71176-54-0|(5-Amino-1,3-phenylene)dimethanol| Ambeed

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Quality Control of [ 71176-54-0 ] Purity: 95% SDS Specification

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Product Details of [ 71176-54-0 ]

CAS No. :	71176-54-0
Formula :	C₈H₁₁NO₂
M.W :	153.18
SMILES Code :	NC1=CC(CO)=CC(CO)=C1
MDL No. :	MFCD08690090
Boiling Point :	No data available
InChI Key :	YZRLJOVKGWVBHP-UHFFFAOYSA-N
Pubchem ID :	13401257

Safety of [ 71176-54-0 ]

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

Computational Chemistry of [ 71176-54-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	3.0
Molar Refractivity	43.1
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	66.48 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.15
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	-0.53
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.04
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.	0.33
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	0.8
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.34

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.73
Solubility	28.7 mg/ml ; 0.187 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.	-0.4
Solubility	61.4 mg/ml ; 0.401 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	-1.68
Solubility	3.19 mg/ml ; 0.0208 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	No
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	No
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	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.61 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	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)	1.06

Application In Synthesis of [ 71176-54-0 ]

* 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 [ 71176-54-0 ]

[ 71176-54-0 ] Synthesis Path-Downstream 1~35

1
[ 99-31-0 ]
[ 71176-54-0 ]

References: [1]Synthesis,1992,p. 1235 - 1236.
[2]Canadian Journal of Chemistry,2012,vol. 90,p. 138 - 144.
[3]European Journal of Inorganic Chemistry,2017,vol. 2017,p. 3622 - 3634.

2
[ 10560-13-1 ]
[ 71176-54-0 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 535 - 544.

3
[ 108-24-7 ]
[ 71176-54-0 ]
[ 96409-74-4 ]
3,5-Bis(acetoxymethyl)-N-acetyl-2-nitroanilin [ No CAS ]

References: [1]Chemische Berichte,1985,vol. 118,p. 1204 - 1229.

4
[ 71176-54-0 ]
[ 146335-25-3 ]

References: [1]Synthesis,1992,p. 1235 - 1236.

5
[ 71176-55-1 ]
[ 71176-54-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; under 258.58099999999996 Torr; for 2h;	Compound 27:25 26 27[227] To a solution of 5-nitro-m-xylene-alpha,alpha'-diol 25 (1.07 g, 5.84 mmol) in methanol (50 mL) was added Pd/C (10percent, 311 mg, 0.29 mmol). Hydrogen was introduced to replace the air then the mixture was hydrogenated (H2, 5 psi) for 2 hours at room temperature. The solution was filtered through celite and the filtrate was evaporated by rotary evaporation in vacuo to give compound 26 as a white solid (900 mg, y = 100percent). 1H NMR (400 MHz, MeOD): delta 6.71 (s, IH), 6.66 (s, 2H), 4.51 (s, 4H); 13C NMR (400 MHz, MeOD): delta 148.9, 143.8, 116.7, 114.3, 65.5; It was dissolved in anhydrous acetonitrile (30 mL) and ethyl bromoacetate (443 mul, 4.67 mmol) and potassium carbonate (807 mg, 5.84 mmol) were added. The mixture was put in a 86 0C oil bath and refluxed for 17 hours. The reaction mixture was removed from the oil bath, cooled to room temperature and diluted with dichloromethane. It was filtered through celite and the solid was washed with dichloromethane. White precipitate appeared in the filtrate. It was col]ected by filtration to give compound 27 (414 mg, y = 39percent) as a white solid. 1H NMR (400 MHz, MeOD): delta 6.67 (s, IH), 6.53 (s, 2H), 4.51 (s, 4H), 3.94 (s, 2H), 3.73 (s, 3H); 13C NMR (400 MHz, MeOD): delta 174.0, 149.7, 143.9, 116.2, 111.6, 65.6, 52.6, 46.5; MS (m/z): found 248.0 (M + Na)+.

References: [1]Patent: WO2010/91150,2010,A1 .Location in patent: Page/Page column 119-120.
[2]Chemische Berichte,1985,vol. 118,p. 1204 - 1229.

6
[ 42122-73-6 ]
[ 71176-54-0 ]

References: [1]European Journal of Inorganic Chemistry,2017,vol. 2017,p. 3622 - 3634.
[2]Journal of the American Chemical Society,1999,vol. 121,p. 9531 - 9538.
[3]Nucleosides and Nucleotides,1999,vol. 18,p. 291 - 305.
[4]Canadian Journal of Chemistry,2012,vol. 90,p. 138 - 144.

7
CCuN*CNNa [ No CAS ]
[ 71176-54-0 ]
[ 146335-23-1 ]

References: [1]Nucleosides and Nucleotides,1999,vol. 18,p. 291 - 305.

8
[ 108-24-7 ]
[ 71176-54-0 ]
[ 177164-76-0 ]

References: [1]Advanced Synthesis and Catalysis,2005,vol. 347,p. 161 - 171.
[2]Journal of the American Chemical Society,1999,vol. 121,p. 9531 - 9538.
[3]Canadian Journal of Chemistry,2012,vol. 90,p. 138 - 144.
[4]Bulletin of the Chemical Society of Japan,2008,vol. 81,p. 1012 - 1018.

9
[ 71176-54-0 ]
Cu₂(CN)2 [ No CAS ]
[ 146335-23-1 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 535 - 544.

10
[ 71176-54-0 ]
[ 779345-61-8 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4350 - 4364.
[2]Organic and Biomolecular Chemistry,2004,vol. 2,p. 637 - 641.

11
[ 99-27-4 ]
[ 71176-54-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h;Reflux;	A solution of dimethyl 5-aminoisophthalate (20.0 g, 96 mmol) in THF (350 mL) was added, dropwise, to a refluxing mixture of 3.75 eq L1AIH4 (13.6 g, 358 mmol) in THF (440 mL) over one hour. The mixture was stirred at reflux for a further two hours, then cooled to room temperature and quenched by the careful addition of MeOH (27 mL) then water (40 mL). After stirring the quenched mixture for two hours it was filtered and concentrated to dryness. The residue was recrystallized (2X) from EtOAc to afford 15 as brownish-yellow crystals (10.2 g, 70 %).
70%	With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h;Reflux;	A solution of dimethyl 5-aminoisophthalate (20.0 g, 96 mmol) in THF (350 mL) was added, dropwise, to a refluxing mixture of 3.75 eq L1AIH4 (13.6 g, 358 mmol) in THF (440 mL) over one hour. The mixture was stirred at reflux for a further two hours, then cooled to room temperature and quenched by the careful addition of MeOH (27 mL) then water (40 mL). After stirring the quenched mixture for two hours it was filtered and concentrated to dryness. The residue was recrystallized (2X) from EtOAc to afford 15 as brownish-yellow crystals (10.2 g, 70 %).
70%	With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h;Reflux;	A solution of dimethyl 5-aminoisophthalate (20.0 g, 96 mmol) in THF (350 mL) was added, dropwise, to a refluxing mixture of 3.75 eq LiAlFL (13.6 g, 358 mmol) in THF (440 mL) over one hour. The mixture was stirred at reflux for a further two hours, then cooled to room temperature and quenched by the careful addition of MeOH (27 mL) then water (40 mL). After stirring the quenched mixture for two hours it was filtered and concentrated to dryness. The residue was recrystallized (2X) from EtOAc to afford 15 as brownish-yellow crystals (10.2 g, 70 %).

References: [1]Advanced Synthesis and Catalysis,2005,vol. 347,p. 161 - 171.
[2]Journal of Medicinal Chemistry,2011,vol. 54,p. 4350 - 4364.
[3]Patent: WO2017/177326,2017,A1 .Location in patent: Page/Page column 59; 64; 68.
[4]Patent: WO2018/191278,2018,A2 .Location in patent: Page/Page column 86; 90; 91; 94; 97.
[5]Patent: WO2019/51257,2019,A2 .Location in patent: Page/Page column 170-171; 177.
[6]Organic and Biomolecular Chemistry,2018,vol. 16,p. 7588 - 7594.
[7]Journal of Medicinal Chemistry,2010,vol. 53,p. 3480 - 3488.
[8]Journal of Medicinal Chemistry,2012,vol. 55,p. 10405 - 10413.
[9]Bulletin of the Chemical Society of Japan,2008,vol. 81,p. 1012 - 1018.
[10]Supramolecular Chemistry,2018,vol. 30,p. 822 - 831.
[11]Journal of the American Chemical Society,2018,vol. 140,p. 13011 - 13021.

12
[ 5413-85-4 ]
[ 71176-54-0 ]
[ 867259-33-4 ]