252061-66-8|5-Hydroxyisoindolin-1-one| Ambeed

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Quality Control of [ 252061-66-8 ] Purity: 97% SDS Specification

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Product Details of [ 252061-66-8 ]

CAS No. :	252061-66-8
Formula :	C₈H₇NO₂
M.W :	149.15
SMILES Code :	O=C1NCC2=C1C=CC(O)=C2
MDL No. :	MFCD10000830
InChI Key :	NLNNRNIJRFYGFB-UHFFFAOYSA-N
Pubchem ID :	22594207

Safety of [ 252061-66-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 252061-66-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	43.42
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	49.33 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.98
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	0.42
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.1
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.	0.52
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	1.37
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.68

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.43
Solubility	5.5 mg/ml ; 0.0369 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.	-1.02
Solubility	14.1 mg/ml ; 0.0948 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	-2.29
Solubility	0.758 mg/ml ; 0.00508 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	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.91 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)	1.12

Application In Synthesis of [ 252061-66-8 ]

* 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 [ 252061-66-8 ]

[ 252061-66-8 ] Synthesis Path-Downstream 1~25

1
[ 22246-66-8 ]
[ 252061-66-8 ]

Yield	Reaction Conditions	Operation in experiment
79%		5-Hydroxy-2,3-dihydro-isoindol-1-oneTo a suspension of 5-Methoxy-2,3-dihydro-isoindol-1-one (5.65 g, 34.6 mmol) in dichloromethane (300 mL) was added boron tribromide (25.1 g, 100 mmol, 1.0 M solution in DCM) slowly over 20 min at 0 0C. The reaction was allowed to warm to room temperature after addition (3 h). The reaction was quenched with methanol (100 mL) at 0 0C and then allowed to stir for 3 h. The solution was concentrated and 500 mL of water was added and heated to 60 0C for 1 hour. The mixture was cooled and 5-Hydroxy-2,3-dihydro-isoindol-1-one was filtered off as a solid (4.10 g, 79%, CASNo. 252061-66-8). MS: ES: M+1: 150.0 (149.0)
72%		A mixture Of 5-METHOXY-2, 3-DIHYDRO-ISOINDOL-1-ONE (3.7 g, 23 mmol) and boron tri- bromide (1 M in [CH2C12,] 15.2 mL, 88 mmol) in [CH2CI2] (30 mL) [AT-78 C] was stirred for 16 h at RT. The mixture was then cooled [TO-78 C] and [MEOH] (25 mL) was added. After lh at-78 C the mixture was evaporated and the residue purified by chromatography [(SI02,] [CH2C12] : 2N NH3-MeOH 98: 2 to 90: 10) to afford the title product (2.5 g, 72%) as an off- white solid. MS m/e = 148.0 (M-H+).

References: [1]Patent: WO2008/20306,2008,A2 .Location in patent: Page/Page column 35-36.
[2]Patent: WO2004/14856,2004,A1 .Location in patent: Page 9; 14-15.
[3]Journal of Medicinal Chemistry,2012,vol. 55,p. 3975 - 3991.
[4]Journal of Medicinal Chemistry,1999,vol. 42,p. 4875 - 4889.
[5]Chemical and Pharmaceutical Bulletin,2011,vol. 59,p. 96 - 99.

2
[ 17201-43-3 ]
[ 252061-66-8 ]
[ 252061-67-9 ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 4875 - 4889.

3
[ 109-70-6 ]
[ 252061-66-8 ]
[ 928257-25-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate; potassium iodide; In acetonitrile; for 18h;Heating / reflux;	B16: 5-(3-Chloro-propoxy)-2,3-dihydro-isoindol-1 -one To a suspension of 5-Hydroxy-2,3-dihydro-isoindol-1-one <0.78 g, 5.25 mmol) in acetonitrile (17 mL) was added 1-bromo-3-chloro-propane (2.07 g, 13.5 mmol), potassium carbonate (1.896 g, 13.7 mmol), and potassium iodide (0.27 g, 0.31 mmol). After heating at reflux for 18 h the mixture was concentrated and crystallized from acetonitrile/water to obtain 5-(3-Chloro-propoxy)-2,3-dihydro-isoindol-1-one (B16), (1.30 g, quant). MS: ES: M+1 : 226.0 (225.0).

References: [1]Patent: WO2008/20306,2008,A2 .Location in patent: Page/Page column 35-36.

4
[ 6940-78-9 ]
[ 252061-66-8 ]
[ 1007455-38-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate; potassium iodide; In acetonitrile; for 18h;Heating / reflux;	B17: 5-(4-Chloro-butoxy)-2,3-dihydro-isoindol-1 -oneTo a suspension of 5-Hydroxy-2,3-dihydro-isoindol-1-one (2.03 g, 13.6 mmol) in acetonitrile (17 mL) was added 1-bromo-4-chloro-butane (5.65 g, 32.9 mmol), potassium carbonate (4.63 g, 33.5 mmol), and potassium iodide (0.70 g, 0.31 mmol). After heating at reflux for 18 h the mixture was concentrated and crystallized from acetonitrile/water to obtain 5-(4-Chloro-butoxy)-2,3-dihydro-isoindol-1-one (B17), <3.23 g, 98 %). MS: ES: M+1 : 240.0 (239.6)

References: [1]Patent: WO2008/20306,2008,A2 .Location in patent: Page/Page column 35-36.

5
[ 252061-66-8 ]
[ 252061-69-1 ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 4875 - 4889.

6
[ 252061-66-8 ]
[ 252061-71-5 ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 4875 - 4889.

7
[ 252061-66-8 ]
[5-(4-carbamimidoyl-benzyloxy)-1-oxo-1,3-dihydro-isoindol-2-yl]-acetic acid; compound with trifluoro-acetic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 4875 - 4889.

8
[ 456-41-7 ]
[ 252061-66-8 ]
[ 659737-45-8 ]

Yield	Reaction Conditions	Operation in experiment
67%	With potassium carbonate; In acetone; for 22h;Heating / reflux;	A mixture OF 5-HYDROXY-2, 3-DIHYDRO-ISOINDOL-1-ONE (2.4 g, 16 mmol), potassium carbon- ate (2.4 g, 18 mmol) and 3-fluorobenzyl bromide (3.3 g, 18 mmol) in acetone (40 mL) was heated under reflux for 22 h. After cooling to RT the mixture was filtered and evaporated. The residue was purified by chromatography [(SI02,] [CH2C12] : 2N NH3-MeOH 90: 10) to afford the title product (2.8 g, 67%) as a white solid. MS m/e = 257.2 [(M+).]

References: [1]Patent: WO2004/14856,2004,A1 .Location in patent: Page 15.

9
[ 50727-06-5 ]
[ 252061-66-8 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; zinc; for 0.666667h;Heating / reflux;	To a solution of 5-hydroxyphthalimide (19.8 g, 121 mmol) in AcOH (500 mL) was slowly added zinc dust (47.6 g, 729 mmol) in portions, then the mixture was heated at the reflux temp. for 40 min., filtered hot, and concentrated under reduced pressure. The reaction was repeated on the same scale and the combined oily residue was purified by column chromatography (1.1 Kg SiO2; gradient from 60% EtOAc/40% hexane to 25% MeOH/75% EtOAc) to give 5-hydroxyisoindolin-1-one (3.77 g): TLC (100% EtOAc) Rf 0.17; HPLC ES-MS m/z 150 ((M+H)+).

References: [1]Patent: US2003/207872,2003,A1 .Location in patent: Page/Page column 13.

Yield	Reaction Conditions	Operation in experiment
		...he customary manner and 2-(1,3-benzodioxol-5-yl)-2-(1,3-dihydro-1,3-dioxoisoindol-5-yloxy)-N-(4-tert-butylphenylsulfonyl)acetamide, m.p. 215, is obtained; potassium salt of the compound FAB 575, m.p. 171. Analogously, by reaction of methyl benzo[1,3]dioxol-5-ylbromoacetate with ... 5-hydroxy-6-propyl-1,3-dihydroisoindole-1,3-dione 5-hydroxy-1,3-dihydro-1-isoindolone 5-hydroxyindole ...

11
[ 350-46-9 ]
[ 252061-66-8 ]
[ 284462-53-9 ]

Yield	Reaction Conditions	Operation in experiment
89%		Step 2. Synthesis of 4-(1-isoindolinon-5-yloxy)-1-nitrobenzene To a slurry of NaH (0.39 g, 16.1 mmol) in DMF at 0 C. was added <strong>[252061-66-8]5-hydroxyisoindolin-1-one</strong> (2.0 g, 13.4 mmol) in portions. The resulting slurry was allowed to warm to room temp. and was stirred for 45 min., then 4-fluoro-1-nitrobenzene was added and then mixture was heated at 70 C. for 3 h. The mixture was cooled to 0 C. and treated with water dropwise until a precipitate formed. The resulting solids were collected to give 4-(1-isoindolinon-5-yloxy)-1-nitrobenzene as a dark yellow solid (3.23 g, 89%): TLC (100% EtOAc) Rf 0.35.

References: [1]Patent: US2003/207872,2003,A1 .Location in patent: Page/Page column 13.

12
[ 1037754-61-2 ]
[ 252061-66-8 ]
[ 1204309-91-0 ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃;	To a solution of 5-hydroxy-2,3-dihydroisoindol-l-one (100 mg, 671 mumol) in THF (7 mL) and DMF (2 mL) was added 3-[l-(3-isopropyl[l,2,4]oxadiazol-5-yl)piperidin-4-yl]propan- l-ol (Preparation 3, 165 mg, 652 mumol) and PPh3 (444 mg, 1.67 mmol). The resulting reaction mixture was cooled to O0C prior to the addition of DIAD (564 muL, 2.86 mmol). The reaction mixture was stirred at ambient temperature for 1.5 h, then the solvent was removed in vacuo. The reaction mixture was diluted with EtOAc (50 mL), washed with 2M NaOH (20 mL), H2O (20 mL) and brine (20 mL), dried (MgSO4), filtered and concentrated in vacuo. Purification by column chromatography (EtOAc-IH, 3:2 to 7:3 to 1:0) afforded the title compound: RT = 3.47 min; mlz (ES+) = 385.04 [M + H]+ (Method A).

References: [1]Patent: WO2010/4347,2010,A1 .Location in patent: Page/Page column 45.

13
[ 50727-04-3 ]
[ 252061-66-8 ]