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Chemical Structure| 606-23-5 Chemical Structure| 606-23-5

Structure of 606-23-5

Chemical Structure| 606-23-5

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Product Details of [ 606-23-5 ]

CAS No. :606-23-5
Formula : C9H6O2
M.W : 146.14
SMILES Code : O=C1CC(C2=C1C=CC=C2)=O
MDL No. :MFCD00003779
InChI Key :UHKAJLSKXBADFT-UHFFFAOYSA-N
Pubchem ID :11815

Safety of [ 606-23-5 ]

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

Computational Chemistry of [ 606-23-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.11
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 39.91
TPSA ?

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

34.14 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.3
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

0.61
Log Po/w (WLOGP)?

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

1.46
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.

0.69
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

2.45
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.3

Water Solubility

Log S (ESOL):?

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

-1.53
Solubility 4.27 mg/ml ; 0.0292 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-0.9
Solubility 18.4 mg/ml ; 0.126 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

-2.98
Solubility 0.152 mg/ml ; 0.00104 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.

-6.76 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.

1.0 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<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)

1.27

Application In Synthesis of [ 606-23-5 ]

* 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 [ 606-23-5 ]

[ 606-23-5 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 606-23-5 ]
  • [ 6414-69-3 ]
  • 7,12-dioxo-7,12-dihydro-indeno[1,2-<i>a</i>]fluorene-5-carboxylic acid ethyl ester [ No CAS ]
  • 2
  • [ 606-23-5 ]
  • [ 28710-97-6 ]
  • 3-(<5'-oxo-1'-phenylpyrazol-2'-in-3'yl>amino)inden-1-one [ No CAS ]
  • 3
  • [ 606-23-5 ]
  • [ 42059-80-3 ]
  • 2-(6-Nitro-4-oxo-4H-chromen-3-ylmethylene)-indan-1,3-dione [ No CAS ]
  • 4
  • [ 606-23-5 ]
  • [ 63874-95-3 ]
  • 2-(1-benzyl-1H-pyrazol-4-ylmethylene)-1H-indene-1,3(2H)-dione [ No CAS ]
  • 5
  • [ 606-23-5 ]
  • [ 34595-26-1 ]
  • 2′,3′,4′,4a′-tetrahydro-1′H,6′H-spiro[indene-2,5′-pyrido[1,2-a]quinoline]-1,3-dione [ No CAS ]
  • 6
  • [ 606-23-5 ]
  • [ 33985-71-6 ]
  • [ 135838-92-5 ]
YieldReaction ConditionsOperation in experiment
79% In ethanol; at 50℃; for 4h; By the adoption of the following formula 1a compound of the desired: the 1, 2, 3, 5, 6, 7-hexahydro-pyrido [3, 2, 1-ij] quinoline-9-formaldehyde (4.02g) and compound 1H-indene -1,3 (2H)-dione (2.92g) in ethanol solvent (150 ml) in 50 C stirring in the backflow 4 hours, the solid obtained from the same filter, the chemical purification by column chromatography, recrystallization, and a (its yield = 79%).
  • 7
  • [ 606-23-5 ]
  • [ 1128-56-9 ]
  • [ 123-11-5 ]
  • [ 1001090-98-7 ]
  • 8
  • [ 606-23-5 ]
  • [ 28710-97-6 ]
  • [ 123-11-5 ]
  • 2-phenyl-4-(4-methoxyphenyl)-1,2-dihydro-5H-indeno[1,2-b]pyrazolo[4,3-e]pyridin-3,5-dione [ No CAS ]
  • 10
  • [ 606-23-5 ]
  • [ 100643-27-4 ]
  • [ 667463-64-1 ]
  • [ 1258795-91-3 ]
  • 11
  • [ 606-23-5 ]
  • [ 667463-64-1 ]
  • [ 5356-71-8 ]
  • [ 1315268-75-7 ]
  • 12
  • [ 606-23-5 ]
  • [ 42906-19-4 ]
  • 2-[4-(Di-p-tolyl-amino)-benzylidene]-indan-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% In butan-1-ol; at 120℃; for 2h; General procedure: 1,3-Indandione (0.19 g, 1.3 mmol) and 4-[bis(4-methoxyphenyl)amino]benzaldehyde (a) (0.4 g 1.43 mmol) were dissolved in 22 mL of butan-1-ol and refluxed for 2 h. Then the mixture was cooled down to the room temperature. The solid precipitate was collected and recrystallized from butan-1-ol to give 0.53 g of red crystals (65percent yield).
  • 13
  • [ 606-23-5 ]
  • [ 41042-12-0 ]
  • [ 36646-77-2 ]
  • C33H28N2O4 [ No CAS ]
  • 14
  • [ 606-23-5 ]
  • [ 41042-12-0 ]
  • [ 41609-04-5 ]
  • C33H28N2O3 [ No CAS ]
  • 15
  • [ 606-23-5 ]
  • [ 41042-12-0 ]
  • 3-[(4-bromophenyl)amino]cyclohex-2-en-1-one [ No CAS ]
  • C32H25BrN2O3 [ No CAS ]
  • 16
  • [ 1004-38-2 ]
  • [ 606-23-5 ]
  • [ 1620054-90-1 ]
  • 2,4-diamino-5-(2-butoxy-7-chloroquinolin-3-yl)-5H-indeno[2',1':5,6]pyrido[2,3-d]pyrimidin-6(11H)-one [ No CAS ]
  • 17
  • [ 1004-38-2 ]
  • [ 606-23-5 ]
  • C17H12ClNO2 [ No CAS ]
  • C30H21ClN6O2 [ No CAS ]
  • 18
  • [ 606-23-5 ]
  • [ 126712-07-0 ]
  • 2-(6-bromo-2-methoxybenzylidene)-1H-indene-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% General procedure: In a round bottomed flask, indane-1,3-dione (1 mmol) was dissolvedin pyridine (5 mL) and stirred for 5-10 min. Then substituted benzaldehyde(1 mmol) was added and the reaction mixture was refluxed for1 h at 100 C. The reaction progress was monitored by TLC. Aftercompletion, the reaction mixture was brought to room temperature andthen poured onto ice cold water. The resulting precipitates were filteredand washed thoroughly with hexane. The precipitates were crystallizedfrom methanol.
  • 19
  • [ 2631-77-8 ]
  • [ 606-23-5 ]
  • C16H8I2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With L-proline; In methanol; at 20℃; General procedure: A solution of 1,3-indanedione (5 mmol, 1eq), substituted salicylaldehyde (5 mmol, 1eq) and L-proline ( 30 mol%, 1.5 mmol, 0.3eq) in methanol (15ml) was stirred at room temperature until a precipitate formed. The formed precipitate was filtered and washed several times with methanoland diethyl ether to afford the 2-hydoxybenzylidineindenediones. The products were used for the next step without further purification.
 

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