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Chemical Structure| 1570-05-4 Chemical Structure| 1570-05-4

Structure of 1570-05-4

Chemical Structure| 1570-05-4

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CAS No.: 1570-05-4

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Product Details of [ 1570-05-4 ]

CAS No. :1570-05-4
Formula : C21H18O4
M.W : 334.37
SMILES Code : O=C(O)C1=CC=C(OCC2=CC=CC=C2)C(OCC3=CC=CC=C3)=C1
MDL No. :MFCD01861843
InChI Key :BYOKJLCIKSFPDU-UHFFFAOYSA-N
Pubchem ID :10854155

Safety of [ 1570-05-4 ]

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

Computational Chemistry of [ 1570-05-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 25
Num. arom. heavy atoms 18
Fraction Csp3 0.1
Num. rotatable bonds 7
Num. H-bond acceptors 4.0
Num. H-bond donors 1.0
Molar Refractivity 95.36
TPSA ?

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

55.76 ?2

Lipophilicity

Log Po/w (iLOGP)?

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

2.81
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

4.6
Log Po/w (WLOGP)?

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

4.24
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.

3.66
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

4.32
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.93

Water Solubility

Log S (ESOL):?

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

-4.88
Solubility 0.00439 mg/ml ; 0.0000131 mol/l
Class?

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

Moderately soluble
Log S (Ali)?

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

-5.5
Solubility 0.00107 mg/ml ; 0.00000319 mol/l
Class?

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

Moderately 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

-7.07
Solubility 0.0000287 mg/ml ; 0.0000000859 mol/l
Class?

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

Poorly 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

 Yes
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

 Yes
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

 Yes
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.

-5.07 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.

0.56

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)

 2.5

Application In Synthesis of [ 1570-05-4 ]

* 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 [ 1570-05-4 ]

[ 1570-05-4 ] Synthesis Path-Downstream   1~32

  • 1
  • [ 5447-02-9 ]
  • [ 1570-05-4 ]
  • 2
  • [ 58605-10-0 ]
  • [ 1570-05-4 ]
  • 3
  • [ 1570-05-4 ]
  • [ 1592-48-9 ]
  • 4
  • [ 1570-05-4 ]
  • [ 1486-54-0 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride;pyridine; for 4h;Heating / reflux; 3, [4-DIBENZYLOXYBENZOIC] acid (3.1 g. 9.3 mmol) was combined with pyridine (5 drops, catalytic) and thionyl chloride (15 ml, 205 [MMOL).] The solution was heated at reflux for 4 h, cooled, and excess thionyl chloride removed under reduced pressure. The crude product was dissolved in benzene (50 [ML),] and stripped of solvent under vacuum. The benzoyl chloride (theoretical yield 3.4 g) was then dissolved in dichloromethane and used directly in the next step.
With oxalyl dichloride; In dichloromethane; at 20℃; for 2h; Reference Example 1; General syntheis methods of side chain amines (a)-(n); As illustrated in the synthesis route above, an equivalent mole of oxalyl chloride was added to a methylene chloride (10 V) solution (suspension) of benzoic acid derivative (A), which corresponds to side chains (a)-(n), followed by stirring at room temperature for 2 hours. After concentration in vacuo until reaching about-half volume, the resultant was added to an amine (1.0 equivalent/Et3N (1.2 equivalent)/THF solution), which corresponds to side chains (a)-(n), that had been cooled to - 20°C, subsequently stirring for 30 minutes. Diluting with methylene chloride, washing with water, drying, and then concentrating the filtrate yielded desired amine (C) (side chains (a)-(n)) (90percent or higher yield). Physical constans of side chains (a)-(n) are shown below.Side chain (a) [Show Image] 1H-NMR (CDCl3) delta(delta): 1.72-1.88 (6H, m), 2.50-2.62 (4H, m), 2.68 (2H, t, J = 5.7 Hz), 3.52-3.57 (2H, m), 5.19 (4H, s), 6.90 (1H, d, J =8.7 Hz), 7.21-7.60 (11H, m), 7.56 (1H, d, J = 1.8 Hz), 8.49 (1H, bs). LC/MS (ES +) : 445 (M+H+)
  • 5
  • [ 1570-05-4 ]
  • 3,4-bis-benzyloxy-benzoic acid-(2-[2]furyl-ethylamide) [ No CAS ]
  • 6
  • [ 99-50-3 ]
  • [ 100-44-7 ]
  • [ 1570-05-4 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In ethanol; (1) To a suspension of 3,4-dihydroxybenzoic acid (25.4 g, 0.17 mle) in ethanol (250 ml), 5N NaOH aq. (270 ml) and benzyl chloride (102 g, 0.81 mole) were added. The resulting mixture was reacted with stirring for 6 hours under reflux. The reaction mixture was cooled to room temperature, allowed to stand at same temperature overnight and acidified with conc. hydrochloric acid (40 ml). The precipitate was filtered, washed with hot ethanol and dried under reduced pressure to give 38.2 g of 3,4-dibenzyloxybenzoic acid as pale yellow crystals having a m.p. of 184°-186° C. 1 H-NMR delta ppm (DMSO-d6): 3.38 (1H, bs, OH), 5.18 and5.22 (each 2H, each s, each ARCH2 O-), 7.16(1H, d, J=8.8Hz, Ar 5-H), 7.30 - 7.57 (12H,m, ArH). IR (KBr-disk) nu cm-1: 1679 (C=O).
With sodium hydroxide; In ethanol; (1) To a suspension of 3,4-dihydroxybenzoic acid (25.4 g, 0.17 mole) in ethanol (250 ml), 5N NaOH aq. (270 ml) and benzyl chloride (102 g, 0.81 mole) were added, and the mixture was reacted with stirring for 6 hours under reflux. The reaction mixture was cooled to room temperature, allowed to stand at same temperature overnight and acidified with conc. hydrochloric acid (40 ml). The precipitate was filtered, washed with hot ethanol and dried under reduced pressure to give 38.2 g of 3,4-dibenzyloxybenzoic acid as pale yellow crystals having a m.p. of 184-186°C.
  • 7
  • [ 544-16-1 ]
  • [ 17269-65-7 ]
  • [ 141-52-6 ]
  • [ 71-43-2 ]
  • [ 1570-05-4 ]
  • 8
  • [ 544-16-1 ]
  • [ 27628-06-4 ]
  • [ 141-52-6 ]
  • [ 71-43-2 ]
  • [ 1570-05-4 ]
  • 9
  • [ 1570-05-4 ]
  • [ 69788-95-0 ]
  • [ 765848-22-4 ]
  • 10
  • [ 6066-82-6 ]
  • [ 1570-05-4 ]
  • [ 123198-00-5 ]
  • 11
  • [ 1570-05-4 ]
  • [ 95946-91-1 ]
  • 12
  • [ 1570-05-4 ]
  • [ 109-89-7 ]
  • [ 95822-16-5 ]
  • 13
  • [ 54544-05-7 ]
  • [ 1570-05-4 ]
YieldReaction ConditionsOperation in experiment
74% With sodium hydroxide; water; In methanol; for 4h;Heating / reflux; C) 3, 4-Dibenzyloxy benzoic acid; A solution of sodium hydroxide (1.2 g) in methanol (100 ml) was added to a solution of 3,4-dibenzyloxy benzoic acid methyl ester (4.64 g) in methanol (50 ml) and refluxed for 4 hrs. After removal of methanol under reduced pressure the residue was dissolved in water (100 ml) and washed with ethyl acetate (2 x 50 ml). The aqueous layer was acidified with 2N hydrochloric acid to pH 2. The precipitated product was collected by filtration which on drying under vacuum provided 2.4 g of 3,4-benzyloxy benzoic acid. (Yield = 74%) 'H NMR CDC13 7.7 (2H, b, s) 7.27-7.5 (10H, m) 6.98 (lH, d, J 8Hz) 5.26 (2H, s) 5.22 (2H, s)
32.2 g With sodium hydroxide; In tetrahydrofuran; methanol; water; at 80℃; for 1h; To a solution of 8b (15.0 g, 97.4 mmol) in MeOH (360 mL) was added SOCl2 (7.9 mL, 48.7 mmol) fordropwise at 60 C. The reaction mixture was stirred at 60 C for 10 h. Then, the reaction mixture wasevaporated under reduced pressure. The crude mixture was applied to following reaction without furtherpurification.To a mixture of crude residue and K2CO3 (40.4 g, 0.292 mol) in DMF (162 mL) was added benzylbromide (29.0 mL, 0.244 mol) at 100 C. The reaction mixture was stirred at 100 C for 16 h. Then, thereaction mixture was filtered through a pad of Celite, diluted with H2O, and extracted with EtOAc. Theorganic layer was washed with water and brine, dried over anhydrous MgSO4, and evaporated underreduced pressure. The crude mixture was applied to following reaction without further purification.To a stirred solution of crude residue in MeOH/THF (1/1, 324 mL) were added 4 M NaOH aq. (85 mL,0.34 mol) at 80 C. The reaction mixture was stirred at same temperature for 1 h. Then, the reactionmixture was quenched with 6 M HCl aq., filtered and washed with H2O to give 9b (32.2 g, 96.3 mmol,99%) as a white solid.Spectral data for 9b were in good agreement with those reported in reference.16
With sodium chlorite; sodium hydrogenphosphate dodecahydrate; dihydrogen peroxide; In water; acetonitrile; at 20℃; for 2h; General procedure: The compound 2a (4.7 mmol) was dissolved in the mixed solvent (MeCN/H2O, 5:1, V/V), added NaClO2 (687.0 mg), NaH2PO4.12H2O (883.8 mg) and H2O2 (3.0 mL), then the reaction mixture was stirred for 2 h at room temperature. After completion of the reaction, the solution was acidified with 1 mol/L HCl, extracted with ethyl acetate, and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure to provide the yellow residue, which was used directly in the next step without purification and structural characterization.
  • 14
  • [ 1570-05-4 ]
  • [ 1486-54-0 ]
  • [ 1592-48-9 ]
  • 15
  • [ 5447-02-9 ]
  • [ 1570-05-4 ]
  • [ 189082-97-1 ]
  • 18
  • 1-<3.4-dibenzyloxy-phenyl>-ethanone-(1) [ No CAS ]
  • [ 1570-05-4 ]
  • 19
  • 1-<3.4-dibenzyloxy-phenyl>-propanone-(1) [ No CAS ]
  • [ 1570-05-4 ]
  • 20
  • [ 1570-05-4 ]
  • 2-[2-(2-amino-acetylamino)-acetylamino]-3-(1-trityl-1<i>H</i>-imidazol-4-yl)-propionic acid methyl ester [ No CAS ]
  • [ 295804-11-4 ]
  • 21
  • [ 13157-90-9 ]
  • [ 13157-89-6 ]
  • [ 1570-05-4 ]
  • 22
  • [ 1570-05-4 ]
  • 5,7-bis(benzyloxy)chroman-3-ol [ No CAS ]
  • 3,4-bis-benzyloxy-benzoic acid 5,7-bis-benzyloxy-chroman-3-yl ester [ No CAS ]
  • 23
  • [ 174398-83-5 ]
  • [ 1570-05-4 ]
YieldReaction ConditionsOperation in experiment
With water; sodium hydroxide; In ethanol; at 60℃; for 2h; (Second step) Stirrer,And a reaction vessel equipped with a thermometer,20 g (55 mmol) of the compound represented by formula (S-1),Sodium hydroxide 5.3 g (132 mmol), ethanol 200 ml,Add 50 ml of pure water,Hydrolysis was performed by stirring at 60 C. for 2 hours.After the reaction is completeA 10% aqueous hydrochloric acid solution was added to neutralize the reaction solution.After cooling the reaction solution, the precipitated crystals are filtered,The crystals were washed with water and ethanol and dried.Further, 18 g (53 mmol) of 3,4-dibenzyloxybenzoic acid obtained was added to a stirrer,Charge into a reaction vessel equipped with a cooler and thermometer,Furthermore, 3.7 g (27 mmol) of 2- (4-hydroxyphenyl) ethanol,610 mg of dimethylaminopyridine,200 ml of methylene chloride was charged.Keep the reaction vessel at 5 C or below with an ice-cooled bath.In an atmosphere of nitrogen gas, 8 g (63 mmol) of diisopropylcarbodiimide was slowly added dropwise. After completion of dropping, the reaction vessel was returned to room temperature and reacted for 5 hours. After the reaction solution was filtered, 200 ml of methylene chloride was added to the filtrate, washed with a 10% aqueous hydrochloric acid solution, further washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified with a double amount (weight ratio) silica gel column and recrystallized with methylene chloride / methanol to obtain 17.7 g of a compound represented by the formula (S-3).
  • 24
  • [ 882427-72-7 ]
  • [ 1570-05-4 ]
YieldReaction ConditionsOperation in experiment
2.81 g General procedure: A solution of hydroxy benzoic acid (1.0 equiv), BnBr (3-5 equiv) and K2CO3 (10-15 equiv) in DMF was stirred overnight under argon. After filtration, the solution was concentrated in vacuo to afford the crude product. The crude product was dissolved in methanol and an aqueous solution of NaOH (75 equiv) was added. The mixture was stirred at room temperature overnight and the solution concentrated in vacuo to remove the methanol. The residue was acidified with 10 percent HCl to pH 2 and then partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by recrystallization from CH2CH2 / MeOH.
With water; potassium hydroxide; In ethanol; at 20 - 70℃; Take 1.5g (3.53mmol) compound 16a in 50mL round bottom flask, was added 20mL of ethanol, taking 1g (17.85mmol) of potassium hydroxide was dissolved in 10mL of water and slowly added to the flask and the reaction stirred until the reaction mixture was homogeneous at 70 status.The reaction mixture was evaporated to an excess of ethanol, add 100mL water, cooled to room temperature.4mol·L-1 was added dropwise to acidified till no white precipitate (pH3 ~ 4), filtered, washed with water, suction filtered and dried to give a white solid.
  • 25
  • [ 882427-70-5 ]
  • [ 1570-05-4 ]
  • [ 882427-73-8 ]
  • 26
  • [ 492-62-6 ]
  • [ 1570-05-4 ]
  • β-D-glucopyranose-1,2,3,4,6-pentakis[3,4-bis(phenylmethoxy)benzoate] [ No CAS ]
  • α-D-glucopyranose-1,2,3,4,6-pentakis[3,4-bis(phenylmethoxy)benzoate] [ No CAS ]
  • 27
  • [ 1570-05-4 ]
  • [ 98-59-9 ]
  • C28H24O6S [ No CAS ]
  • 28
  • [ 1570-05-4 ]
  • [ 100-79-8 ]
  • 3,4-bis-benzyloxy-benzoic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester [ No CAS ]
  • 29
  • [ 699-83-2 ]
  • [ 1570-05-4 ]
  • [ 951321-34-9 ]
  • 30
  • [ 480-66-0 ]
  • [ 1570-05-4 ]
  • [ 951321-36-1 ]
  • 31
  • [ 480-66-0 ]
  • [ 1570-05-4 ]
  • [ 951321-36-1 ]
  • 2',4'-di(3,4-dibenzyloxybenzoyloxy)-6'-hydroxyacetophenone [ No CAS ]
 

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