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Chemical Structure| 6342-80-9 Chemical Structure| 6342-80-9

Structure of 6342-80-9

Chemical Structure| 6342-80-9

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Product Details of [ 6342-80-9 ]

CAS No. :6342-80-9
Formula : C11H12O3
M.W : 192.21
SMILES Code : O=C1CCC2=C1C=CC(OC)=C2OC
MDL No. :MFCD00463187
InChI Key :XQODIRIVQXQUFN-UHFFFAOYSA-N
Pubchem ID :240446

Safety of [ 6342-80-9 ]

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

Computational Chemistry of [ 6342-80-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 6
Fraction Csp3 0.36
Num. rotatable bonds 2
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 52.47
TPSA ?

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

35.53 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.16
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

1.61
Log Po/w (WLOGP)?

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

1.83
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.

1.03
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

2.73
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.87

Water Solubility

Log S (ESOL):?

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

-2.23
Solubility 1.13 mg/ml ; 0.00587 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.

-1.97
Solubility 2.07 mg/ml ; 0.0108 mol/l
Class?

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

Very 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

-3.37
Solubility 0.0812 mg/ml ; 0.000423 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.

-6.33 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

1.0
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)

1.97

Application In Synthesis of [ 6342-80-9 ]

* 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 [ 6342-80-9 ]

[ 6342-80-9 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 6342-80-9 ]
  • [ 535-11-5 ]
  • 2-(6,7-dimethoxy-inden-3-yl)-propionic acid ethyl ester [ No CAS ]
  • 2
  • [ 10538-48-4 ]
  • [ 6342-80-9 ]
YieldReaction ConditionsOperation in experiment
44% With Eaton?s reagent; at 20℃; for 72h; Carboxylic acid 9 (4.99 g, 23.7 mmol) was mixed with Eaton's reagent (47.5 mL, 3 g per mmol of carboxylic acid 9) and stirred for 72 h at room temperature. The mixture was then poured over ice, neutralized, and extracted with EtOAc (3×75 mL). The organic layer was dried over sodium sulfate, concentrated and purified by flash chromatography using a prepacked 100 g silica column [solvent A: EtOAc; solvent B: hexane; gradient: 7% A/93% B (1 CV), 7% A/93% B?60% A/40% B (10 CV), 60% A/40% B (2 CV); flow rate: 40 mL/min; monitored at 254 nm and 280 nm] to afford ketone 11 (2.01 g, 10.5 mmol, 44%) as a yellow solid. 1H NMR (CDCl3, 600 MHz) delta 7.06 (1H, d, J=8.4 Hz), 6.62 (1H, d, J=8.4 Hz), 3.61 (3H, s), 3.57 (3H, s), 2.70 (2H, t, J=5.4 Hz), 2.25 (2H, t, J=5.4 Hz). 13C NMR (CDCl3, 150 MHz) delta 204.6, 157.1, 147.4, 145.0, 130.7, 119.4, 112.0, 59.8, 55.8, 36.0, 22.1.
With PPA; EXAMPLE 2 4,5-Dimethoxy-1-indanone A reaction mixture of 14.3 g. of 3-(2,3-dimethoxyphenyl)propionic acid and 128 g. of polyphosphoric acid, was stirred with a glass rod at 85-87 C. for 10 minutes. The reaction mixture was poured onto approximately 500 g. of ice and stirred for thirty minutes. The mixture was then filtered and the residue was washed with approximately equal volume portions of water, a saturated aqueous sodium hydroxide solution and then water. The residue was dried in vacuo, to yield 8.1 g. of 4,5-dimethoxy-1-indanone as a brown solid. M.P. 73-74 C.
In methanesulfonic acid; b) 2,3-Dihydro-4,5-dimethoxy-1H-inden-1-one Under nitrogen a solution of 3-(2,3-dimethoxyphenyl)-propanoic acid (2 g) in 50 ml methanesulfonic acid was warmed at 60 0C and kept there for 2 hours. The reaction mixture was cooled to room temperature and poured into ice/water. After extraction with ethyl acetate the organic layer was washed with a 1N aqueous sodium hydroxyde solution, dried over magnesium sulfate, filtered and evaporated in vacuo yielding 1.2g of 2,3-dihydro-4,5-dimethoxy-1H-inden-1-one, M.S. (C.I.) (M/Z): 193 [M+H]+.
  • 3
  • [ 43014-31-9 ]
  • [ 6342-80-9 ]
  • 4
  • [ 6342-80-9 ]
  • [ 105-36-2 ]
  • (6,7-dimethoxy-inden-3-yl)-acetic acid ethyl ester [ No CAS ]
  • 5
  • [ 6342-80-9 ]
  • [ 105-56-6 ]
  • [ 100067-46-7 ]
  • 6
  • [ 6342-80-9 ]
  • [ 66487-71-6 ]
YieldReaction ConditionsOperation in experiment
72% With trimethylammonium heptachlorodialuminate; In dichloromethane; at 80℃; for 1h;Microwave irradiation; Ketone 11 (0.70 g, 3.2 mmol) was added to a 20 mL microwave vial with [TMAH] [Al2Cl7] (10.0 mL, 7.26 mmol) and microwaved for 1 h at 80 C. The mixture was poured into water, extracted with CH2Cl2 (3×30 mL), dried over sodium sulfate and purified by flash chromatography using a prepacked 50 g silica column [solvent A: EtOAc; solvent B: hexane; gradient: 12% A/88% B (1 CV), 12% A/88% B?100% A/0% B (10 CV), 100% A/0% B (2 CV); flow rate: 50 mL/min; monitored at 254 nm and 280 nm] to afford phenol 15 (0.42 g, 2.36 mmol, 72%) as a brown solid. 1H NMR (CDCl3, 600 MHz) delta 7.35 (1H, d, J=10.2 Hz), 6.92 (1H, d, J=10.2 Hz), 5.81 (1H, s), 3.97 (3H, s), 3.07 (2H, t, J=6.6 Hz), 2.69 (2H, t, J=6.6 Hz). 13C NMR (CDCl3, 150 MHz) delta 206.0, 150.9, 142.1, 140.5, 131.4, 116.1, 110.4, 56.4, 36.5, 21.9.
aluminium trichloride; In 1,2-dichloro-ethane; c) 2,3-Dihydro-4-hydroxy-5-methoxy-1H-inden-1-one Under a nitrogen atmosphere <strong>[6342-80-9]2,3-dihydro-4,5-dimethoxy-1H-inden-1-one</strong> (31.7 g) was dissolved in 600 ml of anhydrous 1,2-dichloroethane and cooled to 0 0C. Aluminum chloride (44 g) was added in portions and the reaction mixture was heated to 60 0C for 17 hours, cooled to room temperature and poured into ice/water. After extraction with dichloromethane the organic layer was dried and evaporated. The residue was crystallized from ethyl acetate to give 20.5 g of 2,3-dihydro-4-hydroxy-5-methoxy-1H-inden-1-one, M.S. (C.I.) (M/Z): 179 [M+H]+.
  • 7
  • [ 6342-80-9 ]
  • [ 7677-24-9 ]
  • [ 100449-12-5 ]
  • 8
  • [ 6342-80-9 ]
  • [ 7677-24-9 ]
  • [ 956100-50-8 ]
YieldReaction ConditionsOperation in experiment
73% zinc(II) iodide; In toluene; acetonitrile; at 50℃; for 16h; Under nitrogen, zinc iodide (1.5 g, 4.68 mmol), trimethylsilyl cyanide (27.1 ml_, 203.0 mmol) were added sequentially to the solution of <strong>[6342-80-9]4,5-dimethoxy-1-indanone</strong> (30.0 g, 156.1 mmol) in toluene (100 ml_) and acetonitrile (24 mL). The reaction mixture was heated to 5O0C for 16 h. The reaction mixture was cooled to room temperature and diluted with 100 mL of toluene and 60 mL of a saturated aqueous sodium bicarbonate solution. After the mixture was stirred for 1 h, the layers were separated. The organic layer was washed by brine (60 mL) and dried (Na2SO4). The organic layer was concentrated in vacuo and the residue was purified by chromatography (EtOAc / Hexanes: 5/95) to afford 1-trimethylsilanyloxy-4,5- dimethoxyindane-1-carbonitrile (33.1 g, 73%).
  • 11
  • [ 6342-80-9 ]
  • [ 38489-91-7 ]
  • 12
  • [ 6342-80-9 ]
  • [ 83864-36-2 ]
  • 15
  • [ 141-82-2 ]
  • [ 86-51-1 ]
  • [ 6342-80-9 ]
  • 16
  • [ 6342-80-9 ]
  • [ 120-14-9 ]
  • 2-<(3,4-Dimethoxyphenyl)methylen>-4,5-dimethoxy-indan-1-on [ No CAS ]
  • 17
  • [ 6342-80-9 ]
  • [ 22065-85-6 ]
  • 2-[1-(1-Benzyl-piperidin-4-yl)-meth-(Z)-ylidene]-4,5-dimethoxy-indan-1-one [ No CAS ]
  • 19
  • [ 6342-80-9 ]
  • [ 42796-28-1 ]
  • paraformaldehyde [ No CAS ]
  • [ 125706-62-9 ]
  • 20
  • [ 6342-80-9 ]
  • [ 6091-44-7 ]
  • paraformaldehyde [ No CAS ]
  • [ 125706-61-8 ]
  • 21
  • [ 6342-80-9 ]
  • [ 66487-71-6 ]
  • 5-hydroxy-4-methoxy-indan-1-one [ No CAS ]
  • 22
  • [ 6342-80-9 ]
  • [ 537690-40-7 ]
  • 23
  • [ 6342-80-9 ]
  • [ 73568-29-3 ]
  • 2-[1-(2-Chloro-6-methoxy-quinolin-3-yl)-meth-(E)-ylidene]-4,5-dimethoxy-indan-1-one [ No CAS ]
  • 24
  • [ 6342-80-9 ]
  • [ 68236-20-4 ]
  • 2-[1-(2-Chloro-7-methoxy-quinolin-3-yl)-meth-(E)-ylidene]-4,5-dimethoxy-indan-1-one [ No CAS ]
  • 25
  • [ 6342-80-9 ]
  • [ 68236-25-9 ]
  • 2-[1-(2-Chloro-5,6,7-trimethoxy-quinolin-3-yl)-meth-(E)-ylidene]-4,5-dimethoxy-indan-1-one [ No CAS ]
  • 26
  • [ 6342-80-9 ]
  • (+/-)-2-iodo-4,5-dimethoxyindan-1-one [ No CAS ]
  • 27
  • [ 848610-54-8 ]
  • [ 6342-80-9 ]
  • 28
  • [ 6342-80-9 ]
  • [ 68236-23-7 ]
  • 2-[1-(2-Chloro-6,7-dimethoxy-quinolin-3-yl)-meth-(E)-ylidene]-4,5-dimethoxy-indan-1-one [ No CAS ]
  • 29
  • [ 6342-80-9 ]
  • [ 615-43-0 ]
  • 1,2-dimethoxy-5,10-dihydro-indeno[1,2-b]indole [ No CAS ]
  • [ 62-53-3 ]
  • 31
  • [ 6342-80-9 ]
  • [ 700348-67-0 ]
  • 32
  • [ 6342-80-9 ]
  • C29H28O3 [ No CAS ]
  • 33
  • [ 6342-80-9 ]
  • C29H24O3 [ No CAS ]
  • 35
  • [ 6342-80-9 ]
  • [ 213008-03-8 ]
 

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