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Chemical Structure| 101382-55-2 Chemical Structure| 101382-55-2
Chemical Structure| 101382-55-2

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2-Hydroxy-7-methoxyquinoline-3-carbaldehyde

CAS No.: 101382-55-2

4.5 *For Research Use Only !

Cat. No.: A440191 Purity: 95%

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Product Details of [ 101382-55-2 ]

CAS No. :101382-55-2
Formula : C11H9NO3
M.W : 203.19
SMILES Code : O=CC1=CC2=CC=C(OC)C=C2N=C1O
MDL No. :MFCD02986395
InChI Key :VUKFTGRTRKQOKY-UHFFFAOYSA-N
Pubchem ID :600262

Safety of [ 101382-55-2 ]

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

Calculated chemistry of [ 101382-55-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 10
Fraction Csp3 0.09
Num. rotatable bonds 2
Num. H-bond acceptors 4.0
Num. H-bond donors 1.0
Molar Refractivity 55.65
TPSA ?

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

59.42 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.88
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

2.15
Log Po/w (WLOGP)?

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

1.76
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.

0.64
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

2.09
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.7

Water Solubility

Log S (ESOL):?

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

-2.82
Solubility 0.311 mg/ml ; 0.00153 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.

-3.03
Solubility 0.19 mg/ml ; 0.000933 mol/l
Class?

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

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

-3.21
Solubility 0.126 mg/ml ; 0.000619 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.

-6.01 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<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)

1.46

Application In Synthesis [ 101382-55-2 ]

* 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 [ 101382-55-2 ]

[ 101382-55-2 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 68236-20-4 ]
  • [ 101382-55-2 ]
YieldReaction ConditionsOperation in experiment
90% With acetic acid; for 10h;Heating; A stirred solution of 2 (1g, 4.51 mmol) in AcOH (90 mL) was heated to 95 oC for 10 h.The reaction mixture was poured into crushed ice and stirred for 30 min. The resultingsolid was filtered, washed with water, and dried to afford 7-methoxy-2-oxo-1,2-dihydroquinoline-3-carbaldehyde (3) (0.80 g, 90%).
76% With acetic acid; at 110℃; for 16h; A suspension of 2-chloro-7-methoxyquinoline-3-carbaldehyde (8.Og, 36.2 mmol) in 70% acetic acid (370 mL) was heated to 110 C for 16h. Upon cooling the reaction mixture to roomtemperature and poured into crushed ice ;solid was filtered off and washed with water, dried under reduced pressure for overnight to give title compound as pale yellow solid (5.6 g, 76%).1H NMR (400 MHz, DMSO-d6) oe 12.07 (s, 1H), 10.18 (s, 1H), 8.43 (s, 1H), 7.84 (d, J=8.9 Hz, 1H), 6.89 (dd, J=2.5 Hz, 8.8 Hz, 1H), 6.82 (d, J=1.9 Hz, 1H), 3.86 (s, 3H); LC-MS: mz 204.1 (M+1).
76% With acetic acid; at 110℃; for 16h; Step-c Synthesis of 7-methoxy-2-oxo-1,2-dihydroquinoline-3-carbaldehyde A suspension of 2-chloro-7-methoxyquinoline-3-carbaldehyde (8.0 g, 36.2 mmol) in 70% acetic acid (370 mL) was heated to 110 C. for 16 h. Upon cooling the reaction mixture to room temperature and poured into crushed ice;solid was filtered off and washed with water, dried under reduced pressure for overnight to give title compound as pale yellow solid (5.6 g, 76%). 1H NMR (400 MHz, DMSO-d6) delta 12.07 (s, 1H), 10.18 (s, 1H), 8.43 (s, 1H), 7.84 (d, J=8.9 Hz, 1H), 6.89 (dd, J=2.5 Hz, 8.8 Hz, 1H), 6.82 (d, J=1.9 Hz, 1H), 3.86 (s, 3H); LC-MS: m/z 204.1 (M+1)+.
  • 2
  • [ 141-82-2 ]
  • [ 101382-55-2 ]
  • [ 101382-61-0 ]
  • 3
  • [ 114-70-5 ]
  • [ 101382-55-2 ]
  • 7-Methoxy-3-phenyl-1-oxa-9-aza-anthracen-2-one [ No CAS ]
  • 4
  • [ 101382-55-2 ]
  • [ 543-24-8 ]
  • N-(7-Methoxy-2-oxo-2H-1-oxa-9-aza-anthracen-3-yl)-acetamide [ No CAS ]
  • 6
  • [ 101382-55-2 ]
  • [ 116704-97-3 ]
  • 7
  • [ 106-96-7 ]
  • [ 101382-55-2 ]
  • N-propargyl-3-formyl-7-methoxy-2-quinolone [ No CAS ]
  • 9
  • [ 141-82-2 ]
  • [ 101382-55-2 ]
  • (Z)-3-(7-Methoxy-2-oxo-1,2-dihydro-quinolin-3-yl)-acrylic acid [ No CAS ]
  • 10
  • [ 141-82-2 ]
  • [ 101382-55-2 ]
  • 3-(7-methoxy-2-oxo-1,2-dihydro-quinolin-3-yl)-acrylic acid [ No CAS ]
  • 11
  • [ 106-95-6 ]
  • [ 101382-55-2 ]
  • [ 950834-74-9 ]
  • 12
  • [ 101382-55-2 ]
  • C14H14INO3 [ No CAS ]
  • 14
  • [ 101382-55-2 ]
  • 3-(2-chloro-7-methoxy-quinolin-3-yl)-acryloyl chloride [ No CAS ]
  • 15
  • [ 101382-55-2 ]
  • 3-(2-chloro-7-methoxy-quinolin-3-yl)-acrylic acid [ No CAS ]
  • 16
  • [ 101382-55-2 ]
  • 3-(2-chloro-7-methoxy-quinolin-3-yl)-acrylic acid ethyl ester [ No CAS ]
  • 17
  • [ 101382-55-2 ]
  • 3-(7-methoxy-2-oxo-1,2-dihydro-quinolin-3-yl)-acrylic acid ethyl ester [ No CAS ]
  • 19
  • [ 101382-55-2 ]
  • (Z)-3-(2-Chloro-7-methoxy-quinolin-3-yl)-acrylic acid ethyl ester [ No CAS ]
  • 20
  • [ 101382-55-2 ]
  • (Z)-3-(7-Methoxy-2-oxo-1,2-dihydro-quinolin-3-yl)-acrylic acid ethyl ester [ No CAS ]
  • 22
  • [ 101382-55-2 ]
  • 8-methoxytetrazolo[1,5-a]quinoline-4-carbaldehyde [ No CAS ]
  • 23
  • [ 101382-55-2 ]
  • 2-chloro-7-methoxyquinoline-3-carboxaldoxime [ No CAS ]
  • 24
  • [ 101382-55-2 ]
  • 2-chloro-7-methoxyquinoline-3-carboxalehyde hydrazone [ No CAS ]
  • 25
  • [ 101382-55-2 ]
  • 2-chloro-7-methoxy-3-methoxycarbonylquinoline [ No CAS ]
 

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Technical Information

• Appel Reaction • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Fischer Indole Synthesis • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Jones Oxidation • Julia-Kocienski Olefination • Knoevenagel Condensation • Leuckart-Wallach Reaction • Martin's Sulfurane Dehydrating Reagent • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mitsunobu Reaction • Moffatt Oxidation • Mukaiyama Aldol Reaction • Nomenclature of Ethers • Nozaki-Hiyama-Kishi Reaction • Oxidation of Alcohols by DMSO • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Alcohols • Preparation of Aldehydes and Ketones • Preparation of Amines • Preparation of Ethers • Prins Reaction • Reactions of Alcohols • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Ethers • Reactions with Organometallic Reagents • Reformatsky Reaction • Ritter Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Sharpless Olefin Synthesis • Stetter Reaction • Stobbe Condensation • Swern Oxidation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

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