38480-94-3|2',3'-Dimethoxyacetophenone| Ambeed

CAS No. :	38480-94-3
Formula :	C₁₀H₁₂O₃
M.W :	180.20
SMILES Code :	CC(C1=CC=CC(OC)=C1OC)=O
MDL No. :	MFCD03424412
InChI Key :	FODUVZQSLRHUMC-UHFFFAOYSA-N
Pubchem ID :	12407413

Safety of [ 38480-94-3 ]

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

Computational Chemistry of [ 38480-94-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.3
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	49.62
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	35.53 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.91
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	1.66
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.91
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.	1.13
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	2.19
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.76

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.15
Solubility	1.29 mg/ml ; 0.00714 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.	-2.02
Solubility	1.72 mg/ml ; 0.00955 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	-2.99
Solubility	0.186 mg/ml ; 0.00103 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.	-6.22 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)	1.55

Application In Synthesis of [ 38480-94-3 ]

* 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 [ 38480-94-3 ]

[ 38480-94-3 ] Synthesis Path-Downstream 1~55

1
[ 917-64-6 ]
[ 5653-62-3 ]
[ 38480-94-3 ]

References: [1]Journal of the Chemical Society,1936,p. 346.

2
[ 38480-94-3 ]
[ 13494-10-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	With boron tribromide; In methanol; dichloromethane; ethyl acetate;	18G 2',3'-Dihydroxyacetophenone A solution of <strong>[38480-94-3]2',3'-dimethoxyacetophenone</strong> (4.85 g, 26.9 mmol) in dichloromethane (100 ml) was added at -70° C. with a 1M boron tribromide solution in dichloromethane (68 ml). The mixture was left to cool, keeping stirring for 2.5 hours at room temperature, then added with methanol (70 ml), left under stirring for 1 h, thereafter evaporated to dryness. The residue was dissolved in ethyl acetate (250 ml), washed with 2percent NaHCO3 (1*30 ml), dried and the solvent was evaporated off, to obtain a crude which was purified by crystallization in methanol, thereby obtaining 3.10 g of the title compound as a yellow solid (76percent yield). 1 H N.M.R. (300 MHz, CDCl3) delta ppm: 2.61 (s, 3H); 7.05-6.77 (t, 1H); 7.02 (dd, 1H); 7.36 (dd, 1H).

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 183 - 192.
[2]Patent: US5990142,1999,A .
[3]Chemische Berichte,1913,vol. 46,p. 4019.
[4]Chemische Berichte,1913,vol. 46,p. 4019.
[5]Journal of the American Chemical Society,2005,vol. 127,p. 10371 - 10387.

3
[ 38480-94-3 ]
[ 703-98-0 ]

References: [1]Journal of Chemical Research,2010,p. 222 - 227.
[2]Journal of the American Chemical Society,1951,vol. 73,p. 793.
[3]Helvetica Chimica Acta,1927,vol. 10,p. 389.

4
[ 38480-94-3 ]
[ 103517-22-2 ]

References: [1]Chemische Berichte,1916,vol. 49,p. 1265.

5
[ 38480-94-3 ]
[ 121704-80-1 ]

References: [1]Chemische Berichte,1916,vol. 49,p. 1265.

6
[ 38480-94-3 ]
2,2-dibromo-1-(2,3-dimethoxy-phenyl)-ethanone [ No CAS ]

References: [1]Chemische Berichte,1916,vol. 49,p. 1265.

7
[ 6848-73-3 ]
[ 38480-94-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium dichromate; sulfuric acid; In water;	18F 2',3'-Dimethoxyacetophenone A solution of potassium dichromate (24.76 g), water (124 ml) and concentrated sulfuric acid (12 ml) was added with 2-(2,3-dimethoxyphenyl)ethan-2-ol (10.06 g, 55.3 mmol) and left under stirring at room temperature for 15 min. After that the mixture was extracted with ethyl ether and washed successively with a 5percent potassium carbonate solution (2150 ml) and with a sodium chloride saturated solution (1100 ml). The solvent was dried and evaporated under reduced pressure to obtain a residue which was purified by distillation under high vacuum. At a pressure of 0.3 torr and at a temperature of 85° C., 6.47 g of the title compound distiled (65percent yield). 1 H N.M.R. (300 MHz, CDCl3) delta ppm: 2.62 (s, 3H); 3.88 (s, 3H); 3.90 (s, 3H); 7.05-7.10 (sc, 2H); 7.21 (dd, 1H).

References: [1]Patent: US5990142,1999,A .
[2]Journal of the American Chemical Society,1951,vol. 73,p. 793.
[3]Chemische Berichte,1913,vol. 46,p. 4019.
[4]Journal of the American Chemical Society,2005,vol. 127,p. 10371 - 10387.

8
[ 141-97-9 ]
[ 7169-06-4 ]
[ 38480-94-3 ]

References: [1]Proceedings - Indian Academy of Sciences, Section A,1953,p. 480,490.

9
[ 38480-94-3 ]
[ 100-10-7 ]
4-dimethylamino-2',3'-dimethoxy-chalcone [ No CAS ]

References: [1]Helvetica Chimica Acta,1924,vol. 7,p. 335.

10
[ 105-53-3 ]
[ 7169-06-4 ]
[ 38480-94-3 ]

References: [1]Journal of the American Chemical Society,1955,vol. 77,p. 2894.
[2]Nippon Kagaku Zasshi,1953,vol. 74,p. 654.
Chem.Abstr.,1954,p. 12027.

11
[ 506-82-1 ]
[ 7169-06-4 ]
[ 38480-94-3 ]

References: [1]Journal of the American Chemical Society,1942,vol. 64,p. 2859,2860.

12
[ 38480-94-3 ]
[ 86-51-1 ]
2,3,2',3'-tetramethoxy-<i>trans</i>-chalcone [ No CAS ]

References: [1]Journal of the American Chemical Society,1954,vol. 76,p. 4486.

13
[ 50-00-0 ]
[ 38480-94-3 ]
[ 506-59-2 ]
1-(3-dimethylaminopropionyl)-2,3-dimethoxybenzene hydrochloride [ No CAS ]

References: [1]Pharmaceutical Chemistry Journal,1993,vol. 27,p. 499 - 500.
Khimiko-Farmatsevticheskii Zhurnal,1993,vol. 27,p. 36 - 37.

14
[ 38480-94-3 ]
[ 100-52-7 ]
(E)-1-(2,3-Dimethoxy-phenyl)-3-phenyl-propenone [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 1434 - 1442.

15
[ 93-89-0 ]
[ 38480-94-3 ]
[ 93213-66-2 ]

References: [1]Journal of Organic Chemistry,1960,vol. 25,p. 1333 - 1336.

16
[ 38480-94-3 ]
(R)-1-(2,3-Dimethoxy-phenyl)-ethanol [ No CAS ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 5329 - 5332.

20
<2,3-dimethoxy-benzoyl>-acetic acid ester [ No CAS ]
[ 38480-94-3 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1926,vol. <2> 112,p. 63.

21
[ 6848-73-3 ]
diluted Cr₂O₃-H₂SO₄ [ No CAS ]
[ 38480-94-3 ]

References: [1]Chemische Berichte,1913,vol. 46,p. 4019.

22
[ 38480-94-3 ]
hydrochloride of hydroxylamine [ No CAS ]
[ 23997-79-7 ]

References: [1]Chemische Berichte,1913,vol. 46,p. 4019.

23
[ 7647-01-0 ]
[ 38480-94-3 ]
amalgamated zinc [ No CAS ]
[ 103517-22-2 ]

References: [1]Chemische Berichte,1916,vol. 49,p. 1265.

24
[ 7664-93-9 ]
[ 528830-98-0 ]
[ 38480-94-3 ]