39989-39-4|7-Methoxyisoquinoline| Ambeed

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Quality Control of [ 39989-39-4 ] Purity: 95% SDS Specification

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Product Details of [ 39989-39-4 ]

CAS No. :	39989-39-4
Formula :	C₁₀H₉NO
M.W :	159.19
SMILES Code :	COC1=CC2=C(C=C1)C=CN=C2
MDL No. :	MFCD09030747
InChI Key :	PNNUXNXZDJVGSB-UHFFFAOYSA-N
Pubchem ID :	594375

Safety of [ 39989-39-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 39989-39-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	10
Fraction Csp3	0.1
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	48.24
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	22.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.96
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.22
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.24
Log P_o/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.	1.22
Log P_o/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	2.46
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.02

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.78
Solubility	0.266 mg/ml ; 0.00167 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.	-2.32
Solubility	0.763 mg/ml ; 0.00479 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	-3.82
Solubility	0.0243 mg/ml ; 0.000153 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.	-5.69 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)	1.13

Application In Synthesis of [ 39989-39-4 ]

* 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 [ 39989-39-4 ]

[ 39989-39-4 ] Synthesis Path-Downstream 1~37

1
[ 39989-39-4 ]
[ 75-03-6 ]
[ 112435-03-7 ]

References: [1]Journal of Heterocyclic Chemistry,1987,vol. 24,p. 715 - 719.
[2]Justus Liebigs Annalen der Chemie,1895,vol. 286,p. 16.

2
[ 39989-39-4 ]
[ 74-88-4 ]
[ 53366-09-9 ]

References: [1]Justus Liebigs Annalen der Chemie,1895,vol. 286,p. 16.

3
[ 39989-39-4 ]
[ 43207-78-9 ]

References: [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 783 - 794.
[2]Justus Liebigs Annalen der Chemie,1895,vol. 286,p. 16.
[3]Journal of the Chemical Society,1958,p. 1967,1973.
[4]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1959,vol. 79,p. 329,334.
Chem.Abstr.,1959,p. 16177.
[5]Biochemical Pharmacology,1995,vol. 50,p. 1903 - 1912.
[6]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 185 - 189.
[7]Journal of Medicinal Chemistry,2005,vol. 48,p. 3586 - 3604.

4
[ 39989-39-4 ]
[ 146607-34-3 ]

References: [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 2602 - 2604.
[2]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1959,vol. 79,p. 329,334.
Chem.Abstr.,1959,p. 16177.

5
[ 39989-39-4 ]
[ 63485-75-6 ]

References: [1]Heterocycles,1993,vol. 36,p. 101 - 105.
[2]Journal of the American Chemical Society,1953,vol. 75,p. 3597.

6
[ 39989-39-4 ]
[ 36016-40-7 ]
[ 84900-37-8 ]

References: [1]Chemical and Pharmaceutical Bulletin,1982,vol. 30,p. 3764 - 3769.

7
[ 39989-39-4 ]
[ 107-08-4 ]
[ 112435-02-6 ]

References: [1]Journal of Heterocyclic Chemistry,1987,vol. 24,p. 715 - 719.

8
[ 39989-39-4 ]
[ 67-68-5 ]
[ 76143-84-5 ]

References: [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 2602 - 2604.

9
[ 39964-88-0 ]
[ 39989-39-4 ]
[ 90806-58-9 ]

References: [1]Journal of Chemical Research, Miniprint,1987,p. 501 - 526.
[2]Journal of Chemical Research, Miniprint,1987,p. 501 - 526.

10
[ 61190-11-2 ]
[ 39989-39-4 ]

References: [1]Heterocycles,1980,vol. 14,p. 1151 - 1154.

11
(E)-3-{2-[(E)-tert-Butylimino-methyl]-4-methoxy-phenyl}-acrylonitrile [ No CAS ]
[ 39989-39-4 ]
[ 74-90-8 ]
[ 115-11-7 ]

References: [1]Tetrahedron Letters,1982,vol. 23,p. 4281 - 4284.

12
[[(2,2-Dimethoxy-ethyl)-ethoxycarbonyl-amino]-(3-methoxy-phenyl)-methyl]-phosphonic acid dimethyl ester [ No CAS ]
[ 39989-39-4 ]

References: [1]Journal of Organic Chemistry,1983,vol. 48,p. 3344 - 3346.

13
(E)-3-{2-[(E)-tert-Butylimino-methyl]-4-methoxy-phenyl}-acrylonitrile [ No CAS ]
[ 39989-39-4 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1317 - 1324.

14
[ 84900-37-8 ]
[ 39989-39-4 ]
8-Methoxy-3H-benzo[d][1,2]diazepine [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1982,vol. 30,p. 3764 - 3769.

15
[ 39989-39-4 ]
[ 116256-19-0 ]
(R)-3-Methoxy-17-oxo-16,17-dihydro-9H,15H-11-oxa-8-aza-cyclopenta[a]phenanthrene-12,12-dicarboxylic acid diethyl ester [ No CAS ]

References: [1]Il Farmaco,1995,vol. 50,p. 137 - 141.

16
[ 39989-39-4 ]
[ 116256-18-9 ]
(R)-8-Methoxy-1-oxo-1,2,3,4-tetrahydro-10bH-11-oxa-4b-aza-chrysene-12,12-dicarboxylic acid diethyl ester [ No CAS ]

References: [1]Il Farmaco,1995,vol. 50,p. 137 - 141.

17
[ 39964-84-6 ]
[ 39989-39-4 ]

References: [1]Synthetic Communications,1999,vol. 29,p. 1617 - 1625.

Yield	Reaction Conditions	Operation in experiment
67%		II. Synthesis of 7-Methoxyisoquinoline To a 2 liter round bottom flask equipped with a magnetic stir bar, condenser and nitrogen inlet is added (75 g, 0.184 mole) of N-(2,2-diethoxyethyl)-N-[(3-methoxyphenyl)methyl]-4-methyl-benzenesulfonamide, 1.0 liter of dioxane and 200 ml of 6N HCl. This slurry is stirred and heated at reflux under nitrogen for 18 hours. The reaction solution is then slowly poured into 1 liter of H2 O and stirred for an additional 30 minutes then extracted with ether (2*500 ml). The pH of the aqueous layer is adjusted to 8 with ammonium hydroxide, the product is extracted with dichloromethane. The combined organics extracts are dried over MgSO4, filtered and evaporated to yield 30 g of an oil. The crude product is purified by chromatography with 12.0% acetone in dichloromethane to provide the product (19.7 g) in a 67% yield.
67%		II. Synthesis of 7-Methoxyisoquinoline To a 2 liter round bottom flask equipped with a magnetic stir bar, condenser and nitrogen inlet is added (75 g, 0.184 mole) of N-(2,2-diethoxyethyl)-N-[(3-methoxyphenyl)methyl]-4-methyl-benzenesulfonamide, 1.0 liter of dioxane and 200 ml of 6N HCl. This slurry is stirred and heated at reflux under nitrogen for 18 hours. The reaction solution is then slowly poured into 1 liter of H2 O and stirred for an additional 30 minutes then extracted with ether (2*500 ml). The pH of the aqueous layer is adjusted to 8 with ammonium hydroxide, the product is extracted with dichloromethane. The combined organics extracts are dried over MgSO4, filtered and evaporated to yield 30 g of an oil. The crude product is purified by chromatography with 12.0% acetone in dichloromethane to provide the product (19.7 g) in a 67% yield.
		Step 3: Synthesis of 7-methoxyisoquinoline: 17.8 g (45 mmol) of N-(2,2-dimethoxyethyl)-N-(3-methoxybenzyl)-4-methylbenzenesulfonamide was dissolved in 250 ml of dioxane and 70 ml of 6 N hydrochloric acid. After heating under reflux for 5 hours, the product was treated with ethyl acetate as the extracting solvent in an ordinary manner to obtain the crude product, which was purified according to the silica gel column chromatography to obtain the title compound. Yield: 6.6 g (41 mmol) (91 %) H-NMR (CDCl3) delta 3.94 (3H, s), 7.20 (1H, d), 7.34 (1H, dd), 7.57 (1H, d), 7.70 (1H, d), 8.40 (1H, d), 9.16 (1H, d)

Preparation 84 7-Isoquinolinol A solution of the compound of Preparation 83 (10.16 g, 0.0638 mol) in 48% hydrobromic acid (100 ml) was heated under reflux for 17 hours. The reaction was cooled to room temperature, diluted with water (150 ml) and the solution made neutral with saturated aqueous sodium bicarbonate solution.

19
3-methoxy-benzylidenaminoacetal [ No CAS ]
[ 39989-39-4 ]

References: [1]Justus Liebigs Annalen der Chemie,1895,vol. 286,p. 16.

20
[ 39989-39-4 ]
[ 64-17-5 ]
sodium [ No CAS ]
[ 43207-78-9 ]

References: [1]Justus Liebigs Annalen der Chemie,1895,vol. 286,p. 16.

21
[ 67-56-1 ]
[ 39989-39-4 ]
[ 67335-10-8 ]
8-bromo-7,7-dimethoxy-7,8-dihydroisoquinoline [ No CAS ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 1222 - 1226.

22
3-methoxy-N-(2,2-dimethoxyethyl)benzylidenamine [ No CAS ]
[ 39989-39-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 185 - 189.

23
[ 39989-39-4 ]
[ 19614-12-1 ]
2-(2-bromo-5-methoxybenzyl)-7-methoxyisoquinolinium bromide [ No CAS ]