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Quality Control of [ 20469-61-8 ] Purity: 95% SDS Specification

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Product Details of [ 20469-61-8 ]

CAS No. :	20469-61-8
Formula :	C₁₀H₁₄O
M.W :	150.22
SMILES Code :	CC1=CC(C)=C(C)C(OC)=C1
MDL No. :	MFCD00142783
InChI Key :	AWONIZVBKXHWJP-UHFFFAOYSA-N
Pubchem ID :	88555

Safety of [ 20469-61-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 20469-61-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.4
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	47.83
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	9.23 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.61
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.99
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.62
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.76
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.24
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.84

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.99
Solubility	0.153 mg/ml ; 0.00102 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.85
Solubility	0.213 mg/ml ; 0.00142 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.67
Solubility	0.0323 mg/ml ; 0.000215 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.09 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.0

Application In Synthesis of [ 20469-61-8 ]

* 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 [ 20469-61-8 ]

[ 20469-61-8 ] Synthesis Path-Downstream 1~33

1
[ 14368-49-1 ]
[ 20469-61-8 ]
(4-methoxy-2,3,6-trimethyl-phenyl)-(4-nitro-phenyl)-diazene [ No CAS ]

References: [1]Chemische Berichte,1915,vol. 48,p. 1713.

2
[ 20469-61-8 ]
[ 122567-24-2 ]

References: [1]Chemische Berichte,1940,vol. 73,p. 995,999.
[2]Journal of Organic Chemistry,1989,vol. <17> 54,p. 4034 - 4038.

3
[ 697-82-5 ]
[ 77-78-1 ]
[ 20469-61-8 ]

References: [1]Liebigs Annalen der Chemie,1984,vol. 1984,p. 1740 - 1745.
[2]Chemische Berichte,1915,vol. 48,p. 1713.

4
[ 20469-61-8 ]
[ 52060-73-8 ]

References: [1]Journal of the Chemical Society,1962,p. 3751 - 3758.
[2]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 3601 - 3611.

5
[ 20469-61-8 ]
1-Methoxy-2,3,5-trimethyl-cyclohexa-1,4-diene [ No CAS ]

References: [1]Roczniki Chemii,1974,vol. 48,p. 1951 - 1963.

6
[ 20469-61-8 ]
[ 16782-79-9 ]

References: [1]Roczniki Chemii,1974,vol. 48,p. 1951 - 1963.

7
[ 20469-61-8 ]
[ 39849-85-9 ]
[ 52928-08-2 ]

Yield	Reaction Conditions	Operation in experiment
30%	With hydrogenchloride;aluminium trichloride; In dichloromethane;	EXAMPLE 1 2-(4-Methoxy-2,3,6-trimethylbenzoyl)-5-nitrothiazole One gram of 5-nitrothiazole-2-carboxylic acid chloride in 10 ml. of methylene chloride is combined with 850 mg. of <strong>[20469-61-8]<strong>[20469-61-8]2,3,5-trimethylanisol</strong>e</strong> and then with 1.6 g. of aluminum chloride. After three hours of agitation at room temperature, the reaction mixture is poured on 50 ml. of 1N HCl and extracted with ethyl acetate. After drying of the solution and evaporating the solvent under vacuum, the crystalline residue is recrystallized from methanol/chloroform. Yield: 30%; m.p. 125-126 C.

References: [1]Patent: US4006241,1977,A .
[2]European Journal of Medicinal Chemistry,1974,vol. 9,p. 35 - 40.

8
[ 79-21-0 ]
[ 697-82-5 ]
[ 935-92-2 ]
[ 700-13-0 ]
[ 13038-87-4 ]
[ 20469-61-8 ]
[ 34649-27-9 ]
5-acetoxy-2,4-dihydroxy-2,4,5-trimethyl-3,6-lacto-1-hexanoic acid [ No CAS ]

References: [1]Journal of general chemistry of the USSR,1987,vol. 57,p. 819 - 826.
Zhurnal Obshchei Khimii,1987,vol. 57,p. 923 - 930.

9
[ 625-35-4 ]
[ 20469-61-8 ]
[ 122567-30-0 ]

References: [1]Journal of Organic Chemistry,1989,vol. <17> 54,p. 4034 - 4038.

10
[ 3230-69-1 ]
[ 20469-61-8 ]
[ 124743-94-8 ]
3-Methoxy-1,2,5-trimethyl-4-((E)-3-methyl-pent-2-en-4-ynyl)-benzene [ No CAS ]

References: [1]Helvetica Chimica Acta,1989,vol. 72,p. 370 - 376.
[2]Helvetica Chimica Acta,1989,vol. 72,p. 370 - 376.

11
[ 20469-61-8 ]
[ 62012-53-7 ]

References: [1]Journal of the American Chemical Society,1980,vol. 102,p. 6504 - 6512.
[2]Journal of Organic Chemistry,1977,vol. 42,p. 764 - 765.

12
[ 20469-61-8 ]
[ 80745-07-9 ]

Yield	Reaction Conditions	Operation in experiment
5.0 g (67.0%)	With chlorosulfonic acid; In dichloromethane;	(2) Synthesis of 4-methoxy-2,3,6-trimethylbenzensulfonyl chloride In 500 ml of methylenchloride was dissolved 4.5 g of <strong>[20469-61-8]<strong>[20469-61-8]2,3,5-trimethylanisol</strong>e</strong>, and after cooling at -5~-10 C., a solution (400 ml) of 6.0 ml of chlorosulfonic acid in methylene chloride was added dropwise to the mixture. The reaction mixture was kept at room temperature and then poured into ice-5% aqueous NaHCO3. The methylene chloride layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was crystallized from n-hexane and filtered. Yield 5.0 g (67.0%), m.p. 56-58 C. Elemental analysis for C10 H13 O3 SCl; Calcd.: C, 48.29; H, 5.27; S, 12.89; Cl 14.26; Found: C, 48.42; H, 5.21; S, 12.61; Cl 14.25.
5.0 g (67.0%)	With chlorosulfonic acid; In dichloromethane;	(2) Synthesis of <strong>[20469-61-8]4-methoxy-2,3,6-trimethylbenzene</strong>sulfonyl chloride In 500 ml of methylene chloride was dissolved 4.5 g of <strong>[20469-61-8]<strong>[20469-61-8]2,3,5-trimethylanisol</strong>e</strong> and the solution was cooled to -5 C. to -10 C. A solution of 6.0 ml of chlorosulfonic acid in 400 ml of methylene chloride was added dropwise, and then the temperature was allowed to rise to room temperature. The mixture was poured into an ice--5% aqueous sodium hydrogen carbonate mixture. The methylene chloride layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off, and the residue was crystallized from n-hexane. Yield 5.0 g (67.0%). m.p. 56-58 C.

References: [1]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 2825 - 2831.
[2]Tetrahedron Letters,2007,vol. 48,p. 1337 - 1340.
[3]Patent: US4368150,1983,A .
[4]Patent: US4476051,1984,A .

13
[ 20469-61-8 ]
[ 84244-55-3 ]

References: [1]Helvetica Chimica Acta,1989,vol. 72,p. 370 - 376.
[2]Journal of Organic Chemistry,1994,vol. 59,p. 4473 - 4481.

14
[ 95-63-6 ]
[ 64-19-7 ]
[ 935-92-2 ]
[ 527-17-3 ]
[ 20469-61-8 ]
[ 62687-45-0 ]
[ 21573-38-6 ]
[ 109576-73-0 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1986,vol. 22,p. 2071 - 2078.
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 2306 - 2315.

15
[ 697-82-5 ]
[ 64-19-7 ]
[ 935-92-2 ]
[ 13038-87-4 ]
[ 20469-61-8 ]
[ 34649-27-9 ]
1-acetoxy-4-methoxy-2,3,5-trimethylbenzene [ No CAS ]
[ 109576-73-0 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1986,vol. 22,p. 2071 - 2078.
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 2306 - 2315.

16
[ 20469-61-8 ]
[ 68-12-2 ]
[ 54344-92-2 ]

References: [1]Russian Journal of Organic Chemistry,1993,vol. 29,p. 572 - 575.
Zhurnal Organicheskoi Khimii,1993,vol. 29,p. 682 - 686.
[2]Helvetica Chimica Acta,2002,vol. 85,p. 2926 - 2929.
[3]Chemistry - A European Journal,2014,vol. 20,p. 8904 - 8908.
[4]Liebigs Annalen der Chemie,1984,vol. 1984,p. 1740 - 1745.
[5]Pharmaceutical Chemistry Journal,1994,vol. 28,p. 343 - 348.
Khimiko-Farmatsevticheskii Zhurnal,1994,vol. 28,p. 43 - 47.
[6]Phosphorus, Sulfur and Silicon and the Related Elements,2010,vol. 185,p. 501 - 508.
[7]Bioorganic Chemistry,2018,vol. 80,p. 253 - 260.

17
[ 20469-61-8 ]
[ 102-92-1 ]
[ 113450-91-2 ]

References: [1]Journal of Organic Chemistry,1989,vol. <17> 54,p. 4034 - 4038.

18
[ 20469-61-8 ]
[ 814-68-6 ]
[ 113450-86-5 ]

References: [1]Journal of Organic Chemistry,1989,vol. <17> 54,p. 4034 - 4038.

19
[ 697-82-5 ]
[ 74-88-4 ]
[ 20469-61-8 ]

Yield	Reaction Conditions	Operation in experiment
48%		General procedure: To a solution of the respective phenol derivative (23f-k, 15.0 mg, 0.11 mmol, 1 equiv) in dry DMF (2.2 mL), K2CO3 (15.2 mg, 0.11 mmol, 1 equiv) was added and the mixture was stirred at room temperature for 30 min. Methyl iodide (31 mg, 0.22 mmol, 2 equiv) was added and the reaction mixture was stirred at room temperature overnight. The reaction was quenched by addition of water and the aqueous phase was extracted three times with EtOAc. The combined organic layers were dried over MgSO4 and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel (cyclohexane/ethyl acetate 20:1).The pure products were obtained as pale yellow liquids.
	In water; dimethyl sulfoxide;	(1) Synthesis of 2,3,5-trimethylanisole In 100 ml of DMSO were dissolved 10 g of 2,3,5-trimethylphenol and 10.4 ml of methyl iodide. Under ice-cooling, 5.6 g of 60% sodium hydride in oil was added, and the mixture was stirred at room temperature for 10 hours. After addition of water, the extraction with ether was carried out. The ether layer was washed with water and dried over anhydrous sodium sulfate. Removal of the solvent by distillation leaves the oily substance. Yield 12.9 g (quantitative)
	In water; dimethyl sulfoxide;	(1) Synthesis of 2,3,5-trimethylanisole In 100 ml of dimethyl sulfoxide were dissolved 10 g of 2,3,5-trimethylphenol and 10.4 ml of methyl iodide and the solution was ice-cooled. To this solution was added 5.6 g of 60% oily sodium hydride and the mixture was stirred for 10 hours. Water was added and the resulting mixture was extracted with ether. The ether layer was washed with water and dried over anhydrous sodium sulfate. The solvent was then distilled off to give an oily substance. Yield 12.9 g (quantitative).

References: [1]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 2825 - 2831.
[2]Russian Journal of Organic Chemistry,1993,vol. 29,p. 572 - 575.
Zhurnal Organicheskoi Khimii,1993,vol. 29,p. 682 - 686.
[3]Tetrahedron Letters,2007,vol. 48,p. 1337 - 1340.
[4]Chemistry - A European Journal,2014,vol. 20,p. 8904 - 8908.
[5]Helvetica Chimica Acta,2002,vol. 85,p. 2926 - 2929.
[6]Pharmaceutical Chemistry Journal,1994,vol. 28,p. 343 - 348.
Khimiko-Farmatsevticheskii Zhurnal,1994,vol. 28,p. 43 - 47.
[7]Pharmaceutical Research,1995,vol. 12,p. 983 - 992.
[8]Beilstein Journal of Organic Chemistry,2018,vol. 14,p. 2974 - 2990.
[9]Patent: US4368150,1983,A .
[10]Patent: US4476051,1984,A .
[11]Phosphorus, Sulfur and Silicon and the Related Elements,2010,vol. 185,p. 501 - 508.
[12]Bioorganic Chemistry,2018,vol. 80,p. 253 - 260.

20
[ 4885-02-3 ]
[ 20469-61-8 ]
[ 54344-92-2 ]

References: [1]Pharmaceutical Research,1995,vol. 12,p. 983 - 992.

23
[ 20469-61-8 ]
[ 7697-37-2 ]
[ 64-19-7 ]
[ 122567-24-2 ]

References: [1]Chemische Berichte,1940,vol. 73,p. 995,999.

24
[ 20469-61-8 ]
[ 62012-53-7 ]
3-chloro-4,4'-dimethoxy-2,2',3'5,6,6'-hexamethylbiphenyl [ No CAS ]

References: [1]Synlett,2004,p. 1970 - 1974.

25
[ 20469-61-8 ]
N-(1-cyano-3-methyl-butyl)-4-methoxy-2,3,6-trimethyl-benzenesulfonamide [ No CAS ]