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Product Details of [ 40181-00-8 ]

CAS No. :40181-00-8 MDL No. :MFCD11935403
Formula : C11H14O3 Boiling Point : -
Linear Structure Formula :- InChI Key :SGUITGYYSSRXRY-UHFFFAOYSA-N
M.W : 194.23 Pubchem ID :20514626
Synonyms :

Safety of [ 40181-00-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 UN#:
Hazard Statements:H302-H312-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 40181-00-8 ]

* 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 [ 40181-00-8 ]

[ 40181-00-8 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 30405-75-5 ]
  • [ 40181-00-8 ]
YieldReaction ConditionsOperation in experiment
With iodine; mercury(II) oxide Einw.von pulverisiertem KOH auf die aether.Loesung des gebildeten Jodhydrins und Destillation des Reaktionsproduktes unter normalem Druck;
(i) 4-nitroperoxybenzoic acid, (ii) BF3-Et2O; Multistep reaction;
Multi-step reaction with 2 steps 1: tert.-butylhydroperoxide; selenium(IV) oxide / chlorobenzene; acetic acid; dichloromethane / 24 h / 20 °C 2: carbon tetrabromide; triphenylphosphine / dichloromethane / 4 h / 20 °C
  • 3
  • [ 40181-00-8 ]
  • [ 40181-01-9 ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride In diethyl ether
  • 4
  • [ 51698-53-4 ]
  • [ 40181-00-8 ]
YieldReaction ConditionsOperation in experiment
95% With diisobutylaluminium hydride In toluene at 0℃; for 1.5h;
  • 5
  • [ 5460-32-2 ]
  • [ 107-18-6 ]
  • [ 40181-00-8 ]
  • [ 61871-67-8 ]
  • 6
  • [ 40181-00-8 ]
  • 3-benzyl-7,8-dimethoxy-5-methyl-1,3-dihydrobenzo[d]azepin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: benzene / 24 h / Heating 2: pyridine / CH2Cl2 / 2 h / 25 °C 3: 92 percent / sodium periodate / methanol; H2O / 4 h / 25 °C 4: 76 percent / p-TsOH / benzene / 0.33 h / Heating 5: 90 percent / Raney nickel / tetrahydrofuran; ethanol / 0.5 h / 25 °C
  • 7
  • [ 40181-00-8 ]
  • [ 499993-06-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: benzene / 24 h / Heating 2: pyridine / CH2Cl2 / 2 h / 25 °C 3: 92 percent / sodium periodate / methanol; H2O / 4 h / 25 °C 4: 76 percent / p-TsOH / benzene / 0.33 h / Heating
  • 8
  • [ 40181-00-8 ]
  • [ 499993-28-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene / 24 h / Heating 2: pyridine / CH2Cl2 / 2 h / 25 °C
  • 9
  • [ 40181-00-8 ]
  • [ 499993-27-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene / 24 h / Heating 2: pyridine / CH2Cl2 / 2 h / 25 °C
  • 10
  • [ 40181-00-8 ]
  • 1-benzyl-5-(3,4-dimethoxyphenyl)-3-ethylsulfanyl-4-methyl-1,5-dihydropyrrol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: benzene / 24 h / Heating 2: pyridine / CH2Cl2 / 2 h / 25 °C 3: 74 percent / sodium periodate / methanol; H2O / 2 h / 25 °C 4: 62 percent / p-TsOH / benzene / 0.33 h / Heating
  • 11
  • [ 40181-00-8 ]
  • [ 499993-04-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: benzene / 24 h / Heating 2: pyridine / CH2Cl2 / 2 h / 25 °C 3: 92 percent / sodium periodate / methanol; H2O / 4 h / 25 °C
  • 12
  • [ 40181-00-8 ]
  • [ 499993-03-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: benzene / 24 h / Heating 2: pyridine / CH2Cl2 / 2 h / 25 °C 3: 74 percent / sodium periodate / methanol; H2O / 2 h / 25 °C
  • 13
  • [ 40181-00-8 ]
  • [ 40181-02-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether 2: Py
  • 14
  • [ 40181-00-8 ]
  • [ 1386351-16-1 ]
  • [ 1386351-20-7 ]
YieldReaction ConditionsOperation in experiment
With sodium tetrahydroborate optical yield given as %ee;
  • 15
  • [ 93-16-3 ]
  • [ 1192280-90-2 ]
  • [ 40181-00-8 ]
  • 16
  • [ 6380-23-0 ]
  • [ 201230-82-2 ]
  • [ 40181-00-8 ]
  • [ 61871-67-8 ]
YieldReaction ConditionsOperation in experiment
90% With chloro(1,5-cyclooctadiene)rhodium(I) dimer; hydrogen; sodium 4-dodecylbenzenesulfonate; Sodium; 2-[bis-(2-diphenylphosphanyl-ethyl)-carbamoyl]-benzenesulfonate In water; toluene at 60℃;
80% With dicarbonylacetylacetonato rhodium (I); hydrogen; triphenylphosphine In methanol; toluene at 65℃; for 0.966667h; regioselective reaction;
80% With (acetylacetonato)dicarbonylrhodium (l); hydrogen; triphenylphosphine In methanol; toluene at 70℃; for 0.833333h; regioselective reaction;
With methoxy(cyclooctadiene)rhodium(I) dimer; tris(2,4-di-tert-butylphenyl)phosphite; hydrogen In toluene at 60℃; for 4h; Schlenk technique; Glovebox;

  • 17
  • [ 1131-62-0 ]
  • [ 40181-00-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C 1.2: 24 h / 20 °C 2.1: tert.-butylhydroperoxide; selenium(IV) oxide / chlorobenzene; acetic acid; dichloromethane / 24 h / 20 °C 3.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 4 h / 20 °C
Multi-step reaction with 2 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 1.2: 16 h / 0 - 20 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; tetrahydrofuran / 1 h / 70 °C / Inert atmosphere 1.2: 20 h / 20 °C 2.1: zinc(II) chloride / toluene / 1 h / 110 °C
Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / 0 °C 1.2: 0 - 20 °C 2.1: perchloric acid / diethyl ether; water / 0.17 h / 0 °C

  • 18
  • [ 1424343-23-6 ]
  • [ 40181-00-8 ]
YieldReaction ConditionsOperation in experiment
83% With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 4h;
  • 19
  • [ 40181-00-8 ]
  • [ 1386351-30-9 ]
  • [ 1386351-96-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6-bromo-5-methoxy-2,2-dimethyl-2H-chromene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333h; Stage #2: 2-(3,4-di-methoxyphenyl)propionaldehyde In tetrahydrofuran; hexane at -78 - 20℃; for 0.5h;
Stage #1: 6-bromo-5-methoxy-2,2-dimethyl-2H-chromene With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333h; Stage #2: 2-(3,4-di-methoxyphenyl)propionaldehyde In tetrahydrofuran at -78℃; for 0.5h; 29 Example 29 n-BuLi (1.4 equivalent) was added to anhydrous THF solution containing the compound 51 (1.5 equivalent) prepared in Manufacturing Example 27 drop by drop at -78°C, which was stirred at -78°C to generate aryl anions. The mixture was stirred at-78°C for 20 minutes, to which the compound 55 (1.0 equivalent) prepared in Manufacturing Example 14 was added, followed by stirring for 30 minutes with raising the reaction temperature to room temperature. The reaction mixture was treated with saturated NH4Cl aqueous solution, followed by extraction with EtOAc. The extract was washed with brine and then dried over MgSO4. The residue obtained after evaporating the solvent was purified by flash column chromatography (EtOAc:n-hexane=1:2) to give the secondary alcohol.
Stage #1: 6-bromo-5-methoxy-2,2-dimethyl-2H-chromene With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333h; Stage #2: 2-(3,4-di-methoxyphenyl)propionaldehyde In tetrahydrofuran at -78 - 20℃; for 0.5h; 29 n-BuLi (1.4 equivalent) was added to anhydrous THF solution containing the compound 51 (1.5 equivalent) prepared in Manufacturing Example 27 drop by drop at -78° C., which was stirred at -78° C. to generate aryl anions. The mixture was stirred at -78° C. for 20 minutes, to which the compound 55 (1.0 equivalent) prepared in Manufacturing Example 14 was added, followed by stirring for 30 minutes with raising the reaction temperature to room temperature. The reaction mixture was treated with saturated NH4Cl aqueous solution, followed by extraction with EtOAc. The extract was washed with brine and then dried over MgSO4. The residue obtained after evaporating the solvent was purified by flash column chromatography (EtOAc:n-hexane=1:2) to give the secondary alcohol.
  • 20
  • [ 40181-00-8 ]
  • [ 1386351-30-9 ]
  • [ 1386350-30-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C 1.2: 0.5 h / -78 - 20 °C 2.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 °C 1.2: 0.5 h / -78 °C 2.1: Dess-Martin periodane / dichloromethane / 1 h
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 °C 1.2: 0.5 h / -78 - 20 °C 2.1: Dess-Martin periodane / dichloromethane / 1 h
  • 21
  • [ 15964-79-1 ]
  • [ 40181-00-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 1.2: 1 h / -78 °C 2.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / -78 °C
Multi-step reaction with 2 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / -78 °C
Multi-step reaction with 3 steps 1.1: diisobutylaluminium hydride / tetrahydrofuran; diethyl ether / 1 h / -78 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 1 h 3.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / -78 °C
Multi-step reaction with 3 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 1.2: 1 h / -78 °C 2.1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 °C 3.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 0.5 h / -78 °C 3.2: 1 h / -30 - 0 °C

  • 22
  • [ 93-40-3 ]
  • [ 40181-00-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C 1.2: 0.17 h 2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 2.2: 1 h / -78 °C 3.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / -78 °C
Multi-step reaction with 3 steps 1.1: oxalic acid / dichloromethane; N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C 1.2: 0.17 h 2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 1 h / -78 °C / Inert atmosphere 3.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / -78 °C
Multi-step reaction with 4 steps 1.1: oxalyl dichloride / dichloromethane / 0.5 h / 0 - 20 °C 1.2: 0.17 h 2.1: diisobutylaluminium hydride / tetrahydrofuran; diethyl ether / 1 h / -78 °C 3.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 3.2: 1 h 4.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / -78 °C
  • 23
  • [ 29207-02-1 ]
  • [ 40181-00-8 ]
YieldReaction ConditionsOperation in experiment
61% With diisobutylaluminium hydride In tetrahydrofuran at -78℃; for 1h;
61% With diisobutylaluminium hydride In tetrahydrofuran at -78℃; for 1h; 14 Manufacturing Example 14: Anhydrous THF solution containing the 2-(3,4-dimethoxyphenyl)propanoate obtained above was stirred, during which DIBAL-H (16.0 mL, 1 M in THF solution) was added drop by drop with maintaining the temperature at -78°C. The mixture was stirred again for 1 hour at the same temperature. Rochelle aqueous solution was carefully added thereto for 15 minutes. The mixture of the two phases was stirred vigorously at 0 °C for 1 hour, which was added to water. The water layer was extracted with EtOAc (*2) and the organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. Then, the obtained residue was purified by flash column chromatography (EtOAc:n-hexane=1:2) to give the compound 55 of Manufacturing Example 14 (yield: 61%, 1.58 g). 1H NMR (CDCl3, 300 MHz) δ 9.63 (d, 1H, J = 1.5 Hz), 6.86 (d, 1H, J = 8.2 Hz), 6.74 (m, 1H), 6.66 (d, 1H, J = 2.0 Hz), 3.85 (s. 6H), 3.56 (q, 1H, J = 6.9 Hz), 1.40 (d, 3H, J = 6.9 Hz).
Multi-step reaction with 2 steps 1.1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 °C 2.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 0.5 h / -78 °C 2.2: 1 h / -30 - 0 °C
  • 24
  • [ 5703-21-9 ]
  • [ 40181-00-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 1 h 2.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / -78 °C
  • 25
  • 2-(3,4-dimethoxyphenyl)propanoate [ No CAS ]
  • [ 40181-00-8 ]
YieldReaction ConditionsOperation in experiment
61% With diisobutylaluminium hydride In tetrahydrofuran at -78℃; for 1h; 14 Manufacturing Example 14 Preparation of 2-(3,4-Dimethoxyphenyl)propanal (55) Anhydrous THF solution containing the 2-(3,4-dimethoxyphenyl)propanoate obtained above was stirred, during which DIBAL-H (16.0 mL, 1 M in THF solution) was added drop by drop with maintaining the temperature at -78° C. The mixture was stirred again for 1 hour at the same temperature. Rochelle aqueous solution was carefully added thereto for 15 minutes. The mixture of the two phases was stirred vigorously at 0° C. for 1 hour, which was added to water. The water layer was extracted with EtOAc (×2) and the organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. Then, the obtained residue was purified by flash column chromatography (EtOAc:n-hexane=1:2) to give the compound 55 of Manufacturing Example 14 (yield: 61%, 1.58 g). [0220] 1H NMR (CDCl3, 300 MHz) δ 9.63 (d, 1H, J=1.5 Hz), 6.86 (d, 1H, J=8.2 Hz), 6.74 (m, 1H), 6.66 (d, 1H, J=2.0 Hz), 3.85 (s. 6H), 3.56 (q, 1H, J=6.9 Hz), 1.40 (d, 3H, J=6.9 Hz)
  • 26
  • [ 40181-00-8 ]
  • (2R,3R)-ethyl 3-(3,4-dimethoxyphenyl)-2-hydroxy-3-methyl-4-oxobutanoate [ No CAS ]
  • (2S,3S)-ethyl 3-(3,4-dimethoxyphenyl)-2-hydroxy-3-methyl-4-oxobutanoate [ No CAS ]
  • (2R,3S)-ethyl 3-(3,4-dimethoxyphenyl)-2-hydroxy-3-methyl-4-oxobutanoate [ No CAS ]
  • (2S,3R)-ethyl 3-(3,4-dimethoxyphenyl)-2-hydroxy-3-methyl-4-oxobutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 88 % ee 2: 54 % ee With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea In tetrahydrofuran; toluene at 24℃; for 15h; Inert atmosphere; Overall yield = 74 %; stereoselective reaction;
  • 27
  • [ 40181-00-8 ]
  • [ 109-73-9 ]
  • [ 768-60-5 ]
  • N-butyl-4-(3,4-dimethoxyphenyl)-1-(4-methoxyphenyl)pent-1-yn-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With copper(I) bromide In toluene at 100℃; for 1h; Microwave irradiation; Inert atmosphere;
  • 28
  • [ 40181-00-8 ]
  • C35H49N3O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(I) bromide / toluene / 1 h / 100 °C / Microwave irradiation; Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 - 20 °C / Inert atmosphere
  • 29
  • 1,2-dimethoxy-4-(1-methoxyprop-1-en-2-yl)benzene [ No CAS ]
  • [ 40181-00-8 ]
YieldReaction ConditionsOperation in experiment
61% With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;
With perchloric acid In diethyl ether; water at 0℃; for 0.166667h;
  • 30
  • 2-(3,4-dimethoxy-phenyl)-2-methyl-oxirane [ No CAS ]
  • [ 40181-00-8 ]
YieldReaction ConditionsOperation in experiment
4.76 g With zinc(II) chloride In toluene at 110℃; for 1h;
  • 31
  • [ 40181-00-8 ]
  • [ 949892-17-5 ]
  • 2-(3,4-dimethoxyphenyl)-1-(2-methoxy-4-(methoxymethoxy)phenyl)propan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: 1-bromo-2-methoxy-4-(methoxymethoxy)benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: 2-(3,4-di-methoxyphenyl)propionaldehyde In tetrahydrofuran; hexane at -78℃; for 1h; 1-1.2 Step 2] Synthesis of 2-(3,4-dimethoxyphenyl)-1-(2-methoxy-4- (methoxymethoxy)phenyl)propan-1-ol (3) To a solution of the aryl bromide (1056.6 mg, 4.28 mmol) in THF (22.5 mL) was added n-BuLi solution (1.6 M solution in n-hexane 2.5 mL, 4.00 mmol) was added dropwise at -78 °C The solution was stirred at -78 °C for 30 min and a solution of aldehyde in THF (10.0 mL) (A) (415.5 mg, 2.14 mmol). The reaction mixture was stirred at -78 °C for 1 hour. The reaction The mixture was washed with saturated NH4Cl solution and extracted with EtOAc. The combined organic layers were washed with brine, Dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel (EtOAc / n-hexane = 1: 3 to 1: 2) to give the secondary alcohol (557.0 mg, 72%) as a yellow solid.
72% Stage #1: 1-bromo-2-methoxy-4-(methoxymethoxy)benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 2-(3,4-di-methoxyphenyl)propionaldehyde In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
  • 32
  • [ 40181-00-8 ]
  • C22H26O6 [ No CAS ]
  • C22H26O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95 % ee With silver carbonate; (S)-2-[bis(3,5-dimethylphenyl)methyl]pyrrolidine; 4-nitro-benzoic acid In dichloromethane at 20℃; Inert atmosphere; Overall yield = 79 %; Overall yield = 30.5 mg; stereoselective reaction;
  • 33
  • [ 40181-00-8 ]
  • C22H26O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With silver carbonate; 4-nitro-benzoic acid In dichloromethane Inert atmosphere;
  • 34
  • [ 585-76-2 ]
  • [ 40181-00-8 ]
  • C18H17BrO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With silver carbonate In dichloromethane at 20℃; for 3h; Inert atmosphere; Alkaline conditions;
  • 35
  • [ 585-76-2 ]
  • [ 40181-00-8 ]
  • C18H17BrO5 [ No CAS ]
  • C18H17BrO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83 % ee With (S)-3,3-dimethyl-1-morpholinobutan-2-amine; silver carbonate In dichloromethane at 20℃; for 3h; Inert atmosphere; Overall yield = 93 %; enantioselective reaction;
  • 36
  • [ 40181-00-8 ]
  • [ 1415577-49-9 ]
  • C23H26O3S [ No CAS ]
  • C23H26O3S [ No CAS ]
  • C23H26O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
73 % ee Stage #1: 2-(3,4-di-methoxyphenyl)propionaldehyde With benzylamine In dimethyl sulfoxide; 1,2-dichloro-ethane at 0 - 20℃; for 1.25h; Molecular sieve; Stage #2: C12H14OS With dodecyl (R)-4-(N-prolylsulfamoyl)benzoate In dimethyl sulfoxide; 1,2-dichloro-ethane at 20℃; for 96h; Molecular sieve;
  • 37
  • [ 106-37-6 ]
  • [ 40181-00-8 ]
  • C17H19BrO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 2-(3,4-di-methoxyphenyl)propionaldehyde In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
  • 38
  • [ 40181-00-8 ]
  • 1-(4-bromophenyl)-2-(3,4-dimethoxyphenyl)propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
  • 39
  • [ 40181-00-8 ]
  • 2-(3,4-dimethoxyphenyl)-1-(4-(pyrrolidin-1-yl)phenyl)propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere 3.1: palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 20 - 100 °C / Inert atmosphere
  • 40
  • [ 40181-00-8 ]
  • [ 62-31-7 ]
  • [ 76-05-1 ]
  • (1S,1’R)-((5’,6’-dimethoxyphenyl)ethyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol*TFA [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% Stage #1: 2-(3,4-di-methoxyphenyl)propionaldehyde; dopamine hydrochloride With M97V variant of Δ29-Thalictrum flavum norcoclaurine synthase; sodium L-ascorbate In aq. phosphate buffer; acetonitrile at 37℃; for 18h; Enzymatic reaction; Stage #2: trifluoroacetic acid In water; acetonitrile
  • 41
  • [ 40181-00-8 ]
  • [ 62-31-7 ]
  • [ 76-05-1 ]
  • (1S,1’R)-((5’,6’-dimethoxyphenyl)ethyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol*TFA [ No CAS ]
  • ((5’,6’-dimethoxyphenyl)ethyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol*TFA [ No CAS ]
YieldReaction ConditionsOperation in experiment
74 % de Stage #1: 2-(3,4-di-methoxyphenyl)propionaldehyde; dopamine hydrochloride With L76V variant of Δ29-Thalictrum flavum norcoclaurine synthase; sodium L-ascorbate In aq. phosphate buffer; acetonitrile at 37℃; for 18h; Enzymatic reaction; Stage #2: trifluoroacetic acid In water; acetonitrile
  • 42
  • [ 40181-00-8 ]
  • [ 554-52-9 ]
  • [ 76-05-1 ]
  • ((1S,1’R)-(5’,6’-dimethoxyphenyl)ethyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol*TFA [ No CAS ]
  • ((5’,6’-dimethoxyphenyl)ethyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol*TFA [ No CAS ]
YieldReaction ConditionsOperation in experiment
84 % de Stage #1: 2-(3,4-di-methoxyphenyl)propionaldehyde; 3-Methoxytyramine With M97V variant of Δ29-Thalictrum flavum norcoclaurine synthase; sodium L-ascorbate In aq. phosphate buffer; acetonitrile at 37℃; for 18h; Enzymatic reaction; Stage #2: trifluoroacetic acid In water; acetonitrile Overall yield = 81 percent; Overall yield = 35.5 mg;
  • 43
  • [ 40181-01-9 ]
  • [ 40181-00-8 ]
YieldReaction ConditionsOperation in experiment
47% Stage #1: 2-(3,4-dimethoxyphenyl)-1-propanol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.5h; Stage #2: With triethylamine In dichloromethane; dimethyl sulfoxide at -30 - 0℃; for 1h;
  • 44
  • [ 40181-00-8 ]
  • (1S,1’R)-((5’,6’-dimethoxyphenyl)ethyl)-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol*TFA [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: M97V variant of Δ29-Thalictrum flavum norcoclaurine synthase; sodium L-ascorbate / aq. phosphate buffer; acetonitrile / 18 h / 37 °C / Enzymatic reaction 2: regioselective O-methyltransferase isolated from Rattus norvegicus; methionine adenosyltransferase from Escherichia coli; methylthioadenosine-SAH nucleosidase; ATP; L-methionine / aq. phosphate buffer; water / 37 °C / Enzymatic reaction
Multi-step reaction with 2 steps 1: sodium L-ascorbate; L76V variant of Δ29-Thalictrum flavum norcoclaurine synthase / aq. phosphate buffer; acetonitrile / 18 h / 37 °C / Enzymatic reaction 2: regioselective O-methyltransferase isolated from Rattus norvegicus; methionine adenosyltransferase from Escherichia coli; methylthioadenosine-SAH nucleosidase; ATP; L-methionine / aq. phosphate buffer; water / 37 °C / Enzymatic reaction
  • 45
  • [ 40181-00-8 ]
  • (13R,13aS)-9,10-dimethoxy-13-methyl-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-2,3-diol*TFA [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: M97V variant of Δ29-Thalictrum flavum norcoclaurine synthase; sodium L-ascorbate / aq. phosphate buffer; acetonitrile / 18 h / 37 °C / Enzymatic reaction 2: formic acid / water / 2 h / 50 °C
Multi-step reaction with 2 steps 1: sodium L-ascorbate; L76V variant of Δ29-Thalictrum flavum norcoclaurine synthase / aq. phosphate buffer; acetonitrile / 18 h / 37 °C / Enzymatic reaction 2: formic acid / water / 2 h / 50 °C
  • 46
  • [ 40181-00-8 ]
  • (13R,13aS)-3,10,11-trimethoxy-13-methyl-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinolin-2-ol*TFA [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: M97V variant of Δ29-Thalictrum flavum norcoclaurine synthase; sodium L-ascorbate / aq. phosphate buffer; acetonitrile / 18 h / 37 °C / Enzymatic reaction 2: regioselective O-methyltransferase isolated from Rattus norvegicus; methionine adenosyltransferase from Escherichia coli; methylthioadenosine-SAH nucleosidase; ATP; L-methionine / aq. phosphate buffer; water / 37 °C / Enzymatic reaction 3: formic acid / water / 2 h / 50 °C
Multi-step reaction with 3 steps 1: sodium L-ascorbate; L76V variant of Δ29-Thalictrum flavum norcoclaurine synthase / aq. phosphate buffer; acetonitrile / 18 h / 37 °C / Enzymatic reaction 2: regioselective O-methyltransferase isolated from Rattus norvegicus; methionine adenosyltransferase from Escherichia coli; methylthioadenosine-SAH nucleosidase; ATP; L-methionine / aq. phosphate buffer; water / 37 °C / Enzymatic reaction 3: formic acid / water / 2 h / 50 °C
  • 47
  • [ 40181-00-8 ]
  • 2-hydroxy-3,10,11-trimethoxy-13-methyl-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: M97V variant of Δ29-Thalictrum flavum norcoclaurine synthase; sodium L-ascorbate / aq. phosphate buffer; acetonitrile / 18 h / 37 °C / Enzymatic reaction 2: regioselective O-methyltransferase isolated from Rattus norvegicus; methionine adenosyltransferase from Escherichia coli; methylthioadenosine-SAH nucleosidase; ATP; L-methionine / aq. phosphate buffer; water / 37 °C / Enzymatic reaction 3: N,N-dimethyl-formamide / 18 h / 120 °C
Multi-step reaction with 3 steps 1: sodium L-ascorbate; L76V variant of Δ29-Thalictrum flavum norcoclaurine synthase / aq. phosphate buffer; acetonitrile / 18 h / 37 °C / Enzymatic reaction 2: regioselective O-methyltransferase isolated from Rattus norvegicus; methionine adenosyltransferase from Escherichia coli; methylthioadenosine-SAH nucleosidase; ATP; L-methionine / aq. phosphate buffer; water / 37 °C / Enzymatic reaction 3: N,N-dimethyl-formamide / 18 h / 120 °C
Multi-step reaction with 4 steps 1: M97V variant of Δ29-Thalictrum flavum norcoclaurine synthase; sodium L-ascorbate / aq. phosphate buffer; acetonitrile / 18 h / 37 °C / Enzymatic reaction 2: regioselective O-methyltransferase isolated from Rattus norvegicus; methionine adenosyltransferase from Escherichia coli; methylthioadenosine-SAH nucleosidase; ATP; L-methionine / aq. phosphate buffer; water / 37 °C / Enzymatic reaction 3: formic acid / water / 2 h / 50 °C 4: N,N-dimethyl-formamide / 18 h / 120 °C
Multi-step reaction with 4 steps 1: sodium L-ascorbate; L76V variant of Δ29-Thalictrum flavum norcoclaurine synthase / aq. phosphate buffer; acetonitrile / 18 h / 37 °C / Enzymatic reaction 2: regioselective O-methyltransferase isolated from Rattus norvegicus; methionine adenosyltransferase from Escherichia coli; methylthioadenosine-SAH nucleosidase; ATP; L-methionine / aq. phosphate buffer; water / 37 °C / Enzymatic reaction 3: formic acid / water / 2 h / 50 °C 4: N,N-dimethyl-formamide / 18 h / 120 °C

  • 48
  • [ 6380-23-0 ]
  • [ 201230-82-2 ]
  • [ 40181-00-8 ]
YieldReaction ConditionsOperation in experiment
36% With 1,3-bis-(diphenylphosphino)propane; hydrogen; copper(l) cyanide; sodium t-butanolate In toluene at 100℃; for 20h; regioselective reaction;
  • 49
  • [ 93-16-3 ]
  • [ 40181-00-8 ]
  • [ 61871-67-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: [1,3-bis(2,6-di-isopropylphenyl)-2-imidazolidinylidene]dichloro(o-isopropoxyphenylmethylene)ruthenium(II) / toluene / 2 h / 60 °C / 3750.38 Torr / Schlenk technique; Glovebox 2: tris(2,4-di-tert-butylphenyl)phosphite; hydrogen; methoxy(cyclooctadiene)rhodium(I) dimer / toluene / 4 h / 60 °C / 30003 Torr / Schlenk technique; Glovebox
  • 50
  • [ 40181-00-8 ]
  • [ 1192280-95-7 ]
  • [ 1386351-18-3 ]
YieldReaction ConditionsOperation in experiment
86 % ee With tris[2-phenylpyridinato-C2,N]iridium(III); C10H24N2; bis(trifluoromethanesulfonyl)amide; benzoic acid In acetonitrile at 0℃; for 1h; Irradiation; Inert atmosphere; Resolution of racemate; Overall yield = 78 percent; enantioselective reaction;
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