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Chemical Structure| 808-57-1 Chemical Structure| 808-57-1
Chemical Structure| 808-57-1

2,3,6,7,10,11-Hexamethoxytriphenylene

CAS No.: 808-57-1

4.5 *For Research Use Only !

Cat. No.: A205066 Purity: 97%

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Product Details of [ 808-57-1 ]

CAS No. :808-57-1
Formula : C24H24O6
M.W : 408.44
SMILES Code : COC1=C(OC)C=C2C3=CC(OC)=C(OC)C=C3C4=CC(OC)=C(OC)C=C4C2=C1
MDL No. :MFCD00075571
InChI Key :TXROZCSFVVIBFI-UHFFFAOYSA-N
Pubchem ID :4607363

Safety of [ 808-57-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Calculated chemistry of [ 808-57-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 30
Num. arom. heavy atoms 18
Fraction Csp3 0.25
Num. rotatable bonds 6
Num. H-bond acceptors 6.0
Num. H-bond donors 0.0
Molar Refractivity 117.91
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

55.38 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

4.07
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

4.71
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

5.2
Log Po/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.

2.62
Log Po/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

5.32
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.38

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-5.39
Solubility 0.00167 mg/ml ; 0.0000041 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-5.6
Solubility 0.00102 mg/ml ; 0.0000025 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately 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

-8.11
Solubility 0.00000321 mg/ml ; 0.0000000079 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly 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

No
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

Yes
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

Yes
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

Yes
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.

-5.45 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

0.0
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

1.0 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<2.0
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)

2.24

Application In Synthesis of [ 808-57-1 ]

* 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 [ 808-57-1 ]
  • Downstream synthetic route of [ 808-57-1 ]

[ 808-57-1 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 91-16-7 ]
  • [ 808-57-1 ]
YieldReaction ConditionsOperation in experiment
90.1% at 25℃; for 24 h; A type B crystal of 2,3,6,7,10,11-hexahydroxytriphenylene monohydrate was synthesized according to the process described in Synthesis, 477, 1994 and JP-A-8-119894. Namely, 1,2-dimethoxybenzene (31.78 g, 0.23 moles) and anhydrous ferric chloride (120 g, 0.74 moles) were dissolved in 70percent sulfuric acid, and the solution was reacted at 25°C for 24 hours with stirring. After completion of the reaction, the solution was poured into ice water (500 g), and the precipitated crystal was collected by filtration. After the resultant crystal was washed with water (1 L), and then dried to give pale purple colored 2,3,6,7,10,11-hexamethoxytriphenylene (28.2 g, theoretical yield from 1,2-dimethoxybenzene: 90.1percent) (the method of Synthesis, 477, 1994).
85.4% at 10 - 15℃; for 6 h; 600 ml of ethyl acetate was added into a 1000ml four-necked flask, sodium peroxydisulfate 102.4g (0.43 mol) and o-xylene 45.7 g (0.43 mol) were added, stirred and cooled at internal temperature of 10 degrees C. Anhydrous iron(III) chloride 345.4g (2.10 mol) was added little by little, reacted at an internal temperature of 10-15 degrees C for 6 hours. After completion of the reaction, reaction mixture was cooled, 2000 ml of water was added and stirred for 10minutes. The aqueous layer of the solution was separated, and the organic layer was washed with 800 ml of salt solution. 600 ml of methanol was added to the organic layer and crystallized at 15-25 degrees C for 1 hour, the crystals were filtered, and dried to obtain 19.5 g (43.6percent of yield) of objects as gray crystal.
82% With trifluorormethanesulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 20℃; for 10 h; Inert atmosphere General procedure: An oven-dried 20 mL scintillation vial, equipped with a magnetic stir-bar, was charged with the starting material (1.0 equiv), DDQ (1.0 equiv), trifluoromethanesulfonic acid (1.4percent v/v, 3.0 equiv), and 1,2-dichloroethane (0.05 M). The reaction mixture was then allowed to stir at ambient temperature for 10 h. After this time, methanol (0.05M) was added, and the solution was then allowed to stir at ambient temperature for an additional hour. Upon addition of the methanol, some solids precipitated out of the solution. Then, the solvent was removed from the heterogeneous mixture under reduced pressure. The crude material was purified by either recrystallization (methanol/DCM) or silica-gel column chromatography (hexanes/DCM) to give the title compounds.
80% With iron(III) chloride; sulfuric acid In dichloromethane at 20℃; for 3 h; A solution of 1,2-dimethoxybenzene (10 g, 72.4 mmol) in dichloromethane(50 ml) was added dropwise to a suspension of anhydrous FeCl3 (35.22 g, 217.2 mmol) in dichloromethane (100 ml) and concentrated sulphuric acid (0.5 ml). After complete addition (15 min), the reaction mixture was further stirred for 3 h at room temperature. 200 ml of methanol were then slowly added under vigorous stirring. The obtained mixture was further stirred for additional 30 min. And the precipitate was filtered off, washed with methanol (5 × 100 ml) and dried under reduced pressure to give a purple solid. Yield: 80percent, 1HNMR (CDCl3) δ/ppm: 4.10 (s, 18H, OCH3), 7.80 (s, 6H, ArH).

References: [1] Angewandte Chemie - International Edition, 2010, vol. 49, # 44, p. 8209 - 8213.
[2] Synthesis, 1994, vol. 1, # 5, p. 477 - 478.
[3] Patent: EP2177495, 2010, A1, . Location in patent: Page/Page column 12.
[4] Synthetic Communications, 1999, vol. 29, # 10, p. 1767 - 1771.
[5] Journal of the American Chemical Society, 2017, vol. 139, # 46, p. 16759 - 16767.
[6] Patent: JP5731346, 2015, B2, . Location in patent: Paragraph 0086; 0087; 0095.
[7] Journal of Materials Chemistry, 2002, vol. 12, # 8, p. 2208 - 2213.
[8] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3458 - 3462.
[9] Journal of Molecular Liquids, 2016, vol. 223, p. 734 - 740.
[10] Journal of the American Chemical Society, 2009, vol. 131, p. 7662 - 7677.
[11] Chemical Communications, 1997, # 17, p. 1615 - 1616.
[12] Journal of the American Chemical Society, 1980, vol. 102, # 21, p. 6504 - 6512.
[13] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1975, p. 2185 - 2189.
[14] Tetrahedron, 1965, vol. 21, p. 3229 - 3236.
[15] Tetrahedron, 1991, vol. 47, # 4/5, p. 791 - 798.
[16] Molecular Crystals and Liquid Crystals (1969-1991), 1985, vol. 125, p. 279 - 288.
[17] Journal of Structural Chemistry, 2001, vol. 42, # 1, p. 38 - 42.
[18] Chemistry Letters, 1994, # 6, p. 981 - 984.
[19] Journal of Physical Chemistry, 1995, vol. 99, # 3, p. 1005 - 1017.
[20] Synthesis, 1997, # 11, p. 1285 - 1290.
[21] Russian Chemical Bulletin, 2004, vol. 53, # 8, p. 1743 - 1748.
[22] Chemical Communications, 2015, vol. 51, # 21, p. 4368 - 4371.
[23] Chimia, 2015, vol. 69, # 9, p. 520 - 523.
[24] Patent: JP2017/31106, 2017, A, . Location in patent: Paragraph 0052-0055.
[25] Journal of Materials Chemistry A, 2017, vol. 5, # 24, p. 12080 - 12085.
  • 2
  • [ 1595078-14-0 ]
  • [ 808-57-1 ]
References: [1] Organic Letters, 2014, vol. 16, # 9, p. 2338 - 2341.
  • 3
  • [ 2319-91-7 ]
  • [ 808-57-1 ]
References: [1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 19, p. 3057 - 3061.
  • 4
  • [ 5460-32-2 ]
  • [ 808-57-1 ]
References: [1] Journal of the American Chemical Society, 1980, vol. 102, # 21, p. 6504 - 6512.
  • 5
  • [ 91-16-7 ]
  • [ 1004-66-6 ]
  • [ 808-57-1 ]
  • [ 47075-39-8 ]
References: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1982, vol. 36, # 5, p. 317 - 326.
  • 6
  • [ 91-16-7 ]
  • [ 808-57-1 ]
  • [ 152634-10-1 ]
References: [1] Journal of the Chemical Society, Chemical Communications, 1994, # 4, p. 465 - 466.
  • 7
  • [ 91-16-7 ]
  • [ 1004-66-6 ]
  • [ 808-57-1 ]
References: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1982, vol. 36, # 5, p. 317 - 326.
  • 8
  • [ 91-16-7 ]
  • [ 161691-13-0 ]
  • [ 808-57-1 ]
  • [ 152634-10-1 ]
References: [1] Journal of the Chemical Society, Chemical Communications, 1994, # 4, p. 465 - 466.
  • 9
  • [ 89978-46-1 ]
  • [ 808-57-1 ]
References: [1] Organic Letters, 2014, vol. 16, # 9, p. 2338 - 2341.
  • 10
  • [ 91-16-7 ]
  • [ 1004-66-6 ]
  • [ 808-57-1 ]
  • [ 47075-39-8 ]
References: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1982, vol. 36, # 5, p. 317 - 326.
  • 11
  • [ 91-16-7 ]
  • [ 808-57-1 ]
  • [ 139021-90-2 ]
References: [1] Tetrahedron Letters, 1991, vol. 32, # 50, p. 7405 - 7408.
  • 12
  • [ 37895-73-1 ]
  • [ 808-57-1 ]
References: [1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 19, p. 3057 - 3061.
  • 13
  • [ 91-16-7 ]
  • [ 14098-44-3 ]
  • [ 808-57-1 ]
  • [ 139021-90-2 ]
References: [1] Tetrahedron Letters, 1991, vol. 32, # 50, p. 7405 - 7408.
  • 14
  • [ 91-16-7 ]
  • [ 14098-24-9 ]
  • [ 808-57-1 ]
  • [ 139021-91-3 ]
References: [1] Tetrahedron Letters, 1991, vol. 32, # 50, p. 7405 - 7408.
  • 15
  • [ 91-16-7 ]
  • [ 67950-78-1 ]
  • [ 808-57-1 ]
  • [ 139021-92-4 ]
References: [1] Tetrahedron Letters, 1991, vol. 32, # 50, p. 7405 - 7408.
  • 16
  • [ 274-09-9 ]
  • [ 91-16-7 ]
  • [ 808-57-1 ]
  • [ 134025-14-2 ]
  • [ 134025-19-7 ]
References: [1] Tetrahedron, 1991, vol. 47, # 4/5, p. 791 - 798.
  • 17
  • [ 91-16-7 ]
  • [ 4218-87-5 ]
  • [ 808-57-1 ]
  • [ 134025-12-0 ]
  • [ 134025-17-5 ]
  • [ 134025-07-3 ]
References: [1] Tetrahedron, 1991, vol. 47, # 4/5, p. 791 - 798.
  • 18
  • [ 493-09-4 ]
  • [ 91-16-7 ]
  • [ 808-57-1 ]
  • [ 134025-10-8 ]
  • [ 134025-15-3 ]
  • [ 134025-08-4 ]
References: [1] Tetrahedron, 1991, vol. 47, # 4/5, p. 791 - 798.
[2] Tetrahedron, 1991, vol. 47, # 4/5, p. 791 - 798.
 

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