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[ CAS No. 72913-59-8 ] {[proInfo.proName]}

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Chemical Structure| 72913-59-8
Chemical Structure| 72913-59-8
Structure of 72913-59-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 72913-59-8 ]

CAS No. :72913-59-8 MDL No. :MFCD09842504
Formula : C10H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :RUBAXSSGWHONDJ-UHFFFAOYSA-N
M.W : 160.17 Pubchem ID :11040990
Synonyms :

Calculated chemistry of [ 72913-59-8 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.1
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.3
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.93 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.98
Log Po/w (XLOGP3) : 1.9
Log Po/w (WLOGP) : 1.8
Log Po/w (MLOGP) : 1.26
Log Po/w (SILICOS-IT) : 2.34
Consensus Log Po/w : 1.85

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.33
Solubility : 0.742 mg/ml ; 0.00463 mol/l
Class : Soluble
Log S (Ali) : -2.08
Solubility : 1.35 mg/ml ; 0.00841 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.76
Solubility : 0.276 mg/ml ; 0.00172 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.35

Safety of [ 72913-59-8 ]

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

Application In Synthesis of [ 72913-59-8 ]

* 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 [ 72913-59-8 ]
  • Downstream synthetic route of [ 72913-59-8 ]

[ 72913-59-8 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 5111-70-6 ]
  • [ 72913-59-8 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 2.5 h; Reflux
Stage #2: With triethylamine In tetrachloromethane at 0℃;
General procedure: NBS (195 mg, 1.1 mmol) and AIBN (2 mg, 0.01 mmol) were added to a CCl4 solution (4 ml) of the 6-methoxyindanone (162 mg, 1 mmol). The resulting mixture was stirred at reflux temperature for 2.5 h, then cooled and filtered through Celite, which was then washed with CCl4. The filtrate was cooled to 0 °C and treated with triethylamine (0.28 mL, 2.0 mmol) overnight, then concentrated in vacuuo. Chromatography of the residue (1 : 9~1 : 4 EtOAc/hexanes) afforded 97 mg (60percent) of enone 1a as the pink oil which solidified as light red solid in refrigerator.
70% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 2.5 h; Reflux General procedure: NBS (195 mg, 1.1 mmol) and AIBN (2 mg, 0.01 mmol) were added to a CCl4 solution (4 ml) of the 6-methoxyindanone (162 mg, 1 mmol).The resulting mixture was stirred at reflux temperature for 2.5 h, then cooledand filtered through Celite, which was then washed with CCl4. The filtrate was cooled to 0 °C and treated with triethylamine (0.28 mL, 2.0 mmol)overnight, then concentrated in vacuuo. Chromatography of the residue (19~14 EtOAc/hexanes) afforded 97 mg (60percent) of enone 1a as the pink oil which solidified as light red solid in refrigerator.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 5, p. 975 - 978
[2] Tetrahedron Letters, 2015, vol. 55, # 5, p. 975 - 978
[3] Organic and Biomolecular Chemistry, 2007, vol. 5, # 16, p. 2627 - 2635
[4] Tetrahedron Asymmetry, 2003, vol. 14, # 4, p. 481 - 487
[5] Journal of Chemical Research, Miniprint, 1988, # 10, p. 2401 - 2422
[6] Journal of Organic Chemistry, 1982, vol. 47, # 2, p. 315 - 319
[7] Angewandte Chemie - International Edition, 2016, vol. 55, # 33, p. 9763 - 9767[8] Angew. Chem., 2016, vol. 128, # 33, p. 9915 - 9919,5
  • 2
  • [ 79827-91-1 ]
  • [ 72913-59-8 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1988, # 10, p. 2401 - 2422
[2] Journal of Organic Chemistry, 1982, vol. 47, # 2, p. 315 - 319
[3] Tetrahedron Asymmetry, 2003, vol. 14, # 4, p. 481 - 487
[4] Patent: US2006/25601, 2006, A1, . Location in patent: Page/Page column 7
  • 3
  • [ 51699-39-9 ]
  • [ 72913-59-8 ]
Reference: [1] Journal of Organic Chemistry, 1989, vol. 54, # 24, p. 5788 - 5804
  • 4
  • [ 123208-85-5 ]
  • [ 72913-59-8 ]
Reference: [1] Journal of Organic Chemistry, 1989, vol. 54, # 24, p. 5788 - 5804
  • 5
  • [ 591-31-1 ]
  • [ 72913-59-8 ]
Reference: [1] Journal of Organic Chemistry, 1989, vol. 54, # 24, p. 5788 - 5804
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