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[ CAS No. 252061-66-8 ] {[proInfo.proName]}

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Chemical Structure| 252061-66-8
Chemical Structure| 252061-66-8
Structure of 252061-66-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 252061-66-8 ]

CAS No. :252061-66-8 MDL No. :MFCD10000830
Formula : C8H7NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :NLNNRNIJRFYGFB-UHFFFAOYSA-N
M.W : 149.15 Pubchem ID :22594207
Synonyms :

Calculated chemistry of [ 252061-66-8 ]

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 : 49.33 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.98
Log Po/w (XLOGP3) : 0.42
Log Po/w (WLOGP) : 0.1
Log Po/w (MLOGP) : 0.52
Log Po/w (SILICOS-IT) : 1.37
Consensus Log Po/w : 0.68

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.43
Solubility : 5.5 mg/ml ; 0.0369 mol/l
Class : Very soluble
Log S (Ali) : -1.02
Solubility : 14.1 mg/ml ; 0.0948 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.29
Solubility : 0.758 mg/ml ; 0.00508 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.12

Safety of [ 252061-66-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

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.

  • Upstream synthesis route of [ 252061-66-8 ]
  • Downstream synthetic route of [ 252061-66-8 ]

[ 252061-66-8 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 22246-66-8 ]
  • [ 252061-66-8 ]
YieldReaction ConditionsOperation in experiment
79%
Stage #1: With boron tribromide In dichloromethane at 0 - 20℃; for 3.33333 h;
Stage #2: With methanol In dichloromethane at 0℃; for 3 h;
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, 79percent, CASNo. 252061-66-8). MS: ES: M+1: 150.0 (149.0)
72%
Stage #1: With boron tribromide In dichloromethane at -78 - 20℃; for 16 h;
Stage #2: With methanol In dichloromethane at -78℃; for 1 h;
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, 72percent) as an off- white solid. MS m/e = 148.0 (M-H+).
Reference: [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, # 8, p. 3975 - 3991
[4] Journal of Medicinal Chemistry, 1999, vol. 42, # 23, p. 4875 - 4889
[5] Chemical and Pharmaceutical Bulletin, 2011, vol. 59, # 1, p. 96 - 99
  • 2
  • [ 50727-06-5 ]
  • [ 252061-66-8 ]
Reference: [1] Patent: US2003/207872, 2003, A1, . Location in patent: Page/Page column 13
  • 3
  • [ 35598-05-1 ]
  • [ 252061-66-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 8, p. 3975 - 3991
  • 4
  • [ 15365-25-0 ]
  • [ 252061-66-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 8, p. 3975 - 3991
  • 5
  • [ 50727-04-3 ]
  • [ 252061-66-8 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2011, vol. 59, # 1, p. 96 - 99
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