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Chemical Structure| 20469-61-8
Chemical Structure| 20469-61-8
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Product Details of [ 20469-61-8 ]

CAS No. :20469-61-8 MDL No. :MFCD00142783
Formula : C10H14O Boiling Point : -
Linear Structure Formula :- InChI Key :AWONIZVBKXHWJP-UHFFFAOYSA-N
M.W : 150.22 Pubchem ID :88555
Synonyms :

Calculated chemistry of [ 20469-61-8 ]

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 : 9.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.61
Log Po/w (XLOGP3) : 2.99
Log Po/w (WLOGP) : 2.62
Log Po/w (MLOGP) : 2.76
Log Po/w (SILICOS-IT) : 3.24
Consensus Log Po/w : 2.84

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.99
Solubility : 0.153 mg/ml ; 0.00102 mol/l
Class : Soluble
Log S (Ali) : -2.85
Solubility : 0.213 mg/ml ; 0.00142 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.67
Solubility : 0.0323 mg/ml ; 0.000215 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 20469-61-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

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.

  • Upstream synthesis route of [ 20469-61-8 ]
  • Downstream synthetic route of [ 20469-61-8 ]

[ 20469-61-8 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 697-82-5 ]
  • [ 74-88-4 ]
  • [ 20469-61-8 ]
Reference: [1] Chemical & Pharmaceutical Bulletin, 1981, vol. 29, # 10, p. 2825 - 2831
[2] Russian Journal of Organic Chemistry, 1993, vol. 29, # 4, p. 572 - 575[3] Zhurnal Organicheskoi Khimii, 1993, vol. 29, # 4, p. 682 - 686
[4] Tetrahedron Letters, 2007, vol. 48, # 8, p. 1337 - 1340
[5] Chemistry - A European Journal, 2014, vol. 20, # 29, p. 8904 - 8908
[6] Helvetica Chimica Acta, 2002, vol. 85, # 9, p. 2926 - 2929
[7] Pharmaceutical Chemistry Journal, 1994, vol. 28, # 5, p. 343 - 348[8] Khimiko-Farmatsevticheskii Zhurnal, 1994, vol. 28, # 5, p. 43 - 47
[9] Pharmaceutical Research, 1995, vol. 12, # 7, p. 983 - 992
[10] Patent: US4368150, 1983, A,
[11] Patent: US4476051, 1984, A,
[12] Phosphorus, Sulfur and Silicon and the Related Elements, 2010, vol. 185, # 3, p. 501 - 508
[13] Bioorganic Chemistry, 2018, vol. 80, p. 253 - 260
  • 2
  • [ 697-82-5 ]
  • [ 616-38-6 ]
  • [ 20469-61-8 ]
YieldReaction ConditionsOperation in experiment
99% at 180℃; for 1 h; General procedure: General procedure for the alkylation of phenols with dimethyl carbonate. A 17-mL stainless steel high-pressure micro reactor was charged with 3 mmol of Mn2(CO)10, W(CO)6, or Co2(CO)8, 100 mmol of the corresponding phenol, and 300 mmol of dimethyl carbonate, and the reactor was hermetically closed and heated for 1 h at 180°C. The reactor was then cooled to room temperature and opened, and the mixture was filtered through a layer of alumina. Unreacted dimethyl carbonate was distilled off, and the residue was distilled under atmospheric or reduced pressure or recrystallized from ethanol. 1-Methoxy-2,3,5-trimethylbenzene. Yield 99percent, bp 84.5–85°C (7 mm). 13C NMR spectrum, δC, ppm: 11.60, 20.03, 21.38 (CH3); 110.52 (C6), 119.95 (C2), 124.92 (C4), 137.32 (C3), 137.54 (C5), 157.43 (C1). Found, percent: C 79.87; H 9.35. C10H14O. Calculated, percent: C 79.96; H 9.39.
Reference: [1] Russian Journal of Organic Chemistry, 2015, vol. 51, # 3, p. 330 - 334[2] Methylation of Phenol and Its Derivatives with Dimethyl Carbonate in the Presence of Mn2(CO)10, W(CO)6, and Co2(CO)8, 2015, vol. 51, # 3, p. 330 - 334,5
  • 3
  • [ 5469-19-2 ]
  • [ 20469-61-8 ]
Reference: [1] Russian Journal of Organic Chemistry, 1993, vol. 29, # 4, p. 572 - 575[2] Zhurnal Organicheskoi Khimii, 1993, vol. 29, # 4, p. 682 - 686
  • 4
  • [ 154152-57-5 ]
  • [ 20469-61-8 ]
Reference: [1] Russian Journal of Organic Chemistry, 1993, vol. 29, # 4, p. 572 - 575[2] Zhurnal Organicheskoi Khimii, 1993, vol. 29, # 4, p. 682 - 686
  • 5
  • [ 697-82-5 ]
  • [ 77-78-1 ]
  • [ 20469-61-8 ]
Reference: [1] Liebigs Annalen der Chemie, 1984, vol. 1984, # 10, p. 1740 - 1745
[2] Chemische Berichte, 1915, vol. 48, p. 1713
  • 6
  • [ 767-77-1 ]
  • [ 20469-61-8 ]
Reference: [1] Russian Journal of Organic Chemistry, 1993, vol. 29, # 4, p. 572 - 575[2] Zhurnal Organicheskoi Khimii, 1993, vol. 29, # 4, p. 682 - 686
  • 7
  • [ 95-63-6 ]
  • [ 64-19-7 ]
  • [ 935-92-2 ]
  • [ 527-17-3 ]
  • [ 20469-61-8 ]
  • [ 62687-45-0 ]
  • [ 21573-38-6 ]
  • [ 109576-73-0 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 11, p. 2071 - 2078[2] Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 11, p. 2306 - 2315
  • 8
  • [ 697-82-5 ]
  • [ 64-19-7 ]
  • [ 935-92-2 ]
  • [ 13038-87-4 ]
  • [ 20469-61-8 ]
  • [ 34649-27-9 ]
  • [ 109576-73-0 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 11, p. 2071 - 2078[2] Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 11, p. 2306 - 2315
  • 9
  • [ 79-21-0 ]
  • [ 697-82-5 ]
  • [ 935-92-2 ]
  • [ 700-13-0 ]
  • [ 13038-87-4 ]
  • [ 20469-61-8 ]
  • [ 34649-27-9 ]
Reference: [1] J. Gen. Chem. USSR (Engl. Transl.), 1987, vol. 57, # 4, p. 819 - 826[2] Zhurnal Obshchei Khimii, 1987, vol. 57, # 4, p. 923 - 930
  • 10
  • [ 20469-61-8 ]
  • [ 68-12-2 ]
  • [ 54344-92-2 ]
Reference: [1] Russian Journal of Organic Chemistry, 1993, vol. 29, # 4, p. 572 - 575[2] Zhurnal Organicheskoi Khimii, 1993, vol. 29, # 4, p. 682 - 686
[3] Helvetica Chimica Acta, 2002, vol. 85, # 9, p. 2926 - 2929
[4] Chemistry - A European Journal, 2014, vol. 20, # 29, p. 8904 - 8908
[5] Liebigs Annalen der Chemie, 1984, vol. 1984, # 10, p. 1740 - 1745
[6] Pharmaceutical Chemistry Journal, 1994, vol. 28, # 5, p. 343 - 348[7] Khimiko-Farmatsevticheskii Zhurnal, 1994, vol. 28, # 5, p. 43 - 47
[8] Phosphorus, Sulfur and Silicon and the Related Elements, 2010, vol. 185, # 3, p. 501 - 508
[9] Bioorganic Chemistry, 2018, vol. 80, p. 253 - 260
  • 11
  • [ 20469-61-8 ]
  • [ 697-82-5 ]
  • [ 74-88-4 ]
  • [ 54344-92-2 ]
Reference: [1] Patent: US4021574, 1977, A,
  • 12
  • [ 4885-02-3 ]
  • [ 20469-61-8 ]
  • [ 54344-92-2 ]
Reference: [1] Pharmaceutical Research, 1995, vol. 12, # 7, p. 983 - 992
  • 13
  • [ 20469-61-8 ]
  • [ 69877-38-9 ]
Reference: [1] Pharmaceutical Research, 1995, vol. 12, # 7, p. 983 - 992
[2] Russian Journal of Organic Chemistry, 1993, vol. 29, # 4, p. 572 - 575[3] Zhurnal Organicheskoi Khimii, 1993, vol. 29, # 4, p. 682 - 686
[4] Chemistry - A European Journal, 2014, vol. 20, # 29, p. 8904 - 8908
  • 14
  • [ 20469-61-8 ]
  • [ 80745-07-9 ]
YieldReaction ConditionsOperation in experiment
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 2,3,5-trimethylanisole, 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-5percent 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 (67.0percent), 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.
67.0% With chlorosulfonic acid In dichloromethane (2)
Synthesis of 4-methoxy-2,3,6-trimethylbenzenesulfonyl chloride
In 500 ml of methylene chloride was dissolved 4.5 g of 2,3,5-trimethylanisole 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--5percent 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 (67.0percent).
m.p. 56°-58° C.
Reference: [1] Chemical & Pharmaceutical Bulletin, 1981, vol. 29, # 10, p. 2825 - 2831
[2] Tetrahedron Letters, 2007, vol. 48, # 8, p. 1337 - 1340
[3] Patent: US4368150, 1983, A,
[4] Patent: US4476051, 1984, A,
  • 15
  • [ 20469-61-8 ]
  • [ 80745-10-4 ]
Reference: [1] Chemical & Pharmaceutical Bulletin, 1981, vol. 29, # 10, p. 2825 - 2831
  • 16
  • [ 20469-61-8 ]
  • [ 80745-09-1 ]
Reference: [1] Chemical & Pharmaceutical Bulletin, 1981, vol. 29, # 10, p. 2825 - 2831
  • 17
  • [ 20469-61-8 ]
  • [ 54757-47-0 ]
Reference: [1] Pharmaceutical Research, 1995, vol. 12, # 7, p. 983 - 992
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