Alternatived Products of [ 51234-09-4 ]
Product Details of [ 51234-09-4 ]
CAS No. : 51234-09-4
MDL No. : MFCD03428551
Formula :
C10 H12 O3
Boiling Point :
-
Linear Structure Formula : -
InChI Key : SDPDVKKZRJAMEK-UHFFFAOYSA-N
M.W : 180.20 g/mol
Pubchem ID : 11586390
Synonyms :
Calculated chemistry of [ 51234-09-4 ]
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
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 ]
1
[ 79-24-3 ]
[ 51234-09-4 ]
[ 139122-90-0 ]
Yield Reaction Conditions Operation in experiment
With ammonium acetate; acetic acid
2
[ 75-52-5 ]
[ 51234-09-4 ]
[ 80547-81-5 ]
Yield Reaction Conditions Operation in experiment
64%
With ammonium acetate In acetic acid for 2h; Heating;
With ammonium acetate; acetic acid
Reference:
[1]Borchardt, Ronald T.; Bhatia, Pramila
[Journal of Medicinal Chemistry, 1982, vol. 25, # 3, p. 263 - 271]
[2]Burger; Foggio
[Journal of the American Chemical Society, 1956, vol. 78, p. 4419,4422]
3
[ 5417-19-6 ]
[ 51234-09-4 ]
Yield Reaction Conditions Operation in experiment
With chloroform; hexamethylenetetramine beim Erwaermen des Reaktionsprodukts mit wss. Essigsaeure;
4
[ 51234-09-4 ]
[ 109962-81-4 ]
Yield Reaction Conditions Operation in experiment
With hydrogen bromide
5
[ 51234-09-4 ]
[ 5722-94-1 ]
Yield Reaction Conditions Operation in experiment
With potassium permanganate In acetone
6
[ 4885-02-3 ]
[ 4463-33-6 ]
[ 51234-09-4 ]
Yield Reaction Conditions Operation 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;
Reference:
[1]Meier, Herbert; Kretzschmann, Holger; Kolshorn, Heinz
[Journal of Organic Chemistry, 1992, vol. 57, # 25, p. 6847 - 6852]
[2]Sinhababu, Achintya K.; Ghosh, Anil K.; Borchardt, Ronald T.
[Journal of Medicinal Chemistry, 1985, vol. 28, # 9, p. 1273 - 1279]
7
[ 51234-09-4 ]
[ 1100-88-5 ]
[ 144412-67-9 ]
[ 144412-66-8 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation in experiment
88%
With pyridinium chlorochromate In dichloromethane for 1h; Ambient temperature;
10
[ 51234-09-4 ]
[ 80547-78-0 ]
Yield Reaction Conditions Operation in experiment
With lithium aluminium tetrahydride In diethyl ether Ambient temperature;
11
[ 88122-12-7 ]
[ 77-78-1 ]
[ 51234-09-4 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation in experiment
With hydrogenchloride In tetrahydrofuran Heating; Yield given;
Yield Reaction Conditions Operation in experiment
With potassium permanganate; acetone
14
[ 141-82-2 ]
[ 51234-09-4 ]
[ 184850-56-4 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: pyridine; piperidine / 2 h / 100 - 140 °C
2: H2 SO4 / 2 h / Heating
3: 6.22 g / N-bromosuccinimide; benzoyl peroxide / CCl4 / 8 h / Heating
16
[ 51234-09-4 ]
[ 868562-32-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 7 steps
1: pyridine; piperidine / 2 h / 100 - 140 °C
2: H2 SO4 / 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; CH2 Cl2 / 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 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: pyridine; piperidine / 2 h / 100 - 140 °C
2: H2 SO4 / 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 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: pyridine; piperidine / 2 h / 100 - 140 °C
2: H2 SO4 / 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 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: pyridine; piperidine / 2 h / 100 - 140 °C
2: H2 SO4 / 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; CH2 Cl2 / 20 °C / ambient pressure
20
[ 51234-09-4 ]
[ 90266-15-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 8 steps
1: pyridine; piperidine / 2 h / 100 - 140 °C
2: H2 SO4 / 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; CH2 Cl2 / 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: BCl3 *SMe2 / 1,2-dichloro-ethane / 83 °C
2: NaOH / H2 O / 100 °C
23
[ 51234-09-4 ]
(6-Bromo-3,4-dimethoxy-2-methyl-phenyl)-methanol
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: LiAlH4 / diethyl ether / Ambient temperature
2: DMAP, pyridine / CH2 Cl2 / Ambient temperature
3: Br2 / acetic acid / Ambient temperature
4: K2 CO3 / methanol; tetrahydrofuran / Ambient temperature
24
[ 51234-09-4 ]
[ 173040-53-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: LiAlH4 / diethyl ether / Ambient temperature
2: DMAP, pyridine / CH2 Cl2 / Ambient temperature
3: Br2 / acetic acid / Ambient temperature
4: K2 CO3 / methanol; tetrahydrofuran / Ambient temperature
5: Dess-Martin periodinane / CH2 Cl2 / Ambient temperature
25
[ 51234-09-4 ]
Acetic acid 3,4-dimethoxy-2-methyl-benzyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: LiAlH4 / diethyl ether / Ambient temperature
2: DMAP, pyridine / CH2 Cl2 / Ambient temperature
26
[ 51234-09-4 ]
Acetic acid 6-bromo-3,4-dimethoxy-2-methyl-benzyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: LiAlH4 / diethyl ether / Ambient temperature
2: DMAP, pyridine / CH2 Cl2 / 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 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 7 steps
1: LiAlH4 / diethyl ether / Ambient temperature
2: DMAP, pyridine / CH2 Cl2 / Ambient temperature
3: Br2 / acetic acid / Ambient temperature
4: K2 CO3 / methanol; tetrahydrofuran / Ambient temperature
5: Dess-Martin periodinane / CH2 Cl2 / 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, Et3 N / CH2 Cl2 / 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 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: LiAlH4 / diethyl ether / Ambient temperature
2: DMAP, pyridine / CH2 Cl2 / Ambient temperature
3: Br2 / acetic acid / Ambient temperature
4: K2 CO3 / methanol; tetrahydrofuran / Ambient temperature
5: Dess-Martin periodinane / CH2 Cl2 / 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 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 8 steps
1: LiAlH4 / diethyl ether / Ambient temperature
2: DMAP, pyridine / CH2 Cl2 / Ambient temperature
3: Br2 / acetic acid / Ambient temperature
4: K2 CO3 / methanol; tetrahydrofuran / Ambient temperature
5: Dess-Martin periodinane / CH2 Cl2 / 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, Et3 N / CH2 Cl2 / 1 h / -78 deg C up to RT
8: TMSOTf / CH2 Cl2 / 4 h / -78 °C
30
[ 51234-09-4 ]
C21 H26 O4
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 9 steps
1: LiAlH4 / diethyl ether / Ambient temperature
2: DMAP, pyridine / CH2 Cl2 / Ambient temperature
3: Br2 / acetic acid / Ambient temperature
4: K2 CO3 / methanol; tetrahydrofuran / Ambient temperature
5: Dess-Martin periodinane / CH2 Cl2 / 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, Et3 N / CH2 Cl2 / 1 h / -78 deg C up to RT
8: TMSOTf / CH2 Cl2 / 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 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 9 steps
1: LiAlH4 / diethyl ether / Ambient temperature
2: DMAP, pyridine / CH2 Cl2 / Ambient temperature
3: Br2 / acetic acid / Ambient temperature
4: K2 CO3 / methanol; tetrahydrofuran / Ambient temperature
5: Dess-Martin periodinane / CH2 Cl2 / 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, Et3 N / CH2 Cl2 / 1 h / -78 deg C up to RT
8: TMSOTf / CH2 Cl2 / 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 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: BBr3 / CH2 Cl2 / 1.) -78 deg C, 30 min, 2.) 25 deg C, 2 h
2: 76 percent / KI, K2 CO3 / acetone / 7 h / Heating
33
[ 51234-09-4 ]
[ 97102-11-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: BBr3 / CH2 Cl2 / 1.) -78 deg C, 30 min, 2.) 25 deg C, 2 h
2: 76 percent / KI, K2 CO3 / acetone / 7 h / Heating
3: 86 percent / NH4 OAc / 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 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: BBr3 / CH2 Cl2 / 1.) -78 deg C, 30 min, 2.) 25 deg C, 2 h
2: 76 percent / KI, K2 CO3 / acetone / 7 h / Heating
3: 86 percent / NH4 OAc / 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; H2 O / 14 h / 0 - 25 °C
35
[ 51234-09-4 ]
[ 97073-46-6 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: BBr3 / CH2 Cl2 / 1.) -78 deg C, 30 min, 2.) 25 deg C, 2 h
2: 76 percent / KI, K2 CO3 / acetone / 7 h / Heating
3: 86 percent / NH4 OAc / acetic acid / 1.5 h / Heating
36
[ 51234-09-4 ]
[ 97073-49-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: BBr3 / CH2 Cl2 / 1.) -78 deg C, 30 min, 2.) 25 deg C, 2 h
2: 76 percent / KI, K2 CO3 / acetone / 7 h / Heating
3: 86 percent / NH4 OAc / 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 ]
Yield Reaction Conditions Operation 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 / CH2 Cl2 / 1 h / Ambient temperature
38
[ 5417-20-9 ]
[ 51234-09-4 ]
Yield Reaction Conditions Operation 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 / CH2 Cl2 / 1 h / Ambient temperature
39
[ 5722-94-1 ]
[ 51234-09-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 74 percent / LiAlH4 / tetrahydrofuran / 12 h / Heating
2: 88 percent / pyridinium chlorochromate / CH2 Cl2 / 1 h / Ambient temperature
40
[ 51234-09-4 ]
[ 80547-74-6 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: 83 percent / K2 CO3 / 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 / CH2 Cl2 / 1 h / Ambient temperature
44
[ 51234-09-4 ]
[ 102447-10-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: acetic acid; ammonium acetate
2: diethyl ether; LiAlH4
3: Na2 CO3 ; benzene
4: phosphoryl chloride; benzene
45
[ 51234-09-4 ]
1-isopropyl-6,7-dimethoxy-5-methyl-1,2,3,4-tetrahydro-isoquinoline
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: acetic acid; ammonium acetate
2: diethyl ether; LiAlH4
3: Na2 CO3 ; benzene
4: phosphoryl chloride; benzene
5: diethyl ether; lithium alanate
46
[ 51234-09-4 ]
[ 77200-86-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: acetic acid; ammonium acetate
2: diethyl ether; LiAlH4
47
[ 51234-09-4 ]
[ 104216-17-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: aqueous HBr
48
[ 51234-09-4 ]
[ 101108-58-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: acetic acid; ammonium acetate
2: diethyl ether; LiAlH4
3: Na2 CO3 ; benzene
49
[ 51234-09-4 ]
[ 98959-87-6 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: aq. KMnO4 / acetone
2: H2 SO4
51
[ 51234-09-4 ]
[ 15365-27-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: aq. KMnO4 / acetone
2: H2 SO4
3: NBS, (PhCO)2O2 / CCl4
52
[ 51234-09-4 ]
[ 15365-32-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aq. KMnO4 / acetone
2: H2 SO4
3: NBS, (PhCO)2O2 / CCl4
4: Et3 N / diethyl ether
53
[ 74866-17-4 ]
[ 68-12-2 ]
[ 51234-09-4 ]
54
[ 51234-09-4 ]
[ 106-65-0 ]
[ 1160440-49-2 ]
Yield Reaction Conditions Operation 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
C10 H11 ClO3
[ No CAS ]
[ 51234-09-4 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation in experiment
65%
Stage #1: 2-methyl-3,4-dimethoxybenzoic acid With lithium aluminium tetrahydride In tetrahydrofuran
Stage #2: With pyridinium chlorochromate
Reference:
[1]Le, Tin Thanh; Chau, Nguyet Trang Thanh; Nguyen, Tai Tan; Brien, Josselin; Thai, Trieu Tien; Nourry, Arnaud; Castanet, Anne-Sophie; Nguyen, Kim Phi Phung; Mortier, Jacques
[Journal of Organic Chemistry, 2011, vol. 76, # 2, p. 601 - 608]
57
[ 51234-09-4 ]
[ 1261383-34-9 ]
Yield Reaction Conditions Operation 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
Reference:
[1]Le, Tin Thanh; Chau, Nguyet Trang Thanh; Nguyen, Tai Tan; Brien, Josselin; Thai, Trieu Tien; Nourry, Arnaud; Castanet, Anne-Sophie; Nguyen, Kim Phi Phung; Mortier, Jacques
[Journal of Organic Chemistry, 2011, vol. 76, # 2, p. 601 - 608]
58
[ 51234-09-4 ]
[ 1261383-36-1 ]
Yield Reaction Conditions Operation 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
Reference:
[1]Le, Tin Thanh; Chau, Nguyet Trang Thanh; Nguyen, Tai Tan; Brien, Josselin; Thai, Trieu Tien; Nourry, Arnaud; Castanet, Anne-Sophie; Nguyen, Kim Phi Phung; Mortier, Jacques
[Journal of Organic Chemistry, 2011, vol. 76, # 2, p. 601 - 608]
59
[ 51234-09-4 ]
[ 1160440-66-3 ]
Yield Reaction Conditions Operation 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
Reference:
[1]Le, Tin Thanh; Chau, Nguyet Trang Thanh; Nguyen, Tai Tan; Brien, Josselin; Thai, Trieu Tien; Nourry, Arnaud; Castanet, Anne-Sophie; Nguyen, Kim Phi Phung; Mortier, Jacques
[Journal of Organic Chemistry, 2011, vol. 76, # 2, p. 601 - 608]