57830-14-5|5-Phenoxyisobenzofuran-1(3H)-one| Ambeed

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Quality Control of [ 57830-14-5 ] Purity: 95% SDS Specification

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Product Details of [ 57830-14-5 ]

CAS No. :	57830-14-5
Formula :	C₁₄H₁₀O₃
M.W :	226.23
SMILES Code :	O=C1OCC2=C1C=CC(OC3=CC=CC=C3)=C2
MDL No. :	MFCD14582822
InChI Key :	BTQCNYDOVASZJD-UHFFFAOYSA-N
Pubchem ID :	44558580

Safety of [ 57830-14-5 ]

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

Computational Chemistry of [ 57830-14-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	17
Num. arom. heavy atoms	12
Fraction Csp3	0.07
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	62.28
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.	2.45
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	2.33
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.0
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.	2.68
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	3.26
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.74

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.1
Solubility	0.179 mg/ml ; 0.000793 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.	-2.72
Solubility	0.436 mg/ml ; 0.00193 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	-4.84
Solubility	0.00325 mg/ml ; 0.0000144 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	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.	-6.03 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	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)	2.09

Application In Synthesis of [ 57830-14-5 ]

* 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 [ 57830-14-5 ]

[ 57830-14-5 ] Synthesis Path-Downstream 1~36

1
[ 67-56-1 ]
[ 57830-14-5 ]
[ 1455091-04-9 ]

Yield	Reaction Conditions	Operation in experiment
83%		<strong>[57830-14-5]5-phenoxyisobenzofuran-1(3H)-one</strong> (1.0g, 4.42mmol), xylene 10mL, benzyl triethyl ammonium chloride (300 mg, 1.32 mmol) and boron trifluoride diethyl ether (200 mg, 1.41 mmol) were added to the reaction flask, and the mixture was heated to 100 C dropwise to add thionyl chloride (5.0 g, 42.03 mmol). The reaction was carried out at 135 C for 5 hours. After the reaction was completed by thin layer chromatography, the filtrate was concentrated under reduced pressure. The filtrate was concentrated to 3 mL of methanol. The mixture was stirred at 55 C for 1 hour, then concentrated to dryness under reduced pressure. The potassium carbonate solution and the sodium chloride solution were washed and concentrated to dryness to give the title compound 2c (1.0 g, 83.0%).Used directly in the next step.
87.02 g		To a solid mixture of 5-phenoxy-3H-isobenzofuran-l-one (65.54 g, 0.29 mol), boric acid (538 mg, 8.7 mmol) and triphenylphosphine oxide (2.42 g, 8.7 mmol) was added thionyl chloride (42.3 mL). The resulting mixture was refluxed overnight. After cooled, methanol (300 mL) was slowly added to the reaction mixture. It was then refluxed for 1 h and concentrated. Residue was partitioned between EtOAc and saturated NaHC03 solution. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated to provide the title compound (87.02 g, 0.31 mol) as an oil. It was used directly to the next reaction without further purification. lH NMR in CDCI3, delta in ppm: 7.91 (d, 1 H, 8.6 Hz), 7.5-6.9 (m, 7 H), 5.06 (s, 2 H), 3.83 (s, 3 H).
		102351 A reactor was charged with toluene (24 Kg), and stirring was initiated. The reactor was then charged with <strong>[57830-14-5]5-phenoxyphthalide</strong> (56 Kg), thionyl chloride (41 Kg), trimethyl borate (1 Kg), dichlorotriphenylphosphorane (2.5 Kg), and potassium carbonate (77 Kg). The mixture was heated to reflux until reaction completion and solvent was removed leaving 2-chloromethyl-4-phenoxybenzoylchloride. Methanol was charged and the mixture was heated above 50 C until reaction completion. Solvent was removed and replaced with DMF. This solution of the product methyl 2-chloromethyl-4- phenoxybenzoic acid methyl ester in DMF was used directly in the next step (HPLC: 85%).

References: [1]Patent: CN108341777,2018,A .Location in patent: Paragraph 0199; 0200; 0203; 0204.
[2]Patent: WO2013/134660,2013,A1 .Location in patent: Paragraph 0167.
[3]Patent: WO2014/14834,2014,A1 .Location in patent: Paragraph 0235.

2
[ 64169-34-2 ]
[ 108-95-2 ]
[ 57830-14-5 ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate; acetylacetone; copper(I) bromide; In N,N-dimethyl-formamide; at 90℃;Inert atmosphere;	Add phenol (20.4g, 0.22mol) and DMF 50mL to the reaction flask and start stirring.5-Bromoisobenzofuran-1(3H)-one (34.0 g, 0.16 mmol), acetylacetone (3.2 g, 0.03 mol), cuprous bromide (3.6 g, 0.03 mol), potassium carbonate (at room temperature) 30.8g, 0.22mol), three times of nitrogen replacement, heating to 90 C, stirring reaction overnight, adding 1000 mL of purified water to the reaction solution, suction filtration, the filter cake was dissolved in 800 mL of dichloromethane, and the organic phase was washed with 800 mL of 1N hydrochloric acid solution, with purified water. 1000 mL washing, drying the organic phase, and concentrating to dryness under reduced pressure to give a yellow solid.The title compound 2b (22.5 g, 63%) was obtained.
72.22 g	With 2,2,6,6-tetramethylheptane-3,5-dione; caesium carbonate; copper(l) chloride; In 1-methyl-pyrrolidin-2-one; at 130℃; for 64h;	A mixture of 5-bromo-3H-isobenzofuran- 1 -one (75.9 g, 0.36 mol) (Sigma-Aldrich), phenol (67.1 g, 0.713 mol), CuCl (17.6 g, 0.178 mol), 2,2,6,6-tetramethyl-heptane-3,5-dione (TMHD, 7.33 mL) and cesium carbonate (232.3 g, 0.713 mol) in NMP (200 mL) was heated at 130 C for 64 h. After cooled, reaction mixture was poured into ice/2M HCl mixture (1 L). The mixture was then refluxed for 1 h. After cooled, the solid was collected, rinsed with water and dried in vacuo to provide the title compound (72.22 g, 0.32 mol). lH NMR in DMSO-d6, delta in ppm: 7.82 (dd, 1 H, J = 1.6 Hz, 7.6 Hz), 7.51-7.40 (m, 2 H), 7.3-7.1 (m, 5 H), 5.31 (s, 2 H).
	With potassium carbonate; copper(I) bromide; In N,N-dimethyl-formamide; acetylacetone; at 85℃;	j0234j A reactor was charged with DMF (68 Kg), and stirring was initiated. The reactor was then charged with phenol (51 Kg), acetylacetone (8 Kg), 5-bromophthalide (85 Kg), copper bromide (9 Kg), and potassium carbonate (77 Kg). The mixture was heated above 85 C and maintained until reactioncompletion and then cooled. Water was added. Solid was filtered and washed with water. Solid was dissolved in dichloromethane, and washed with aqueous HC1 and then with water. Solvent was removed under pressure and methanol was added. The mixture was stirred and filtered. Solid was washed with methanol and dried in an oven giving 5-phenoxyphthalide (Yield: 72%, HPLC: 99.6%).

References: [1]Patent: CN108341777,2018,A .Location in patent: Paragraph 0199-0202.
[2]Patent: WO2013/134660,2013,A1 .Location in patent: Paragraph 0166.
[3]Patent: WO2014/14834,2014,A1 .Location in patent: Paragraph 0234.

3
[ 57830-14-5 ]
[ 1455091-06-1 ]