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[ CAS No. 51234-09-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 51234-09-4
Chemical Structure| 51234-09-4
Chemical Structure| 51234-09-4
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Product Details of [ 51234-09-4 ]

CAS No. :51234-09-4 MDL No. :MFCD03428551
Formula : C10H12O3 Boiling Point : -
Linear Structure Formula :- InChI Key :SDPDVKKZRJAMEK-UHFFFAOYSA-N
M.W : 180.20 Pubchem ID :11586390
Synonyms :

Calculated chemistry of [ 51234-09-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.78
TPSA : 35.53 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) : -6.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.02
Log Po/w (XLOGP3) : 1.69
Log Po/w (WLOGP) : 1.82
Log Po/w (MLOGP) : 1.13
Log Po/w (SILICOS-IT) : 2.47
Consensus Log Po/w : 1.83

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.17
Solubility : 1.23 mg/ml ; 0.00683 mol/l
Class : Soluble
Log S (Ali) : -2.05
Solubility : 1.6 mg/ml ; 0.00889 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.99
Solubility : 0.186 mg/ml ; 0.00103 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.44

Safety of [ 51234-09-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P310-P312-P330-P332+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H312-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 51234-09-4 ]

* 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 [ 51234-09-4 ]

[ 51234-09-4 ] Synthesis Path-Downstream   1~96

  • 1
  • [ 79-24-3 ]
  • [ 51234-09-4 ]
  • [ 139122-90-0 ]
YieldReaction ConditionsOperation in experiment
With ammonium acetate; acetic acid
  • 2
  • [ 75-52-5 ]
  • [ 51234-09-4 ]
  • [ 80547-81-5 ]
YieldReaction ConditionsOperation in experiment
64% With ammonium acetate In acetic acid for 2h; Heating;
With ammonium acetate; acetic acid
  • 3
  • [ 5417-19-6 ]
  • [ 51234-09-4 ]
YieldReaction ConditionsOperation in experiment
With chloroform; hexamethylenetetramine beim Erwaermen des Reaktionsprodukts mit wss. Essigsaeure;
  • 4
  • [ 51234-09-4 ]
  • [ 109962-81-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogen bromide
  • 5
  • [ 51234-09-4 ]
  • [ 5722-94-1 ]
YieldReaction ConditionsOperation in experiment
With potassium permanganate In acetone
  • 6
  • [ 4885-02-3 ]
  • [ 4463-33-6 ]
  • [ 51234-09-4 ]
YieldReaction ConditionsOperation in experiment
95% With tin(IV) chloride In dichloromethane a) 0 deg C, 1 h, b) 0 deg C, 1 h, c) to room temperature;
With titanium tetrachloride In dichloromethane at 25℃; for 2h;
  • 7
  • [ 51234-09-4 ]
  • [ 1100-88-5 ]
  • [ 144412-67-9 ]
  • [ 144412-66-8 ]
YieldReaction ConditionsOperation in experiment
With sodium ethanolate 1) ethanol, room temperature, 10 min, 2) ethanol, room temperature, 2 h; Yield given. Multistep reaction. Yields of byproduct given;
  • 8
  • [ 51234-09-4 ]
  • [ 88122-12-7 ]
YieldReaction ConditionsOperation in experiment
94% With water; boron tribromide In dichloromethane
With boron tribromide In dichloromethane 1.) -78 deg C, 30 min, 2.) 25 deg C, 2 h;
  • 9
  • [ 80547-78-0 ]
  • [ 51234-09-4 ]
YieldReaction ConditionsOperation in experiment
88% With pyridinium chlorochromate In dichloromethane for 1h; Ambient temperature;
  • 10
  • [ 51234-09-4 ]
  • [ 80547-78-0 ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride In diethyl ether Ambient temperature;
  • 11
  • [ 88122-12-7 ]
  • [ 77-78-1 ]
  • [ 51234-09-4 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In water at 100℃;
  • 12
  • [1-(3,4-Dimethoxy-2-methyl-phenyl)-meth-(E)-ylidene]-(1-isopropyl-2-methyl-propyl)-amine [ No CAS ]
  • [ 51234-09-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In tetrahydrofuran Heating; Yield given;
YieldReaction ConditionsOperation in experiment
With potassium permanganate; acetone
  • 14
  • [ 141-82-2 ]
  • [ 51234-09-4 ]
  • [ 184850-56-4 ]
YieldReaction ConditionsOperation in experiment
With piperidine; pyridine at 100 - 140℃; for 2h;
  • 15
  • [ 51234-09-4 ]
  • ethyl 3-(2-bromomethyl-3,4-dimethoxyphenyl)-2-propenoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine; piperidine / 2 h / 100 - 140 °C 2: H2SO4 / 2 h / Heating 3: 6.22 g / N-bromosuccinimide; benzoyl peroxide / CCl4 / 8 h / Heating
  • 16
  • [ 51234-09-4 ]
  • [ 868562-32-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: pyridine; piperidine / 2 h / 100 - 140 °C 2: H2SO4 / 2 h / Heating 3: 6.22 g / N-bromosuccinimide; benzoyl peroxide / CCl4 / 8 h / Heating 4: 90 percent / dimethylformamide / 1.5 h / 20 °C 5: 92.8 percent / HCl / 1 h / Heating 6: 94 percent / H2 / Pd/C / ethanol; CH2Cl2 / 20 °C / ambient pressure 7: 55 percent / potassium tert-butoxide / benzene / 0.5 h / Heating
  • 17
  • [ 51234-09-4 ]
  • ethyl 3-(2-cyanomethyl-3,4-dimethoxyphenyl)-2-propenoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: pyridine; piperidine / 2 h / 100 - 140 °C 2: H2SO4 / 2 h / Heating 3: 6.22 g / N-bromosuccinimide; benzoyl peroxide / CCl4 / 8 h / Heating 4: 90 percent / dimethylformamide / 1.5 h / 20 °C
  • 18
  • [ 51234-09-4 ]
  • ethyl 3-(3,4-dimethoxy-2-(ethoxycarbonylmethyl)phenyl)-2-propenoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: pyridine; piperidine / 2 h / 100 - 140 °C 2: H2SO4 / 2 h / Heating 3: 6.22 g / N-bromosuccinimide; benzoyl peroxide / CCl4 / 8 h / Heating 4: 90 percent / dimethylformamide / 1.5 h / 20 °C 5: 92.8 percent / HCl / 1 h / Heating
  • 19
  • [ 51234-09-4 ]
  • [ 868562-31-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: pyridine; piperidine / 2 h / 100 - 140 °C 2: H2SO4 / 2 h / Heating 3: 6.22 g / N-bromosuccinimide; benzoyl peroxide / CCl4 / 8 h / Heating 4: 90 percent / dimethylformamide / 1.5 h / 20 °C 5: 92.8 percent / HCl / 1 h / Heating 6: 94 percent / H2 / Pd/C / ethanol; CH2Cl2 / 20 °C / ambient pressure
  • 20
  • [ 51234-09-4 ]
  • [ 90266-15-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: pyridine; piperidine / 2 h / 100 - 140 °C 2: H2SO4 / 2 h / Heating 3: 6.22 g / N-bromosuccinimide; benzoyl peroxide / CCl4 / 8 h / Heating 4: 90 percent / dimethylformamide / 1.5 h / 20 °C 5: 92.8 percent / HCl / 1 h / Heating 6: 94 percent / H2 / Pd/C / ethanol; CH2Cl2 / 20 °C / ambient pressure 7: 55 percent / potassium tert-butoxide / benzene / 0.5 h / Heating 8: 73 percent / sodium chloride; water / dimethylsulfoxide / 2.5 h / 150 °C
  • 21
  • [1-(3,4-Dimethoxy-phenyl)-meth-(E)-ylidene]-(1-isopropyl-2-methyl-propyl)-amine [ No CAS ]
  • [ 51234-09-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1) ether, hexane, -78 deg C --> rt; 2) ether, hexane, -78 deg C --> rt 2: aq. HCl / tetrahydrofuran / Heating
  • 22
  • [ 58343-46-7 ]
  • [ 51234-09-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: BCl3*SMe2 / 1,2-dichloro-ethane / 83 °C 2: NaOH / H2O / 100 °C
  • 23
  • [ 51234-09-4 ]
  • (6-Bromo-3,4-dimethoxy-2-methyl-phenyl)-methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: LiAlH4 / diethyl ether / Ambient temperature 2: DMAP, pyridine / CH2Cl2 / Ambient temperature 3: Br2 / acetic acid / Ambient temperature 4: K2CO3 / methanol; tetrahydrofuran / Ambient temperature
  • 24
  • [ 51234-09-4 ]
  • [ 173040-53-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: LiAlH4 / diethyl ether / Ambient temperature 2: DMAP, pyridine / CH2Cl2 / Ambient temperature 3: Br2 / acetic acid / Ambient temperature 4: K2CO3 / methanol; tetrahydrofuran / Ambient temperature 5: Dess-Martin periodinane / CH2Cl2 / Ambient temperature
  • 25
  • [ 51234-09-4 ]
  • Acetic acid 3,4-dimethoxy-2-methyl-benzyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether / Ambient temperature 2: DMAP, pyridine / CH2Cl2 / Ambient temperature
  • 26
  • [ 51234-09-4 ]
  • Acetic acid 6-bromo-3,4-dimethoxy-2-methyl-benzyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: LiAlH4 / diethyl ether / Ambient temperature 2: DMAP, pyridine / CH2Cl2 / Ambient temperature 3: Br2 / acetic acid / Ambient temperature
  • 27
  • [ 51234-09-4 ]
  • (S)-1-(6-Bromo-3,4-dimethoxy-2-methyl-phenyl)-3-phenyl-butan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: LiAlH4 / diethyl ether / Ambient temperature 2: DMAP, pyridine / CH2Cl2 / Ambient temperature 3: Br2 / acetic acid / Ambient temperature 4: K2CO3 / methanol; tetrahydrofuran / Ambient temperature 5: Dess-Martin periodinane / CH2Cl2 / Ambient temperature 6: 78 percent / 1.) Mg / tetrahydrofuran / 1.) RT down to 0 deg C, 0.5 h; 2.) 0 deg C 7: (COCl)2/DMSO, Et3N / CH2Cl2 / 1 h / -78 deg C up to RT
  • 28
  • [ 51234-09-4 ]
  • (S)-1-(6-Bromo-3,4-dimethoxy-2-methyl-phenyl)-3-phenyl-butan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: LiAlH4 / diethyl ether / Ambient temperature 2: DMAP, pyridine / CH2Cl2 / Ambient temperature 3: Br2 / acetic acid / Ambient temperature 4: K2CO3 / methanol; tetrahydrofuran / Ambient temperature 5: Dess-Martin periodinane / CH2Cl2 / Ambient temperature 6: 78 percent / 1.) Mg / tetrahydrofuran / 1.) RT down to 0 deg C, 0.5 h; 2.) 0 deg C
  • 29
  • [ 51234-09-4 ]
  • [ 173040-54-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: LiAlH4 / diethyl ether / Ambient temperature 2: DMAP, pyridine / CH2Cl2 / Ambient temperature 3: Br2 / acetic acid / Ambient temperature 4: K2CO3 / methanol; tetrahydrofuran / Ambient temperature 5: Dess-Martin periodinane / CH2Cl2 / Ambient temperature 6: 78 percent / 1.) Mg / tetrahydrofuran / 1.) RT down to 0 deg C, 0.5 h; 2.) 0 deg C 7: (COCl)2/DMSO, Et3N / CH2Cl2 / 1 h / -78 deg C up to RT 8: TMSOTf / CH2Cl2 / 4 h / -78 °C
  • 30
  • [ 51234-09-4 ]
  • C21H26O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: LiAlH4 / diethyl ether / Ambient temperature 2: DMAP, pyridine / CH2Cl2 / Ambient temperature 3: Br2 / acetic acid / Ambient temperature 4: K2CO3 / methanol; tetrahydrofuran / Ambient temperature 5: Dess-Martin periodinane / CH2Cl2 / Ambient temperature 6: 78 percent / 1.) Mg / tetrahydrofuran / 1.) RT down to 0 deg C, 0.5 h; 2.) 0 deg C 7: (COCl)2/DMSO, Et3N / CH2Cl2 / 1 h / -78 deg C up to RT 8: TMSOTf / CH2Cl2 / 4 h / -78 °C 9: 1.) 0.1M LDA / tetrahydrofuran / 1.) -78 deg C, 2 h; 2.) up to RT over 12 h
  • 31
  • [ 51234-09-4 ]
  • [ 173040-55-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: LiAlH4 / diethyl ether / Ambient temperature 2: DMAP, pyridine / CH2Cl2 / Ambient temperature 3: Br2 / acetic acid / Ambient temperature 4: K2CO3 / methanol; tetrahydrofuran / Ambient temperature 5: Dess-Martin periodinane / CH2Cl2 / Ambient temperature 6: 78 percent / 1.) Mg / tetrahydrofuran / 1.) RT down to 0 deg C, 0.5 h; 2.) 0 deg C 7: (COCl)2/DMSO, Et3N / CH2Cl2 / 1 h / -78 deg C up to RT 8: TMSOTf / CH2Cl2 / 4 h / -78 °C 9: 1.) 0.1M LDA / tetrahydrofuran / 1.) -78 deg C, 2 h; 2.) up to RT over 12 h
  • 32
  • [ 51234-09-4 ]
  • [ 97073-43-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: BBr3 / CH2Cl2 / 1.) -78 deg C, 30 min, 2.) 25 deg C, 2 h 2: 76 percent / KI, K2CO3 / acetone / 7 h / Heating
  • 33
  • [ 51234-09-4 ]
  • [ 97102-11-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: BBr3 / CH2Cl2 / 1.) -78 deg C, 30 min, 2.) 25 deg C, 2 h 2: 76 percent / KI, K2CO3 / acetone / 7 h / Heating 3: 86 percent / NH4OAc / acetic acid / 1.5 h / Heating 4: 82 percent / 90percent HNO3 / acetic acid / 2.5 h / Ambient temperature 5: 96 percent / silica gel, Fe / acetic acid; toluene / 1 h / Heating
  • 34
  • [ 51234-09-4 ]
  • [ 97073-54-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: BBr3 / CH2Cl2 / 1.) -78 deg C, 30 min, 2.) 25 deg C, 2 h 2: 76 percent / KI, K2CO3 / acetone / 7 h / Heating 3: 86 percent / NH4OAc / acetic acid / 1.5 h / Heating 4: 82 percent / 90percent HNO3 / acetic acid / 2.5 h / Ambient temperature 5: 96 percent / silica gel, Fe / acetic acid; toluene / 1 h / Heating 6: acetic acid / ethanol; H2O / 14 h / 0 - 25 °C
  • 35
  • [ 51234-09-4 ]
  • [ 97073-46-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: BBr3 / CH2Cl2 / 1.) -78 deg C, 30 min, 2.) 25 deg C, 2 h 2: 76 percent / KI, K2CO3 / acetone / 7 h / Heating 3: 86 percent / NH4OAc / acetic acid / 1.5 h / Heating
  • 36
  • [ 51234-09-4 ]
  • [ 97073-49-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: BBr3 / CH2Cl2 / 1.) -78 deg C, 30 min, 2.) 25 deg C, 2 h 2: 76 percent / KI, K2CO3 / acetone / 7 h / Heating 3: 86 percent / NH4OAc / acetic acid / 1.5 h / Heating 4: 82 percent / 90percent HNO3 / acetic acid / 2.5 h / Ambient temperature
  • 37
  • [ 4463-33-6 ]
  • [ 51234-09-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 70 percent / polyphosphoric acid / 1.5 h / 45 - 50 °C 2: 81.5 percent / aq. NaOCl / 0.67 h / 60 - 70 °C 3: 74 percent / LiAlH4 / tetrahydrofuran / 12 h / Heating 4: 88 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature
  • 38
  • [ 5417-20-9 ]
  • [ 51234-09-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 81.5 percent / aq. NaOCl / 0.67 h / 60 - 70 °C 2: 74 percent / LiAlH4 / tetrahydrofuran / 12 h / Heating 3: 88 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature
  • 39
  • [ 5722-94-1 ]
  • [ 51234-09-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 74 percent / LiAlH4 / tetrahydrofuran / 12 h / Heating 2: 88 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature
  • 40
  • [ 51234-09-4 ]
  • [ 80547-74-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 64 percent / ammonium acetate / acetic acid / 2 h / Heating 2: 85 percent / conc. HNO3 / acetic acid / 3 h / Ambient temperature 3: 37 percent / Fe, glacial acetic acid / 2 h / Heating 4: 37 percent / 48percent HBr / 0.25 h / Heating
  • 41
  • [ 51234-09-4 ]
  • [ 80547-84-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 64 percent / ammonium acetate / acetic acid / 2 h / Heating 2: 85 percent / conc. HNO3 / acetic acid / 3 h / Ambient temperature 3: 37 percent / Fe, glacial acetic acid / 2 h / Heating
  • 42
  • [ 51234-09-4 ]
  • [ 80547-82-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 64 percent / ammonium acetate / acetic acid / 2 h / Heating 2: 85 percent / conc. HNO3 / acetic acid / 3 h / Ambient temperature
  • 43
  • [ 488-17-5 ]
  • [ 51234-09-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 83 percent / K2CO3 / acetone / 3 h / Heating 2: 70 percent / polyphosphoric acid / 1.5 h / 45 - 50 °C 3: 81.5 percent / aq. NaOCl / 0.67 h / 60 - 70 °C 4: 74 percent / LiAlH4 / tetrahydrofuran / 12 h / Heating 5: 88 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature
  • 44
  • [ 51234-09-4 ]
  • [ 102447-10-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: acetic acid; ammonium acetate 2: diethyl ether; LiAlH4 3: Na2CO3; benzene 4: phosphoryl chloride; benzene
  • 45
  • [ 51234-09-4 ]
  • 1-isopropyl-6,7-dimethoxy-5-methyl-1,2,3,4-tetrahydro-isoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: acetic acid; ammonium acetate 2: diethyl ether; LiAlH4 3: Na2CO3; benzene 4: phosphoryl chloride; benzene 5: diethyl ether; lithium alanate
  • 46
  • [ 51234-09-4 ]
  • [ 77200-86-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid; ammonium acetate 2: diethyl ether; LiAlH4
  • 47
  • [ 51234-09-4 ]
  • [ 104216-17-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aqueous HBr
  • 48
  • [ 51234-09-4 ]
  • [ 101108-58-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetic acid; ammonium acetate 2: diethyl ether; LiAlH4 3: Na2CO3; benzene
  • 49
  • [ 51234-09-4 ]
  • [ 98959-87-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetic acid; ammonium acetate 2: diethyl ether; LiAlH4 3: water; HBr
  • 50
  • [ 51234-09-4 ]
  • [ 15364-84-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aq. KMnO4 / acetone 2: H2SO4
  • 51
  • [ 51234-09-4 ]
  • [ 15365-27-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: aq. KMnO4 / acetone 2: H2SO4 3: NBS, (PhCO)2O2 / CCl4
  • 52
  • [ 51234-09-4 ]
  • [ 15365-32-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: aq. KMnO4 / acetone 2: H2SO4 3: NBS, (PhCO)2O2 / CCl4 4: Et3N / diethyl ether
  • 53
  • [ 74866-17-4 ]
  • [ 68-12-2 ]
  • [ 51234-09-4 ]
  • 54
  • [ 51234-09-4 ]
  • [ 106-65-0 ]
  • [ 1160440-49-2 ]
YieldReaction ConditionsOperation in experiment
With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 20℃; 1.2 EXAMPLE 1.2Preparation of 4,6,7-trimethoxy-8-methyl-2-naphthoic acid (Compound 4)4,6,7-Trimethoxy-8-methyl-2-naphthoic acid (7) is prepared in six steps according to the following reaction diagram. Reduction of 3,4-dimethoxy-2-methylbenzoic acid (1) to aldehyde (2) can be carried out by the Rosenmund reaction (SOCl2 then H2, Pd/BaSO4) (see reference 27). The aldehyde (2) is then reacted with dimethyl succinate (Stobbe reaction) (see reference 28). The coupling product (3) is not isolated but is treated directly with sodium acetate in the presence of acetic anhydride and acetic acid (AcOH/Ac2O 1:1) to give 4. After saponification, 4-hydroxy-6,7-dimethoxy-8-methyl-2-naphthoic acid (5) is obtained with a yield of 70% (3 steps). After esterification under the conditions described above (90%), compound 6 is hydrolysed to give 4,6,7-trimethoxy-8-methyl-2-naphthoic acid (7) (92%).
  • 55
  • C10H11ClO3 [ No CAS ]
  • [ 51234-09-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogen 1.2 EXAMPLE 1.2Preparation of 4,6,7-trimethoxy-8-methyl-2-naphthoic acid (Compound 4)4,6,7-Trimethoxy-8-methyl-2-naphthoic acid (7) is prepared in six steps according to the following reaction diagram. Reduction of 3,4-dimethoxy-2-methylbenzoic acid (1) to aldehyde (2) can be carried out by the Rosenmund reaction (SOCl2 then H2, Pd/BaSO4) (see reference 27). The aldehyde (2) is then reacted with dimethyl succinate (Stobbe reaction) (see reference 28). The coupling product (3) is not isolated but is treated directly with sodium acetate in the presence of acetic anhydride and acetic acid (AcOH/Ac2O 1:1) to give 4. After saponification, 4-hydroxy-6,7-dimethoxy-8-methyl-2-naphthoic acid (5) is obtained with a yield of 70% (3 steps). After esterification under the conditions described above (90%), compound 6 is hydrolysed to give 4,6,7-trimethoxy-8-methyl-2-naphthoic acid (7) (92%).
  • 56
  • [ 5722-94-1 ]
  • [ 51234-09-4 ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: 2-methyl-3,4-dimethoxybenzoic acid With lithium aluminium tetrahydride In tetrahydrofuran Stage #2: With pyridinium chlorochromate
  • 57
  • [ 51234-09-4 ]
  • [ 1261383-34-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: potassium carbonate / acetone / 24 h / 20 °C 4.1: potassium hydroxide / water / Reflux 5.1: 2,2,6,6-tetramethylpiperidinyl-lithium / tetrahydrofuran / 0 - 20 °C 5.2: 2 h / 20 °C
  • 58
  • [ 51234-09-4 ]
  • [ 1261383-36-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: potassium carbonate / acetone / 24 h / 20 °C 4.1: potassium hydroxide / water / Reflux 5.1: 2,2,6,6-tetramethylpiperidinyl-lithium / tetrahydrofuran / 0 - 20 °C 5.2: 2 h / 20 °C
  • 59
  • [ 51234-09-4 ]
  • [ 1160440-66-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: potassium carbonate / acetone / 24 h / 20 °C 4.1: potassium hydroxide / water / Reflux 5.1: 2,2,6,6-tetramethylpiperidinyl-lithium / tetrahydrofuran / 3 h / -78 - 20 °C
  • 60
  • [ 51234-09-4 ]
  • [ 1261383-14-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: n-butyllithium / tetrahydrofuran / -78 °C 3.2: 0.25 h / 0 °C 3.3: 1 h / 0 °C
  • 61
  • [ 51234-09-4 ]
  • [ 1261383-40-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: n-butyllithium / tetrahydrofuran / -78 °C 3.2: 0.25 h / 0 °C 3.3: 2 h / 0 °C
  • 62
  • [ 51234-09-4 ]
  • [ 1261383-42-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: n-butyllithium / tetrahydrofuran / -78 °C 3.2: 0.25 h / 0 °C 3.3: 3 h / 0 °C
  • 63
  • [ 51234-09-4 ]
  • [ 1261383-44-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: n-butyllithium / tetrahydrofuran / -78 °C 3.2: 0.25 h / 0 °C 3.3: 3 h / 0 °C
  • 64
  • [ 51234-09-4 ]
  • [ 1160440-57-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: lithium aluminium tetrahydride / tetrahydrofuran / Reflux
  • 65
  • [ 51234-09-4 ]
  • [ 1261383-22-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: n-butyllithium / tetrahydrofuran / -78 °C 3.2: 0.25 h / 0 °C 3.3: 1 h / 0 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 30 °C
  • 66
  • [ 51234-09-4 ]
  • [ 1261383-47-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: n-butyllithium / tetrahydrofuran / -78 °C 3.2: 0.25 h / 0 °C 3.3: 2 h / 0 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 30 °C
  • 67
  • [ 51234-09-4 ]
  • [ 1261383-50-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: n-butyllithium / tetrahydrofuran / -78 °C 3.2: 0.25 h / 0 °C 3.3: 3 h / 0 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 30 °C
  • 68
  • [ 51234-09-4 ]
  • [ 1261383-53-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: n-butyllithium / tetrahydrofuran / -78 °C 3.2: 0.25 h / 0 °C 3.3: 3 h / 0 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 30 °C
  • 69
  • [ 51234-09-4 ]
  • [ 1160440-58-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: lithium aluminium tetrahydride / tetrahydrofuran / Reflux 4.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; water / 0.17 h / 25 °C / 2625.26 Torr
  • 70
  • [ 51234-09-4 ]
  • [ 1261383-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: n-butyllithium / tetrahydrofuran / -78 °C 3.2: 0.25 h / 0 °C 3.3: 1 h / 0 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 30 °C 5.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; water / 0.75 h / 25 °C / 2625.26 Torr
  • 71
  • [ 51234-09-4 ]
  • [ 1261383-55-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: n-butyllithium / tetrahydrofuran / -78 °C 3.2: 0.25 h / 0 °C 3.3: 2 h / 0 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 30 °C 5.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; water / 0.75 h / 25 °C / 2625.26 Torr
  • 72
  • [ 51234-09-4 ]
  • [ 1261383-57-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: n-butyllithium / tetrahydrofuran / -78 °C 3.2: 0.25 h / 0 °C 3.3: 3 h / 0 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 30 °C 5.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; water / 0.75 h / 25 °C / 2625.26 Torr
  • 73
  • [ 51234-09-4 ]
  • [ 1261383-59-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: n-butyllithium / tetrahydrofuran / -78 °C 3.2: 0.25 h / 0 °C 3.3: 3 h / 0 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 30 °C 5.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; water / 0.75 h / 25 °C / 2625.26 Torr
  • 74
  • [ 51234-09-4 ]
  • [ 1261383-31-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: lithium aluminium tetrahydride / tetrahydrofuran / Reflux 4.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; water / 24 h / 25 °C / 2025.2 Torr
  • 75
  • [ 51234-09-4 ]
  • [ 1160440-62-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: lithium aluminium tetrahydride / tetrahydrofuran / Reflux 4.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; water / 0.17 h / 25 °C / 2625.26 Torr 5.1: 200 °C
  • 76
  • [ 51234-09-4 ]
  • [ 1261383-29-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: n-butyllithium / tetrahydrofuran / -78 °C 3.2: 0.25 h / 0 °C 3.3: 1 h / 0 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 30 °C 5.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; water / 0.75 h / 25 °C / 2625.26 Torr 6.1: 200 °C
  • 77
  • [ 51234-09-4 ]
  • [ 1261383-61-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: n-butyllithium / tetrahydrofuran / -78 °C 3.2: 0.25 h / 0 °C 3.3: 2 h / 0 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 30 °C 5.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; water / 0.75 h / 25 °C / 2625.26 Torr 6.1: 200 °C
  • 78
  • [ 51234-09-4 ]
  • [ 1261383-63-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: n-butyllithium / tetrahydrofuran / -78 °C 3.2: 0.25 h / 0 °C 3.3: 3 h / 0 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 30 °C 5.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; water / 0.75 h / 25 °C / 2625.26 Torr 6.1: 200 °C
  • 79
  • [ 51234-09-4 ]
  • [ 1261383-65-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: n-butyllithium / tetrahydrofuran / -78 °C 3.2: 0.25 h / 0 °C 3.3: 3 h / 0 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 30 °C 5.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; water / 0.75 h / 25 °C / 2625.26 Torr 6.1: 200 °C
  • 80
  • [ 51234-09-4 ]
  • [ 1160440-60-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: lithium aluminium tetrahydride / tetrahydrofuran / Reflux 4.1: di-tert-butyl peroxide / chlorobenzene / 50 h / 105 °C
  • 81
  • [ 51234-09-4 ]
  • [ 1261383-12-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: lithium aluminium tetrahydride / tetrahydrofuran / Reflux 4.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; water / 0.17 h / 25 °C / 2625.26 Torr 5.1: 200 °C 6.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C 6.2: 1 h / 0 °C
  • 82
  • [ 51234-09-4 ]
  • [ 1261383-68-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: n-butyllithium / tetrahydrofuran / -78 °C 3.2: 0.25 h / 0 °C 3.3: 2 h / 0 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 30 °C 5.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; water / 0.75 h / 25 °C / 2625.26 Torr 6.1: 200 °C 7.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C 7.2: 1 h / 0 °C
  • 83
  • [ 51234-09-4 ]
  • [ 1261383-70-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: n-butyllithium / tetrahydrofuran / -78 °C 3.2: 0.25 h / 0 °C 3.3: 3 h / 0 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 30 °C 5.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; water / 0.75 h / 25 °C / 2625.26 Torr 6.1: 200 °C 7.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C 7.2: 1 h / 0 °C
  • 84
  • [ 51234-09-4 ]
  • [ 1261383-72-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: n-butyllithium / tetrahydrofuran / -78 °C 3.2: 0.25 h / 0 °C 3.3: 3 h / 0 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 30 °C 5.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; water / 0.75 h / 25 °C / 2625.26 Torr 6.1: 200 °C 7.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C 7.2: 1 h / 0 °C
  • 85
  • [ 51234-09-4 ]
  • [ 1160440-51-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux
  • 86
  • [ 51234-09-4 ]
  • [ 1160440-53-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: potassium carbonate / acetone / 24 h / 20 °C
  • 87
  • [ 51234-09-4 ]
  • [ 1160440-54-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: potassium carbonate / acetone / 24 h / 20 °C 4.1: potassium hydroxide / water / Reflux
  • 88
  • [ 51234-09-4 ]
  • [ 1160440-65-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: potassium carbonate / acetone / 24 h / 20 °C 4.1: potassium hydroxide / water / Reflux 5.1: 2,2,6,6-tetramethylpiperidinyl-lithium / tetrahydrofuran / 0 - 20 °C 5.2: 2 h / 20 °C
  • 89
  • [ 51234-09-4 ]
  • [ 96964-29-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 20 °C 2.1: acetic anhydride; sodium carbonate / acetic acid / Reflux 2.2: Reflux 3.1: n-butyllithium / tetrahydrofuran / -78 °C 3.2: 0.25 h / 0 °C 3.3: 1 h / 0 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 30 °C 5.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; water / 0.75 h / 25 °C / 2625.26 Torr 6.1: 200 °C 7.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C 7.2: 1 h / 0 °C
  • 90
  • [ 51234-09-4 ]
  • [ 106-65-0 ]
  • C16H20O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
10.26 g With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 20℃;
  • 91
  • [ 93-07-2 ]
  • [ 51234-09-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2,2,6,6-tetramethylpiperidinyl-lithium 2: lithium aluminium tetrahydride / tetrahydrofuran
  • 92
  • [ 51234-09-4 ]
  • [ 1407156-05-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: toluene / 2.5 h / Reflux; Dean-Stark 2: sodium tetrahydroborate / ethanol / 20 °C 3: pyridine / dichloromethane / 2 h / 20 °C / Cooling with ice 4: hydrogenchloride / water; 1,4-dioxane / 3 h / Reflux 5: boron tribromide / dichloromethane / 1 h / 20 °C / Cooling with ice
  • 93
  • [ 51234-09-4 ]
  • [ 1407156-06-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: toluene / 2.5 h / Reflux; Dean-Stark 2: sodium tetrahydroborate / ethanol / 20 °C 3: pyridine / dichloromethane / 2 h / 20 °C / Cooling with ice 4: hydrogenchloride / water; 1,4-dioxane / 3 h / Reflux 5: boron tribromide / dichloromethane / 1 h / 20 °C / Cooling with ice 6: ammonia / water / pH 8
  • 94
  • [ 51234-09-4 ]
  • [ 1407156-07-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: toluene / 2.5 h / Reflux; Dean-Stark 2: sodium tetrahydroborate / ethanol / 20 °C 3: pyridine / dichloromethane / 2 h / 20 °C / Cooling with ice 4: hydrogenchloride / water; 1,4-dioxane / 3 h / Reflux 5: boron tribromide / dichloromethane / 1 h / 20 °C / Cooling with ice 6: ammonia / water / pH 8 7: dmap / dichloromethane / 2 h / 20 °C
  • 95
  • [ 51234-09-4 ]
  • C59H69N10O13S2(1+)*I(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: toluene / 2.5 h / Reflux; Dean-Stark 2.1: sodium tetrahydroborate / ethanol / 20 °C 3.1: pyridine / dichloromethane / 2 h / 20 °C / Cooling with ice 4.1: hydrogenchloride / water; 1,4-dioxane / 3 h / Reflux 5.1: boron tribromide / dichloromethane / 1 h / 20 °C / Cooling with ice 6.1: ammonia / water / pH 8 7.1: dmap / dichloromethane / 2 h / 20 °C 8.1: sodium iodide / N,N-dimethyl-formamide / 6 h / 0 - 20 °C 8.2: 0.5 h / -40 °C
  • 96
  • [ 51234-09-4 ]
  • C27H25N10O7S2(1-)*Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: toluene / 2.5 h / Reflux; Dean-Stark 2.1: sodium tetrahydroborate / ethanol / 20 °C 3.1: pyridine / dichloromethane / 2 h / 20 °C / Cooling with ice 4.1: hydrogenchloride / water; 1,4-dioxane / 3 h / Reflux 5.1: boron tribromide / dichloromethane / 1 h / 20 °C / Cooling with ice 6.1: ammonia / water / pH 8 7.1: dmap / dichloromethane / 2 h / 20 °C 8.1: sodium iodide / N,N-dimethyl-formamide / 6 h / 0 - 20 °C 8.2: 0.5 h / -40 °C 9.1: methoxybenzene; aluminum (III) chloride / dichloromethane; nitromethane / 1 h / -40 - 0 °C 9.2: pH 6
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