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Chemical Structure| 2107-69-9 Chemical Structure| 2107-69-9
Chemical Structure| 2107-69-9

*Storage: Sealed in dry,Room Temperature.

5,6-Dimethoxy-2,3-dihydro-1H-inden-1-one

CAS No.: 2107-69-9

4.5 *For Research Use Only !

Cat. No.: A120912 Purity: 98%

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Product Details of [ 2107-69-9 ]

CAS No. :2107-69-9
Formula : C11H12O3
M.W : 192.21
SMILES Code : C1=C2C(=CC(=C1OC)OC)C(CC2)=O
MDL No. :MFCD00003790
InChI Key :IHMQOBPGHZFGLC-UHFFFAOYSA-N
Pubchem ID :75018

Safety of [ 2107-69-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Calculated chemistry of [ 2107-69-9 ] 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.

2.21
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

1.88

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)

1.84

Application In Synthesis [ 2107-69-9 ]

* 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 [ 2107-69-9 ]

[ 2107-69-9 ] Synthesis Path-Downstream   1~2

  • 2
  • [ 872-85-5 ]
  • [ 2107-69-9 ]
  • [ 4803-74-1 ]
YieldReaction ConditionsOperation in experiment
98% With potassium hydroxide; In water; at 25 - 30℃; for 3h;Product distribution / selectivity; Example 1: Process for preparation of 5,6-dimethoxy-2-(4-pyridylmethylene)-l- indanone of formula IVTo a 1 liter round bottom flask equipped with a mechanical stirrer, thermometer pocket, addition funnel and a condenser, charged demineralized water (250ml), 5,6- dimethoxy-l-indanone (25g) and pyridine-4-carboxaldehyde (19.5g). The reaction mixture was stirred for 5 minutes at a temperature of 25C to 30C. To the reaction mixture then charged a solution of potassium hydroxide (5.2g) dissolved in demineralized water (125ml) slowly over period of 2 hours at a temperature of 25 C to 30C. The reaction mixture was further maintained at a temperature of 25C to 30C for 1 hour to obtain the product, 5,6-dimethoxy-2-(4-pyridylmethylene)-l- indanone. The product obtained was then filtered and washed with demineralized water. Dry the product under vacuum at a temperature of 50C to 55C for 10 hours. Yield: 98%Purity: 99.71%
95.8% 5, 6 Dimethoxy indanone (100 grams), Pyridine-4-carboxaldehyde (78.0 grams) and p-toluene sulfonic acid (138.4 grams) were suspended in toluene (1250 ml) and heated to reflux using water separator for 6 hours. The resulting mass was cooled to 25-40 C. and the solid was filtered off under suction. Further the wet solid was suspended in aqueous 10% sodium carbonate solution (1200 ml) and stirred for 30-60 minutes. The resulting pale yellow precipitate solid was filtered off under suction, washed with water (1000 ml) and dried at a temperature of 80 C. to afford 5,6 Dimethoxy-2-(pyridin-4yl)-methylene-indan-lone (Weight: 140 grams, 95.8%).
92.2% With potassium iodide; calcium chloride; In acetone; at 40 - 50℃; for 4h; In a three-necked flask equipped with a condenser and a stirrer, acetone 60 mL, 5,6-dimethoxy-1-indanone was sequentially added.9.6g, anhydrous calcium chloride 5.55g (0.05mol), 4-pyridine formaldehyde 5.89g, potassium iodide 0.96g, stirred at 40 ~ 50 CAfter mixing for 4 h, the basic reaction was completely monitored by HPLC, cooled to room temperature, filtered, and the filtrate was concentrated.Filtration and drying under vacuum gave Compound III 12.96 g, yield 92.2%, HPLC, purity 99.7%.
67% With sodium hydroxide; In ethanol; water; at 20℃;Inert atmosphere; To a solution of 1 mmol of 4-pyridinecarboxaldehyde and 1 mmol of 5,6-dimethoxy-1-indanone in 10 ml EtOH, aqueous solution of NaOH (10%) was added dropwise. The reaction mixture was stirred overnight at room temperature. The obtained solid was fltered and recrystallized from EtOH to give 3 as an of-white solid [22]; yield 67%; mp: 118-120 C; FTIR (KBr) nu3008, 2937, 1691, 1600, 1465, 1315, 1268, 1029 cm-1; 1H NMR (400 MHz, CDCl3): 3.82 (3H, s, OCH3), 3.91 (3H, s, OCH3), 4.03 (2H, s, CH2), 7.17 (1H, s, Ar), 7.22 (1H, s, Ar), 7.42 (1H, s, =CH), 7.67 (2H, d, 3JH-H = 5.36, pyridine-H), 8.64 (2H, d, 3JH-H = 5.46, pyridine-H).
With toluene-4-sulfonic acid; In toluene; for 6h;Heating / reflux; Preparation 1 Preparation of 5, 6-dimethoxy-2- (pyridine-4-yl) methylene-indan-1-one A mixture OF 5, 6-DIMETHOXY-INDAN-1-ONE (100G), pyridine-4-carboxaldehyde (67g), p- toluene sulfonic acid (118G) in toluene (1200ML) was refluxed azeotropically for 6 hours. The reaction mixture was cooled to room temperature and filtered. The wet solid so obtained was stirred with 10% aqueous sodium carbonate solution. The solid was filtered, washed with acetone and then dried to get the title compound (130G). HPLC Purity: 99.5%
With sodium hydroxide; In methanol; at 20℃; for 4h; General procedure: 5,6-dimethoxy-2,3-dihydro-1H-inden-1-one (0.001 mol) with appropriate aldehyde (0.001 mol) in diluted methanolic sodium hydroxide solution was stirred under room temperature for 4 h. The resulting solution was allowed to stand overnight and then the reaction mixture was poured into cold water and neutralized with dilute HCl. The solid was filtered, dried and recrystallized with ethanol furnished the 2-substituted-5,6-dimethoxy-2,3-dihydro-1H-indene-1-one.

 

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