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Chemical Structure| 726-18-1 Chemical Structure| 726-18-1

Structure of 726-18-1

Chemical Structure| 726-18-1

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Product Details of [ 726-18-1 ]

CAS No. :726-18-1
Formula : C15H16O2
M.W : 228.29
SMILES Code : COC1=CC=C(CC2=CC=C(OC)C=C2)C=C1
MDL No. :MFCD00048046
InChI Key :WECJUPODCKXNQK-UHFFFAOYSA-N
Pubchem ID :219137

Safety of [ 726-18-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 726-18-1 ]

* 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 [ 726-18-1 ]

[ 726-18-1 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 104-21-2 ]
  • [ 5720-07-0 ]
  • [ 726-18-1 ]
  • 2
  • [ 64-19-7 ]
  • [ 105-13-5 ]
  • [ 5405-95-8 ]
  • [ 104-21-2 ]
  • [ 726-18-1 ]
  • 3
  • [ 104-21-2 ]
  • [ 726-18-1 ]
  • [ 53039-57-9 ]
  • [ 1293915-27-1 ]
  • [ 1293915-33-9 ]
  • [ 1293915-31-7 ]
  • [ 1293915-37-3 ]
  • 4-(2-methoxy-5-methylbenzyl)-2-(4-methoxybenzyl)-1-methoxybenzene [ No CAS ]
  • 4
  • [ 104-21-2 ]
  • [ 100-66-3 ]
  • [ 726-18-1 ]
YieldReaction ConditionsOperation in experiment
95% With proton-exchanged montmorillonite; at 20℃; General procedure: To a mixture of 12 (66 mg, 0.366 mmol) and arenes or heteroarenes(1 mL) was added H-mont (260 mg). The reaction mixturewas stirred at room temperature until the TLC indicated the consumptionof the starting material. The mixture was filtered toremove H-mont, and the filtrate was evaporated under reducedpressure. The residue was purified by flash chromatography (petroleumether/ethyl acetate 200:1 to 10:1) to give the product.Following the procedure, 14ceg were prepared.
95% With proton-exchanged montmorillonite; at 20℃; General procedure: To a mixture of anisole (3 mL) and an acetate (0.366 mmol) wasadded H-mont (260 mg). The reaction mixture was stirred at thetemperature indicated in Table 5 until the TLC indicated the consumptionof the acetate. The mixture was filtered to remove Hmont,and the filtrate was evaporated under reduced pressure. Theresidue was purified by flash chromatography (petroleum ether/ethyl acetate 300:1 to 10:1) to give the product. The results aresummarized in Table 5.
85% With trifluorormethanesulfonic acid; at 20℃; for 0.333333h;Neat (no solvent); General procedure: 430 muL of anisyl acetate (2.5 mmol, 1 equiv) and 2.2 mL of anisole (12.25 mmol, 5 equiv) were placed into a 10 mL round-bottom flask equipped with a magnetic stir-bar. Then 11 muL 5% of pure triflic acid (0.125 mmol) was added and the solution was stirred for 20 min. The crude was analyzed by 1H NMR and GC-MS. Purification by column chromatography gave 484 mg (85% yield) of bis(4-methoxyphenyl)methane, which was identical to an authentic sample.
  • 5
  • isofraxetin 6-O-β-D-glucopyranoside [ No CAS ]
  • [ 487-89-8 ]
  • [ 50656-75-2 ]
  • [ 55396-45-7 ]
  • [ 486-21-5 ]
  • [ 726-18-1 ]
  • [ 30567-87-4 ]
  • [ 22248-13-1 ]
  • [ 6935-99-5 ]
  • [ 20913-18-2 ]
  • 8'-dehydroxymethyl cleomiscosin A [ No CAS ]
  • [ 103-81-1 ]
  • [ 61281-37-6 ]
  • [ 66-22-8 ]
  • (+)-isoschizandrin [ No CAS ]
  • 6-methoxy-5′′-demethoxydaphneticin [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.9 mg; 1.3 mg; 1.1 mg; 0.8 mg; 5.9 mg; 2.0 mg; 1.0 mg; 2.1 mg; 2.3 mg; 1.1 mg; 1.1 mg; 0.9 mg; 1.1 mg; 1.2 mg; 1.7 mg With Angelica sinensis (Oliv.) Diels callus; In methanol; for 168.0h; General procedure: Isofraxetin-6-O-beta-D-glucopyranoside (859 mg) was dissolved in CH3OH (86.0 mL) and distributed into 59 bottles of the suspension cultures of A. sinensis callus equally. The mixture was co-cultured for 7 days, then the cells and medium were separated by filtration. The medium was concentrated to 200 mL and partitioned by the same volume of EtOAc (ethylacetate) and n-BuOH (n-butyl alcohol) successively for three times. Next, the organic phase was collected and concentrated under the reduced pressure toyield EtOAc extract (Fr. 1, 0.25 g) and n-BuOH extract (Fr. 2, 1.20 g) respectively. The cells were dried under 50C, and then were extracted in an ultrasonic bath with CH3OH for 30 min. After that, the extract was further partitioned by EtOAc and n-BuOH respectively to afford EtOAc extract (Fr. 3,0.62 g) and n-BuOH extract (Fr. 4, 1.46 g). Compared with the experimental group, cultures and medium without isofraxetin-6-O-b-D-glucopyranoside act as control group and was processed to get Fr. 5-8 by the same procedures. The combination of Fr. 1 and Fr. 3 (EE, 0.87 g) was subjected on ODS column chromatography (CC) with gradient elution CH3OH/H2O (from 0:100 to 100:0) to get five subfractions (Fr. 1a-5a). Next, Fr. 1a was separated by HPLC with ODS column (250 mm 10 mm, flow rate 3 mL/min) eluted with CH3OH/H2O(49: 51) to afford compounds 5 (2.1 mg, tR = 14 min), 6 (2.3 mg, tR = 18 min)and 3 (5.9 mg, tR = 39 min). Fr. 2a was firstly fractioned by silica gel CC(3 50 cm) with gradient elution petroleum/acetone (0:100-100:0) to get substraction 2a-1 and 2a-2. Then Fr. 2a-1 was purified by HPLC with ODS column (250 mm 10 mm, flow rate 3 mL/min) with CH3CN/H2O (37: 63) to provide compounds 8 (1.0 mg, tR = 22 min), 10 (1.1 mg, tR = 27 min) and 14(1.2 mg, tR = 35 min). While compound 15 (0.9 mg, tR = 25 min) was purifiedfrom substration Fr. 2a-2, using HPLC with ODS column (250 mm 10 mm,flow rate 3 mL/min) eluted with CH3CN/H2O (39: 61). And Fr. 3a was chromatographied on HPLC with ODS column (250 mm 10 mm, flow rate3 mL/min) to yield compounds 9 (1.1 mg, tR = 40 min) and 11 (0.9 mg,tR = 56 min) using CH3OH/H2O (35: 65) as elute. However, compounds 12(0.8 mg, tR = 37 min) and 13 (1.3 mg, tR = 49 min) were obtained from Fr. 4a byHPLC with ODS column (250 mm 10 mm, flow rate 3 mL/min) using CH3CN/H2O (8:92) as eluting solvent. Equally, Fr. 2 and Fr. 4 was combined as BE(2.66 g) to subject on ODS CC with CH3OH/H2O (from 0:100 to 100:0) to getseven fractions (Fr. 1b-7b). Fr. 1b was isolated using HPLC with ODS column(250 mm 10 mm, flow rate 3 mL/min) eluted by CH3OH/H2O (20: 80) andthen purified by Sephadex LH-20 chromatography eluted with CH3OH to afford compounds 1 (1.1 mg) and 2 (1.7 mg). Furthermore, compound 4 (2.0 mg) wasobtained from Fr. 3b by recrystallization in CH3OH. Next, Fr. 4b was subjectedon silica gel CC (3 50 cm) with gradient elution CH2Cl2/CH3OH (0:100-100:0)to get substraction Fr. 4b-1 and Fr. 4b-2. Then Fr. 4b-1 was purified by HPLCwith ODS column (250 mm 10 mm, flow rate 3 mL/min) with CH3CN/H2O(13: 87) to provide compounds 7 (1.1 mg, tR = 19 min) and 16 (1.8 mg,tR = 39 min).
 

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