4 ]
  • [ 14174-08-4 ]
  • 60
  • tantalum(V) oxide [ No CAS ]
  • [ 14174-08-4 ]
  • [ 7664-39-3 ]
  • [ 7732-18-5 ]
  • [(benzo-12-crown-4)2*H3O][TaF6] [ No CAS ]
  • 61
  • [ 14174-08-4 ]
  • [ 7783-71-3 ]
  • [ 7664-39-3 ]
  • [ 7732-18-5 ]
  • [(benzo-12-crown-4)2*H3O][TaF6] [ No CAS ]
  • 63
  • [ 10544-50-0 ]
  • [ 14174-08-4 ]
  • sodium amalgam [ No CAS ]
  • (K[Mo(13)C(N(CH3(C(2)H3)2C)(C6H3(CH3)2))3])2 [ No CAS ]
  • Na(1+)*2(C4H4(C2O)(C2H4O)3)*[Mo(13)CS(N(CH3(C(2)H3)2C)(C6H3(CH3)2))3](1-)=[Na(C24H32O8)][Mo(13)CS(N(C4H3(2)H6)(C8H9))3] [ No CAS ]
  • 64
  • [ 14174-08-4 ]
  • [ 121669-21-4 ]
  • C24H32LiO8(1+)*ClO4(1-) [ No CAS ]
  • 66
  • [ 1121-60-4 ]
  • [ 14174-08-4 ]
  • [ 1366625-26-4 ]
YieldReaction ConditionsOperation in experiment
49% With trifluorormethanesulfonic acid; In chloroform; at 25℃; General procedure: The carbonyl substrate (0.1 g) is dissolved in 1-2 mL of anhydrous CHCl3 and 2.0 equiv of a benzocrown ether is added to the solution. To this mixture, CF3SO3H (8.0 equiv; H2SO4 may be used in some cases) is added dropwise with stirring. The reaction is stirred at room temperature for at least 2 h, after which, the mixture is poured over several grams of ice. The resulting solution is extracted three times with CHCl3. The organic phase is subsequently washed three times with water and dried over MgSO4 solution. Removal of the solvent provides the product.
  • 67
  • [ 14174-08-4 ]
  • [ 611-09-6 ]
  • [ 1366625-22-0 ]
YieldReaction ConditionsOperation in experiment
95% With trifluorormethanesulfonic acid; In chloroform; at 25℃; General procedure: The carbonyl substrate (0.1 g) is dissolved in 1-2 mL of anhydrous CHCl3 and 2.0 equiv of a benzocrown ether is added to the solution. To this mixture, CF3SO3H (8.0 equiv; H2SO4 may be used in some cases) is added dropwise with stirring. The reaction is stirred at room temperature for at least 2 h, after which, the mixture is poured over several grams of ice. The resulting solution is extracted three times with CHCl3. The organic phase is subsequently washed three times with water and dried over MgSO4 solution. Removal of the solvent provides the product.
  • 68
  • [ 14174-08-4 ]
  • [ 485-47-2 ]
  • [ 1366625-24-2 ]
YieldReaction ConditionsOperation in experiment
77% With sulfuric acid; In chloroform; at 25℃; General procedure: The carbonyl substrate (0.1 g) is dissolved in 1-2 mL of anhydrous CHCl3 and 2.0 equiv of a benzocrown ether is added to the solution. To this mixture, CF3SO3H (8.0 equiv; H2SO4 may be used in some cases) is added dropwise with stirring. The reaction is stirred at room temperature for at least 2 h, after which, the mixture is poured over several grams of ice. The resulting solution is extracted three times with CHCl3. The organic phase is subsequently washed three times with water and dried over MgSO4 solution. Removal of the solvent provides the product.
  • 69
  • [ 14174-08-4 ]
  • [ 111380-75-7 ]
  • [ 1380508-63-3 ]
YieldReaction ConditionsOperation in experiment
75% With polyphosphoric acid; at 80 - 85℃; for 0.5h; General procedure: 4.2.1. Method A. molecular clip 2 was obtained in 50% yield as described6b Method B. A mixture of bisether 8 (1 g, 2.65 mmol) and corresponding benzocrown ether (5.42 mmol) in PPA (30 g) was stirred vigorously at 80-85 for 30 min. A deep purple color was formed in 5 min. To the cooled reaction mixture was added water (150 mL) and product was extracted with CHCl3 (3×50 mL). The organic layer was washed with water until neutral (∼3×50 mL) and subjected to azeotropic drying. The solvent was removed at reduced pressure and the residue was dissolved in a mixture of CHCl3/MeOH (50:1, 100 mL) and filtered through SiO2 (~30 mL). The solvent was removed at reduced pressure and the crude product was purified as described below. Method C. The procedure is similar to Method B, with exception that tetraol 9 (1.1 g, 2.65 mmol) was used instead bisether 8. Method D. A suspension of NaH (0.288 g, 12 mmol) in DMSO (26 mL) was heated with stirring at 70 for 30 min. The resulting mixture was cooled to room temperature and a solution of 11 (0.78 g, 2.65 mmol) in DMSO (40 mL) was added. Stirring was continued for 20 min and then solution of 10 (5.92 g, 5.83 mmol) in DMSO (40 mL) was added dropwise over 5 min and the resulting mixture was stirred at room temperature for 24 h. The mixture was poured into ice water (400 mL) and acidified with HCl to pH~2. The resulting solid was filtered off, washed with water (3×50 mL). The crude product was purified as described below.
  • 70
  • [ 14174-08-4 ]
  • [ 101241-22-9 ]
  • [ 1380508-63-3 ]
YieldReaction ConditionsOperation in experiment
36% With polyphosphoric acid; at 80 - 85℃; for 0.5h; General procedure: 4.2.1. Method A. molecular clip 2 was obtained in 50% yield as described6b Method B. A mixture of bisether 8 (1 g, 2.65 mmol) and corresponding benzocrown ether (5.42 mmol) in PPA (30 g) was stirred vigorously at 80-85 for 30 min. A deep purple color was formed in 5 min. To the cooled reaction mixture was added water (150 mL) and product was extracted with CHCl3 (3×50 mL). The organic layer was washed with water until neutral (∼3×50 mL) and subjected to azeotropic drying. The solvent was removed at reduced pressure and the residue was dissolved in a mixture of CHCl3/MeOH (50:1, 100 mL) and filtered through SiO2 (~30 mL). The solvent was removed at reduced pressure and the crude product was purified as described below. Method C. The procedure is similar to Method B, with exception that tetraol 9 (1.1 g, 2.65 mmol) was used instead bisether 8. Method D. A suspension of NaH (0.288 g, 12 mmol) in DMSO (26 mL) was heated with stirring at 70 for 30 min. The resulting mixture was cooled to room temperature and a solution of 11 (0.78 g, 2.65 mmol) in DMSO (40 mL) was added. Stirring was continued for 20 min and then solution of 10 (5.92 g, 5.83 mmol) in DMSO (40 mL) was added dropwise over 5 min and the resulting mixture was stirred at room temperature for 24 h. The mixture was poured into ice water (400 mL) and acidified with HCl to pH~2. The resulting solid was filtered off, washed with water (3×50 mL). The crude product was purified as described below.
  • 71
  • [ 55400-73-2 ]
  • [ 120-80-9 ]
  • [ 14174-08-4 ]
  • 72
  • [ 14174-08-4 ]
  • C26H30O10 [ No CAS ]
  • 73
  • [ 14174-08-4 ]
  • C36H42O12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75.6% With iron(III) chloride; dipotassium peroxodisulfate; at 10 - 15℃; for 2h; 500 ml of propylene carbonate was added into 1000 ml four-necked flask, potassium peroxodisulfate 116.2g (0.43mmol) and <strong>[14174-08-4]benzo-12-crown-4</strong> ether 96.4g (0.43mmol) were added, stirred, and cooled at internal temperature of 10 degrees C. Anhydrous iron(III) chloride 276.3g (1.68mmol) was added little by little, reacted with the internal temperature of 10-15 degrees C for 2 hours. 2000 ml of water was added after completion of reaction, cooled, and stirred for 10 minutes. The aqueous layer of the solution was separated, and the organic layer was washed with 200 ml of 1N hydrochloric acid aqueous solution. The aqueous layer was removed and the organic layer was washed with 500 ml of salt solution. 600 ml of methanol was added to the organic layer, and crystallized for 1 hour at an internal temperature of 15-25 degrees C. The crystals were dried and obtained 72.2 g (75.6% of yield) as thin purple crystal. It checked that the product was synthesized with the mass spectrum and the NMR spectrum.
  • 74
  • [ 14174-08-4 ]
  • 1-[3-[[5-fluoro-2-(2,5,8,11-tetraoxabicyclo[10.4.0]hexadeca-1(12),13,15-trien-14-ylamino)pyrimidin-4-yl]amino]-1-piperidyl]prop-2-en-1-one [ No CAS ]
  • 75
  • [ 14174-08-4 ]
  • 12-(pyren-1-ylethynyl)-2,3,5,6,8,9-hexahydrobenzo[b][1,4,7,10]tetraoxacyclododecin [ No CAS ]
  • 76
  • [ 14174-08-4 ]
  • C30H24O4*Li(1+) [ No CAS ]
  • 77
  • [ 14174-08-4 ]
  • C30H24O4*Na(1+) [ No CAS ]
  • 78
  • [ 14174-08-4 ]
  • C30H24O4*K(1+) [ No CAS ]
  • 79
  • [ 14174-08-4 ]
  • C30H24O4*Mg(2+) [ No CAS ]
  • 80
  • [ 14174-08-4 ]
  • C30H24O4*Ba(2+) [ No CAS ]
  • 81
  • [ 14174-08-4 ]
  • C30H24O4*Rb(1+) [ No CAS ]
  • 82
  • [ 14174-08-4 ]
  • C30H24O4*Cs(1+) [ No CAS ]
  • 83
  • [ 14174-08-4 ]
  • 12-iodo-2,3,5,6,8,9-hexahydrobenzo[b][1,4,7,10]tetraoxacyclododecin [ No CAS ]
  • 84
  • [ 14174-08-4 ]
  • [ 68555-67-9 ]
  • C20H15F17O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With barium sulfate; acetic anhydride; acetic acid; In acetonitrile; at 85℃; for 12h; 1.68 g (7.5 mmol) of crown ether compound A1, 11.4 g (22.5 mmol) of compound B2, 17.4 g (42 mmol) of barium sulfate tetrahydrate, 45 mL of acetonitrile, 9 mL of acetic acid, 9 mL of acetic anhydride were added to the reaction flask. , reaction at 85 C for 12 h. After cooling to room temperature, it was filtered, and water was added and washed with diethyl ether. The organic layer was dried and purified with acetone petroleum ether(1:4) column chromatography.2.11 g of product C2 were obtained in 44% yield.
  • 85
  • [ 14174-08-4 ]
  • [ 102061-83-6 ]
  • [ 123405-62-9 ]
YieldReaction ConditionsOperation in experiment
51% With barium sulfate; acetic anhydride; acetic acid; In acetonitrile; at 85℃; for 15h; 2.24 g (10 mmol) of crown ether compound A1, 12.2 g (30 mmol) of compound B1, 23.2 g (56 mmol) of barium sulfate tetrahydrate, 60 mL of acetonitrile, 12 mL of acetic acid, 12 mL of acetic anhydride were added to the reaction flask.The reaction was carried out at 85 C for 15 h.After cooling to room temperature, it was filtered, and water was added and washed with diethyl ether. The organic layer was dried and purified with acetone petroleum ether (1:4) column chromatography.2.81 g of product C1 were obtained in a 51% yield.
  • 86
  • [ 14174-08-4 ]
  • [ 4224-70-8 ]
  • bromohexanoylbenzo-12-crown-4-ether [ No CAS ]
YieldReaction ConditionsOperation in experiment
With PPA; at 60 - 75℃; for 10h; In a 250 mL three-necked flask, add PPA (100 g), oil bath, and mechanically stir at 60 C for 10 min. Then add benzo 12-crown-4 ether (0.68 g, 3 mmol),6-Bromohexanoic acid (0.58 g, 3 mmol) was heated to 75 C and reacted for 10 h.After the reaction is completed, add ice water, slowly add distilled water (100-200 mL) and keep stirring until the PPA is completely dissolved.Extract the aqueous layer 3-5 times with chloroform (30 mL) as the extractant. Combine the extracts.Wash with a saturated sodium carbonate solution to remove 6-bromohexanoic acid, and then wash with a saturated sodium chloride solution to remove the inorganic salt in the organic layer.Anhydrous sodium sulfate was added to the extract to dry it, followed by vacuum filtration, and chloroform was recovered by rotary evaporation to obtain bromohexanoyl 12-crown-4 ether.
  • 87
  • [ 14174-08-4 ]
  • 1-hexanoylbenzo-12-crown-4-ether-3-methylimidazolium bistrifluoromethanesulfonylimide [ No CAS ]
  • 88
  • [ 14174-08-4 ]
  • 1-hexanoylbenzo-12-crown-4-ether-3-methylimidazolium bromide [ No CAS ]
  • 89
  • [ 14174-08-4 ]
  • Na[Re(η5-Cp)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate)] [ No CAS ]
  • [Na(benzo-12-crown-4)2][Re(η5-Cp)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate)] [ No CAS ]
  • 90
  • [ 75-77-4 ]
  • [ 14174-08-4 ]
  • Na[Re(η5-Cp)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate)] [ No CAS ]
  • [ 4039-32-1 ]
  • Re(H)(η5-C5H4SiMe3)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate) [ No CAS ]
  • 91
  • [ 14174-08-4 ]
  • [ 2769-71-3 ]
  • Na[Re(η5-Cp)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate)] [ No CAS ]
  • [(benzo-12-crown-4)2Na][(XylNC)Re(η5-Cp)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate)] [ No CAS ]
  • 92
  • [ 14174-08-4 ]
  • [ 60-29-7 ]
  • [(Et2O)Na(OC)Re(η5-Cp)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate)]2 [ No CAS ]
  • [(benzo-12-crown-4)2Na]{Na[(OC)Re(η5-Cp)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate)]2} [ No CAS ]
  • 93
  • [ 14174-08-4 ]
  • C31H27N5O4 [ No CAS ]
  • 94
  • [ 14174-08-4 ]
  • C31H32ClN5O5S [ No CAS ]
  • 95
  • [ 14174-08-4 ]
  • [ 79-04-9 ]
  • C14H17ClO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With aluminum (III) chloride; In dichloromethane; at 0 - 20℃; for 2h; Under ice cooling (0C), dissolve 3,4-<strong>[14174-08-4]benzo-12-crown-4</strong>-benzene (18g, 80.3mmol) in 200mL of dry CH2Cl2, add chloroacetyl chloride (9.1g, 80.3mmol), Then, AlCl3 (16.1g, 120.5mmol) was slowly added in portions, and after all AlCl3 was added, it was naturally raised to room temperature and stirring continued for 2h. TLC (petroleum ether: ethyl acetate = 1:1, Rf = 0.52) detected the disappearance of the raw material point, the reaction solution was poured into ice water hydrochloric acid to decompose, the organic layer was separated, the aqueous layer was extracted 3 times with CH2Cl2, and the organic layers were combined. It was washed with water to neutrality, dried with anhydrous Na2SO4, filtered and concentrated to obtain 22.6 g of crude light yellow solid. , Suction filtration, and ethanol recrystallization to obtain 19.2 g of slightly yellow to yellow crystalline powder with a yield of 79%.
  • 96
  • [ 14174-08-4 ]
  • 2-acetamido-2-[2-(3,4-benzo-12-crown-4)-2-oxoethyl]-1,3-malonic acid diethyl ester [ No CAS ]
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