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[ CAS No. 41727-58-6 ] {[proInfo.proName]}

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Product Details of [ 41727-58-6 ]

CAS No. :41727-58-6 MDL No. :MFCD04070684
Formula : C8H6Cl2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :LEEKELDJRCUBEM-UHFFFAOYSA-N
M.W : 205.04 Pubchem ID :883207
Synonyms :

Calculated chemistry of [ 41727-58-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.34
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.46 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.94
Log Po/w (XLOGP3) : 2.94
Log Po/w (WLOGP) : 2.81
Log Po/w (MLOGP) : 2.28
Log Po/w (SILICOS-IT) : 3.26
Consensus Log Po/w : 2.65

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.2
Solubility : 0.129 mg/ml ; 0.000629 mol/l
Class : Soluble
Log S (Ali) : -3.15
Solubility : 0.144 mg/ml ; 0.000701 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.71
Solubility : 0.0398 mg/ml ; 0.000194 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.36

Safety of [ 41727-58-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501 UN#:N/A
Hazard Statements:H302-H312-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 41727-58-6 ]

* 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 [ 41727-58-6 ]

[ 41727-58-6 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 123-11-5 ]
  • [ 41727-58-6 ]
YieldReaction ConditionsOperation in experiment
73% With sulfuryl dichloride for 72h; Heating;
65% With trichloroisocyanuric acid; brilliant green carbocation In acetonitrile at 20℃; for 20h; Irradiation; regioselective reaction;
40% Stage #1: 4-methoxy-benzaldehyde With 3-aminopropyltriethoxysilane In acetonitrile for 0.166667h; Stage #2: With N-chloro-succinimide In acetonitrile at 20℃;
With sulfuryl dichloride

  • 2
  • [ 41727-58-6 ]
  • [ 2181-42-2 ]
  • 2-(3,5-Dichloro-4-methoxy-phenyl)-oxirane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; dimethyl sulfoxide 1.) THF, 0 deg C, 5 min, 2.) a) 0 deg C, 15 min, b) 25 deg C, 2h; Multistep reaction;
  • 3
  • [ 41727-58-6 ]
  • [ 543-24-8 ]
  • 4-(4-methoxy-3,5-dichlorobenzylidene)-2-methyl-5-oxazolone [ No CAS ]
YieldReaction ConditionsOperation in experiment
18.3% With sodium acetate In acetic anhydride at 100℃; for 2h;
  • 4
  • [ 4892-23-3 ]
  • [ 41727-58-6 ]
YieldReaction ConditionsOperation in experiment
97% With 4 A molecular sieve; pyridinium chlorochromate In dichloromethane at 20℃; for 1h;
94% R.8.c c c Title Compound Following a similar procedure to that described in section c of reference example 7, but using 3,5-dichloro-4-methoxyphenylmethanol (obtained in the preceding section) instead of 3,4-(methylenedioxy)phenylmethanol, the title compound of the example was obtained as an oil (94% yield). 1H-NMR (300 MHz, CDCl3 δ TMS): 3.99 (s, 3H), 7.82 (s, 2H), 9.86 (s, 1H).
91% With pyridinium chlorochromate In dichloromethane at 20℃; for 4h;
39% With pyridinium chlorochromate In dichloromethane 16.4 (E)-4-[3-(1-Adamantyl)-4-hydroxphenyl]-3,5-dichlorocinnamic acid. Step 4: 3,5-Dichloro-4-methoxybenzaldehyde. To a suspension of 3.60 g (17.3 mmol) of 3,5-Dichloro-4-methoxybenzyl alcohol in 40 ml of CH2Cl2 at 0° C., 5.00 g (23.1 mmol) of pyridinium chlorochromate was added. The reaction mixture was stirred at room temperature for 3 hours at which time the reaction was complete. The mixture was filtered, washed with EtOAc, dried (MgSO4), filtered, and concentrated. Flash column chromatography (20% EtOAc/hexane) yielded a pale yellow solid (1.39 g, 39%): m.p. 44-46° C.: Rf 0.63 (20% EtOAc/hexane). 1H NMR (400 MHz, CDCl3) δ3.99 (s, 3, OCH3), 7.83 (s, 2, ArH), 9.87 ppm (s, 1, CHO).
With pyridinium chlorochromate
With oxalyl dichloride; dimethyl sulfoxide; triethylamine 1.) CH2Cl2, -70 deg C, 1.5 h, 2.) CH2Cl2, -70 deg C - RT, 3 h; Yield given. Multistep reaction;

  • 6
  • [ 7677-24-9 ]
  • [ 41727-58-6 ]
  • [ 20989-17-7 ]
  • (3,5-Dichloro-4-methoxy-phenyl)-((S)-2-hydroxy-1-phenyl-ethylamino)-acetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% In chloroform at 0℃;
  • 7
  • [ 41727-58-6 ]
  • [ 925-90-6 ]
  • [ 213470-64-5 ]
YieldReaction ConditionsOperation in experiment
85% In diethyl ether at 0℃; for 0.5h;
  • 8
  • [ 41727-58-6 ]
  • (2-chloro-5-methoxybenzyl)(triphenyl)phosphonium bromide [ No CAS ]
  • 1,3-Dichloro-5-[(E)-2-(2-chloro-5-methoxy-phenyl)-vinyl]-2-methoxy-benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In dichloromethane for 24h; Heating;
  • 9
  • [ 41727-58-6 ]
  • chromic acid [ No CAS ]
  • [ 37908-97-7 ]
  • 10
  • [ 7677-24-9 ]
  • [ 41727-58-6 ]
  • [ 20989-17-7 ]
  • [ 249757-10-6 ]
  • [(S)-(3,5-dichloro-4-methoxyphenyl)-(S)-(2-hydroxy-1-phenylethylamino)]acetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 64% 2: 26% Stage #1: 3,5-dichloro-4-methoxybenzaldehyde; (2S)-2-phenylglycinol In chloroform at 20℃; for 5h; Stage #2: trimethylsilyl cyanide In methanol; chloroform at 20℃; for 15h;
  • 11
  • [ 41727-58-6 ]
  • [ 1530-32-1 ]
  • (E)-2,6-dichloro-4-(1'-propenyl)anisole [ No CAS ]
  • [ 441284-62-4 ]
YieldReaction ConditionsOperation in experiment
32% With sodium hexamethyldisilazane In tetrahydrofuran; hexane; toluene at 20℃; for 12h;
  • 13
  • [ 4248-19-5 ]
  • [ 41727-58-6 ]
  • [ 873-55-2 ]
  • [benzenesulfonyl-(3,5-dichloro-4-methoxy-phenyl)-methyl]-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With formic acid In methanol; water at 20℃; for 72h;
  • 14
  • [ 41727-58-6 ]
  • (3,5-dichloro-4-methoxy-benzylidene)-carbamic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: formic acid / methanol; H2O / 72 h / 20 °C 2: 1.4 g / anhydrous potassium carbonate / tetrahydrofuran / 17 h / Heating
  • 15
  • [ 41727-58-6 ]
  • (R)-[1-(3,5-dichloro-4-methoxy-phenyl)-2-nitro-ethyl]-carbamic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: formic acid / methanol; H2O / 72 h / 20 °C 2: 1.4 g / anhydrous potassium carbonate / tetrahydrofuran / 17 h / Heating 3: ethyldiisopropylamine; anhydrous zinc triflate; (-)-(1R,2S)-N-methylephedrine / molecular sieves 4 Angstroem / -20 °C
  • 16
  • [ 41727-58-6 ]
  • (S)-[1-(3,5-dichloro-4-methoxy-phenyl)-2-nitro-ethyl]-carbamic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: formic acid / methanol; H2O / 72 h / 20 °C 2: 1.4 g / anhydrous potassium carbonate / tetrahydrofuran / 17 h / Heating 3: ethyldiisopropylamine; anhydrous zinc triflate; (-)-(1R,2S)-N-methylephedrine / molecular sieves 4 Angstroem / -20 °C
  • 17
  • [ 41727-58-6 ]
  • 5-(3,5-dichloro-4-methoxy-phenyl)-1-(4-methanesulfonyl-phenyl)-1<i>H</i>-imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene / Heating 2: K2CO3 / methanol; 1,2-dimethoxy-ethane / Heating
  • 18
  • [ 41727-58-6 ]
  • 4-chloro-5-(3,5-dichloro-4-methoxyphenyl)-1-(4-methylsulfonylphenyl)imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: toluene / Heating 2: K2CO3 / methanol; 1,2-dimethoxy-ethane / Heating 3: 75 percent / N-chlorosuccinimide / acetonitrile / 24 h / 81 °C
  • 19
  • [ 24295-27-0 ]
  • [ 41727-58-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 99 percent / LiAlH4 / diethyl ether / 1 h / 20 °C 2: 97 percent / PCC; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 20 °C
Multi-step reaction with 2 steps 1: 88 percent / LiAlH4 / tetrahydrofuran / 4 h / 20 °C 2: 91 percent / PCC / CH2Cl2 / 4 h / 20 °C
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / Heating 2: oxalyl dichloride; dimethyl sulfoxide; triethylamine / 1.) CH2Cl2, -70 deg C, 1.5 h, 2.) CH2Cl2, -70 deg C - RT, 3 h
  • 20
  • [ 41727-58-6 ]
  • (+/-)-(1R,2S)-1-(3',5'-dichloro-4'-methoxyphenyl)-1,2-propanediol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 32 percent / NaHMDS / hexane; toluene; tetrahydrofuran / 12 h / 20 °C 2: 53 percent / AD-mix(R); MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C
Multi-step reaction with 4 steps 1: 85 percent / diethyl ether / 0.5 h / 0 °C 2: 97 percent / PDC / CH2Cl2 / 25 °C 3: 1.) TMSCl, Et3N, NaI, 2.) OsO4, NMO / 1.) MeCN, 25 deg C, overnight, 2.) Me2CO, 2-methyl-2-propanol, 0 deg C, 2 h 4: 95 percent / Zn(BH4)2 / diethyl ether / 0.5 h / 0 °C
  • 21
  • [ 41727-58-6 ]
  • (1R,2S)-1-(3',5'-dichloro-4'-methoxyphenyl)-1,2-propanediol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 32 percent / NaHMDS / hexane; toluene; tetrahydrofuran / 12 h / 20 °C 2: 29 percent / AD-mix(R); MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C
  • 22
  • [ 41727-58-6 ]
  • [ 193073-55-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: CHCl3 / 5 h / 20 °C 1.2: 64 percent / CHCl3; methanol / 15 h / 20 °C 2.1: 10 percent / hydrochloric acid / 15 h / 20 °C
Multi-step reaction with 2 steps 1: 61 percent / CHCl3 / 0 °C 2: HCl
  • 23
  • [ 41727-58-6 ]
  • [ 213470-65-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 85 percent / diethyl ether / 0.5 h / 0 °C 2: 97 percent / PDC / CH2Cl2 / 25 °C
  • 24
  • [ 41727-58-6 ]
  • [ 213470-68-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 85 percent / diethyl ether / 0.5 h / 0 °C 2: 97 percent / PDC / CH2Cl2 / 25 °C 3: 1.) TMSCl, Et3N, NaI, 2.) OsO4, NMO / 1.) MeCN, 25 deg C, overnight, 2.) Me2CO, 2-methyl-2-propanol, 0 deg C, 2 h
  • 25
  • [ 41727-58-6 ]
  • 3,5-Dichloro-N-(4-methanesulfonyl-phenyl)-4-methoxy-benzamidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine; hydroxylamine hydrochloride / 1.) RT, 15 min, 2.) toluene, reflux, 4 h 2: trimethylaluminum / 1.) toluene, a) 0 deg C - RT, b) RT, 3.5 h, 2.) toluene, 70 deg C - 75 deg C, 17 h
  • 26
  • [ 41727-58-6 ]
  • 2-(3,5-dichloro-4-methoxyphenyl)-1-[4-(methylsulfonyl)phenyl]-4-trifluoromethyl-1H-imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: pyridine; hydroxylamine hydrochloride / 1.) RT, 15 min, 2.) toluene, reflux, 4 h 2: trimethylaluminum / 1.) toluene, a) 0 deg C - RT, b) RT, 3.5 h, 2.) toluene, 70 deg C - 75 deg C, 17 h 3: sodium hydrogencarbonate / isopropyl alcohol / 20 h / 75 - 80 °C 4: toluene-4-sulfonic acid / toluene / 72 h / Heating
  • 27
  • [ 41727-58-6 ]
  • [ 1027152-07-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine; hydroxylamine hydrochloride / 1.) RT, 15 min, 2.) toluene, reflux, 4 h 2: trimethylaluminum / 1.) toluene, a) 0 deg C - RT, b) RT, 3.5 h, 2.) toluene, 70 deg C - 75 deg C, 17 h 3: sodium hydrogencarbonate / isopropyl alcohol / 20 h / 75 - 80 °C
  • 28
  • [ 41727-58-6 ]
  • 3,5-dichloro-4-methoxyphenylpyruvic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 18.3 percent / sodium acetate / acetic anhydride / 2 h / 100 °C 2: 64.5 percent / HCl / acetic acid / 2 h / 140 - 160 °C
  • 29
  • [ 41727-58-6 ]
  • (3,5-Dichloro-4-methoxy-benzyl)-(2,2-dimethoxy-ethyl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 0.33 h / Heating 2: sodium borohydride / ethanol / 24 h / Ambient temperature
  • 30
  • [ 41727-58-6 ]
  • [ 95333-57-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 0.33 h / Heating 2: sodium borohydride / ethanol / 24 h / Ambient temperature 3: 12 N HCl / ethanol; H2O / 2 h / Heating 4: BBr3 / CH2Cl2 / 1.5 h
  • 31
  • [ 41727-58-6 ]
  • [ 105764-05-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 0.33 h / Heating 2: sodium borohydride / ethanol / 24 h / Ambient temperature 3: 12 N HCl / ethanol; H2O / 2 h / Heating
  • 32
  • [ 41727-58-6 ]
  • [ 80751-56-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) 50percent NaH suspension in mineral oil, Me2SO / 1.) THF, 0 deg C, 5 min, 2.) a) 0 deg C, 15 min, b) 25 deg C, 2h 2: 18 h / 110 °C
  • 33
  • [ 41727-58-6 ]
  • [ 46338-99-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 2: LiAlH4 / tetrahydrofuran / Heating
  • 34
  • [ 41727-58-6 ]
  • 4-[4-Chloro-5-(3,5-dichloro-4-methoxyphenyl)imidazol-1-yl]benzenesulfonamide Hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
15 4-[4-Chloro-5-(3,5-dichloro-4-methoxyphenyl)imidazol-1-yl]benzenesulfonamide Hydrochloride EXAMPLE 15 4-[4-Chloro-5-(3,5-dichloro-4-methoxyphenyl)imidazol-1-yl]benzenesulfonamide Hydrochloride Following a similar procedure to that described in example 11, but using 3,5-dichloro-4-methoxybenzaldehyde (obtained in reference example 8) instead of 4-fluoro-3-methoxybenzaldehyde, and in the last step carrying out the extraction from the aqueous phase after acidification with hydrochloric acid, the title compound of the example was obtained as a white solid. 1H-NMR (300 MHz, CDCl3+CD3OD δ TMS): 3.92 (s, 3H), 7.31 (s, 2H), 7.49 (d, J=8.4 Hz, 2H), 8.0 (m, 3H).
  • 35
  • [ 41727-58-6 ]
  • [ 540779-07-5 ]
YieldReaction ConditionsOperation in experiment
91% With potassium carbonate In tetrahydrofuran 16.5 (E)-4-[3-(1-Adamantyl)-4-hydroxphenyl]-3,5-dichlorocinnamic acid. Step 5: Ethyl (E)-3,5-dichloro-4-methoxycinnamate. To a suspension of 1.39 g (6.78 mmol) of 3,5-dichloro-4-methoxybenzaldehyde and 4.56 g (32.9 mmol) of K2CO3 in 50 ml of anhydrous THF under Ar, 5.0 ml (25.2 mmol) of triethyl phosphonoacetate was added. The reaction mixture was stirred at room temperature for 4 days at which time the reaction was complete. The mixture was extracted with EtOAc, washed with brine and water, dried (MgSO4), filtered, and concentrated. Flash column chromatography (10% EtOAc/hexane) yielded a white solid (1.70 g, 91%): m.p. 85-87° C.: Rf 0.73 (20% EtOAc/hexane); 1H NMR (400 MHz, CDCl3) δ1.34 (t, J=7.2 Hz, 3, CH3), 3.93 (s, 3, OCH3), 4.26 (q, J=7.2 Hz, 2, CH2), 6.3 d, J=16.0 Hz, 1, HC=CCO), 7.46 (s, 2, ArH), 7.50 ppm (d, J=16.0 Hz, 1, C=CHCO).
  • 36
  • [ 41727-58-6 ]
  • [ 1345017-05-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid / ethanol / 2 h / Reflux 2: potassium carbonate / ethanol / 5 h / Reflux
  • 37
  • [ 41727-58-6 ]
  • [ 1345017-11-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetic acid / ethanol / 2 h / Reflux 2: potassium carbonate / ethanol / 5 h / Reflux 3: hydrogenchloride / 1,4-dioxane; dichloromethane / 0.08 h
  • 38
  • [ 41727-58-6 ]
  • [ 74-89-5 ]
  • C9H9Cl2NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In ethanol for 2h; Reflux; 1-Methyl-4-(3-fluoro-4-methoxyphenyl)-5-(3,5-dichloro-4-methoxyphenyl)-imidazole x HCl (6f) A mixture of 3,5-dichloro-4-methoxybenzaldehyde (72 mg, 0.35 mmol) and 33% MeNH2/ethanol (220 μL, 1.78 mmol) in ethanol (15 mL) was treated with AcOH (125 μL, 2.19 mmol) and refluxed for 2 h. After cooling to room temperature, 5 (110 mg, 0.35 mmol)nand K2CO3 (500 mg, 3.62 mmol) were added and the reaction mixture was refluxed for 5 h. The solvent was evaporated, the residue was diluted with ethyl acetate, washed with water, dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by column chromatography (silica gel 60, ethyl acetate/methanol 95:5, Rf = 0.64) giving the imidazole as a colorless oil. This oil was dissolved in CH2Cl2 (5 mL) and treated with 3 M HCl in dioxane (1 mL). After stirring for 5 min the solvent was evaporated and the residue was crystallized from CH2Cl2/hexane. Yield: 100 mg (69%); colorless solid of mp 190 °C; νmax (ATR)/cm-1 3375, 3163, 3015, 2940, 2841, 2726, 1626, 1592, 1581, 1524, 1497, 1466, 1443, 1424, 1396, 1307, 1281, 1252, 1207, 1183, 1135, 1101, 1021, 990, 879, 866, 809, 765, 727; 1H NMR (300 MHz, DMSO-d6) δ 3.66 (3 H, s), 3.84 (3 H, s), 3.92 (3 H, s), 7.0-7.1 (1 H, m), 7.23 (1 H, t, JHF = 17.6 Hz), 7.36 (1 H, dd, J = 12.6 Hz, 2.2 Hz), 7.72 (2 H, s), 9.27 (1 H, s); 13C NMR (75.5 MHz, DMSO-d6) δ 34.0, 56.1, 60.9, 114.4, 114.6, 114.8, 115.1, 119.7, 124.0, 124.1, 124.2, 126.5, 129.2, 129.6, 131.8, 136.0, 147.7, 147.9, 149.5, 152.7, 153.1; m/z (EI) 382 (71) [M+, free base], 380 (100) [M+], 367 (32), 365 (50).
  • 39
  • [ 2314-36-5 ]
  • [ 74-88-4 ]
  • [ 41727-58-6 ]
YieldReaction ConditionsOperation in experiment
24% Preparation of 4-(3,5-dichloro-4-methoxybenzyl)-7-ethoxyisoquinolin-8-ol hydrochloride 693,5-Dichloro-4-methoxybenzaldehvde RBO 40104In a 100 ml_ round bottom flask, <strong>[2314-36-5]3,5-dichloro-4-hydroxybenzaldehyde</strong> (1 .0 g, 5.23 mmol) was dissolved in acetone (50 ml_) and K2CO3 (1 .01 g, 7.32 mmol) was added at RT. The mixture was stirred at RT for 30 min, then Mel (1 .34 g, 9.41 mmol) was added and reaction was stirred at reflux for another 5 h and finally at RT overnight. Acetone was evaporated and the residue was taken back in EtOAc (200 ml_) and water (200 ml_). The aqueous layer was further extracted with EtOAc (3x100 ml_). The combined organic layers were washed with brine (100 ml_), dried over Na2SO4, filtered and concentrated to dryness to give 3,5-dichloro-4-methoxybenzaldehyde RBO 40104 (257 mg, 24percent yield) as an off-white solid.RBO 40104MW: 205.04; Yield: 24percent; Off-white solid.1H-NMR (CDCIs, delta): 3.99 (s, 3H, OMe), 7.83 (s, 2H, 2xArH), 9.87 (s, 1 H, CHO).MS-ESI m/z (percent rel. Int.): 205.0/207.0 ([MH]+, 100/65).HPLC: Method A, XBridge.(TM). column, detection UV 254 nm, RT = 5.68 min, peak area 99.0percent.
  • 40
  • [ 41727-58-6 ]
  • [ 1351592-04-5 ]
  • [ 1351593-58-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3,5-dichloro-4-methoxybenzaldehyde; 2-((2,2-diethoxyethylamino)methyl)-6-ethoxyphenol With hydrogenchloride In ethanol; water at 90℃; for 0.166667h; Stage #2: With sodium hydrogencarbonate In water 4-(3,5-Dichloro-4-methoxybenzyl)-7-ethoxyisoquinolin-8-ol hydrochloride 69In an ace pressure tube, 2-((2,2-diethoxyethylamino)methyl)-6-ethoxyphenol SAO 33014 (355 mg, 1 .25 mmol) and 3,5-dichloro-4-methoxybenzaldehyde RBO 40104 (257 mg, 1 .25 mmol) were dissolved in EtOH:37% HCI solution = 1 :1 (10 ml_). The reaction mixture was stirred at 90°C for 10 min, and then cooled to RT. The volatiles were removed under vacuum and the residue was taken back in EtOAc (200 ml_) and neutralized with a 10% NaHCO3 aqueous solution (20 ml_). The separated organic layer was washed with water (3x30 ml_), brine (30 ml_), dried over Na2SO4, filtered and evaporated to give a yellow solid. This solid was purified by column chromatography (S1O2, eluent dichloromethane:EtOAc = 100:0 to 50:50) to give, after evaporation and drying, 4-(3,5-dichloro-4-methoxybenzyl)-7-ethoxyisoquinolin-8-ol (89 mg). This solid was dissolved in MeOH (2 ml_) and a 0.49 HCI solution in MeOH (480 μΙ_, 0.24 mmol) was slowly added. The reaction mixture was stirred at 4°C for 15 min. After evaporation and drying under P2O5, 4-(3,5-dichloro-4-methoxybenzyl)-7- ethoxyisoquinolin-8-ol hydrochloride (58 mg, 1 1 % yield) 69 was obtained as a yellow solid. MW: 414.72; Yield: 1 1 %; Yellow Solid; Mp (°C): 216.4Rf. 0.35 (CH2CI2:EtOAc = 50:50, free base).1H-NMR (CDsOD, δ): 1 .49 (t, 3H, J = 6 Hz, CH3), 3.83 (s, 3H, OMe), 4.32 (q, 2H, J = 6 Hz OCH2), 4.49 (s, 2H, CH2), 7.33 (s, 2H, 2xArH), 7.76 (d, 1 H, J = 12 Hz, ArH), 8.01 (d, 1 H, J = 12 Hz, ArH), 8.18 (s, 1 H, ArH), 9.68 (s, 1 H, ArH).13C-NMR (CD3OD, δ): 13.7, 34.2, 59.9, 65.6, 1 15.1 , 1 19.2, 125.5, 127.4, 129.1 , 129.4, 131 .1 , 135.1 , 136.2, 141 .8, 145.3, 145.8, 151 .2.MS-ESI m/z (% rel . Int.): 378.0/380.0 ([MH]+, 100/65).HPLC: Method A, XBridge column, detection UV 254 nm, RT = 4.76 min, peak area 99.0%.
  • 42
  • [ 41727-58-6 ]
  • (+)-4-(3,5-dichloro-4-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-cinnamyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ammonium acetate / isopropyl alcohol / 80 °C 2: Daicel Chiralcel OD / Resolution of racemate 3: methanol; sodium hydroxide / 2 h
  • 44
  • [ 41727-58-6 ]
  • (+)-4-(3,5-dichloro-4-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-cinnamyl ester 5-(2-cyanoethyl) ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ammonium acetate / isopropyl alcohol / 80 °C 2: Daicel Chiralcel OD / Resolution of racemate
  • 45
  • [ 41727-58-6 ]
  • [ 1379515-62-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: piperidine / benzene / Reflux 2: ammonium acetate / isopropyl alcohol / 80 °C 3: methanol; sodium hydroxide
  • 46
  • [ 41727-58-6 ]
  • [ 14451-18-4 ]
  • propynoic acid cinnamyl ester [ No CAS ]
  • [ 1395226-36-4 ]
YieldReaction ConditionsOperation in experiment
12.2% With ammonium acetate In isopropyl alcohol at 80℃; Step 1. Synthesis of racemic 4-(3,5-dichloro-4-methoxy-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-cinnamyl ester 5-(2-cyanoethyl) ester (10f) 3,5-dichloro-4-methoxy-benzaldehyde (5; 318 mg, 1.86 mmol), propynoic acid 2-cyanoethyl ester (7; 229 mg, 1.86 mmol), propynoic acid cinnamyl ester (9; 351 mg, 1.88 mmol), and ammonium acetate (270 mg, 3.50 mmol) were dissolved in 2-propanol and stirred overnight at 80 °C. The solvent was evaporated under reduced pressure, and the residue was extracted three times with EtOAc from water. The title compound (116 mg, 0.23 mmol, 12.2%) was obtained after purification by silica gel chromatography (hexane/EtOAc, 3:1). 1H NMR (CDCl3): 2.56 (2H, t), 3.83 (3H, s), 3.83 (3H, s), 4.18-4.40 (2H, m), 4.63-4.83 (2H, m), 4.87 (1H, s), 6.23 (1H, dt), 6.34 (1H, br d), 6.58 (1H, d), and 7.23-7.47 (9H, m). MS (ESI, m/z) 511 (M-H)-.
  • 47
  • [ 41727-58-6 ]
  • [ 1569438-41-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triphenylphosphine; zinc / dichloromethane / 48 h / -5 - 20 °C / Inert atmosphere; Schlenk technique 2.1: tert.-butyl lithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 2.2: -60 - 20 °C / Inert atmosphere 3.1: potassium carbonate / N,N-dimethyl-formamide / 0.25 h / Schlenk technique; Inert atmosphere; Darkness 3.2: 4 h / 65 °C / Schlenk technique; Inert atmosphere; Darkness
  • 48
  • [ 41727-58-6 ]
  • [ 1569438-42-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triphenylphosphine; zinc / dichloromethane / 48 h / -5 - 20 °C / Inert atmosphere; Schlenk technique 2.1: tert.-butyl lithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 2.2: -60 - 20 °C / Inert atmosphere 3.1: potassium carbonate / N,N-dimethyl-formamide / 0.25 h / Schlenk technique; Inert atmosphere; Darkness 3.2: 4 h / 65 °C / Schlenk technique; Inert atmosphere; Darkness
  • 49
  • [ 558-13-4 ]
  • [ 41727-58-6 ]
  • [ 1569438-62-5 ]
YieldReaction ConditionsOperation in experiment
83% With triphenylphosphine; zinc In dichloromethane at -5 - 20℃; for 48h; Inert atmosphere; Schlenk technique;
  • 50
  • [ 3612-18-8 ]
  • [ 41727-58-6 ]
  • (E)-1-ethyl-3,5-bis(3,5-dichloro-4-methoxybenzylidene)-4-piperidone hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% Stage #1: N-ethyl-4-piperidone; 3,5-dichloro-4-methoxybenzaldehyde With sodium hydroxide In methanol; water at 20℃; for 1h; Stage #2: With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 0.0833333h;
  • 51
  • [ 90-15-3 ]
  • [ 41727-58-6 ]
  • [ 109-77-3 ]
  • 2-amino-4-(3,5-dichloro-4-methoxyphenyl)-4H-benzo[h]chromene-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% Stage #1: 3,5-dichloro-4-methoxybenzaldehyde; malononitrile With triethylamine In acetonitrile at 20℃; for 0.5h; Stage #2: α-naphthol In acetonitrile at 20℃; for 1h; 2-Amino-4-(3,5-dichloro-4-methoxyphenyl)-4H-benzo[h]chromene-3-carbonitrile (2d) 3,5-Dichloro-4-methoxybenzaldehyde (205 mg, 1.0 mmol) and malononitrile (70 mg, 1.0 mmol) were dissolved in MeCN (5 mL) and three drops of Et3N were added. The reaction mixture was stirred at room temperature for 30 min. 1-Naphthol (144 mg, 1.0 mmol) was added and the reaction mixture was stirred at room temperature for 1 h. The formed precipitate was collected, washed with MeCN and n-hexane and dried in vacuum. Yield: 197 mg (0.50 mmol, 50%); colorless solid of m.p. 243 °C;
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