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[ CAS No. 2732-18-5 ] {[proInfo.proName]}

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Chemical Structure| 2732-18-5
Chemical Structure| 2732-18-5
Structure of 2732-18-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 2732-18-5 ]

CAS No. :2732-18-5 MDL No. :MFCD00488354
Formula : C9H6O4 Boiling Point : -
Linear Structure Formula :- InChI Key :KIQQFVJHWNCGAU-UHFFFAOYSA-N
M.W : 178.14 Pubchem ID :5324654
Synonyms :
5,7-dihydroxychromen-2-one

Calculated chemistry of [ 2732-18-5 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 46.53
TPSA : 70.67 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.11
Log Po/w (XLOGP3) : 1.2
Log Po/w (WLOGP) : 1.2
Log Po/w (MLOGP) : 0.45
Log Po/w (SILICOS-IT) : 1.46
Consensus Log Po/w : 1.09

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.27
Solubility : 0.957 mg/ml ; 0.00537 mol/l
Class : Soluble
Log S (Ali) : -2.28
Solubility : 0.934 mg/ml ; 0.00524 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.46
Solubility : 0.619 mg/ml ; 0.00348 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.64

Safety of [ 2732-18-5 ]

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 [ 2732-18-5 ]

* 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.

  • Upstream synthesis route of [ 2732-18-5 ]
  • Downstream synthetic route of [ 2732-18-5 ]

[ 2732-18-5 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 108-73-6 ]
  • [ 471-25-0 ]
  • [ 2732-18-5 ]
YieldReaction ConditionsOperation in experiment
96% at 80℃; for 0.0333333 h; Microwave irradiation General procedure: An open reaction vessel containing a mixture of the phenol (1.0 mmol), propiolic acid (1.1 mmol), and Yb(OTf)3 hydrate (0.1 mmol) was put in the MW apparatus and irradiated at 200 W (80 °C) for 2 min. The reaction was monitored by TLC (eluent CH2Cl2 / MeOH 99:1). The crude solid obtained was diluted with Et2O and the resulting suspension filtered under vacuum to separate the catalyst, the precipitate washed several times with Et2O. The filtrate was washed twice with a 5percent NaHCO3 solution (10 mL) dried over MgSO4 and evaporated to dryness under vacuum yielding the desired product.
1.08 g for 12 h; Reflux A solution of phloroglucinol (1.0 g, 7.93 mmol) in H2O(15.0 mL) was treated with propiolic acid (0.59 ml,9.52 mmol), and the mixture was stirred under reflux for12 h. Removal of the solvent from the reaction mixtureunder reduced pressure furnished a residue, which waspurified by normal-phase silica gel column chromatography[CHCl3–MeOH = 10:1] to give 5,7-dihydroxycoumarin(1a, 1.08 g).1a: White powder; IR (ATR): mmax 1219, 773 cm-1;EIMS: m/z 178 [M]+; HREIMS: m/z 178.0268 (Calcd forC9H6O4 [M]+: m/z 178.0266); 1H NMR (400 MHz,methanol-d4) δ 5.93 (d, J = 9.6), 6.11 (d, J = 2.4), 6.12 (d,J = 2.4), 7.96 (d, J = 9.6).
Reference: [1] Synlett, 1999, # 5, p. 608 - 610
[2] Tetrahedron Letters, 2016, vol. 57, # 26, p. 2939 - 2942
[3] Synthesis, 2011, # 8, p. 1283 - 1289
[4] Journal of Natural Medicines, 2017, vol. 71, # 4, p. 735 - 744
  • 2
  • [ 108-73-6 ]
  • [ 623-47-2 ]
  • [ 2732-18-5 ]
Reference: [1] Journal of Natural Products, 2005, vol. 68, # 1, p. 78 - 82
[2] Synthesis, 2011, # 22, p. 3692 - 3696
[3] Chemical Biology and Drug Design, 2013, vol. 81, # 5, p. 607 - 614
[4] Tetrahedron, 2008, vol. 64, # 17, p. 3661 - 3666
[5] Asian Journal of Chemistry, 2013, vol. 25, # 7, p. 3629 - 3632
[6] Organic Letters, 2013, vol. 15, # 15, p. 3856 - 3859
[7] Journal of the American Chemical Society, 1996, vol. 118, # 26, p. 6305 - 6306
[8] Journal of the American Chemical Society, 2003, vol. 125, # 15, p. 4518 - 4526
[9] Synthesis (Germany), 2015, vol. 47, # 18, p. 2713 - 2720
[10] Journal of Medicinal Chemistry, 1998, vol. 41, # 23, p. 4542 - 4549
[11] Synthetic Communications, 2004, vol. 34, # 10, p. 1909 - 1914
  • 3
  • [ 108-73-6 ]
  • [ 922-67-8 ]
  • [ 2732-18-5 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 4, p. 934 - 937
  • 4
  • [ 108-73-6 ]
  • [ 471-25-0 ]
  • [ 2732-18-5 ]
  • [ 1447758-10-2 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 15, p. 3856 - 3859
  • 5
  • [ 487-70-7 ]
  • [ 2732-18-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1907, vol. 357, p. 373
[2] Tetrahedron Letters, 2009, vol. 50, # 33, p. 4769 - 4772
  • 6
  • [ 21524-17-4 ]
  • [ 2732-18-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1907, vol. 357, p. 373
[2] Archiv der Pharmazie (Weinheim, Germany), 1904, vol. 242, p. 294
[3] Journal of the Chemical Society, 1936, p. 1831
  • 7
  • [ 882685-19-0 ]
  • [ 2732-18-5 ]
Reference: [1] Journal of Mass Spectrometry, 2005, vol. 40, # 10, p. 1319 - 1326
  • 8
  • [ 84740-26-1 ]
  • [ 2732-18-5 ]
Reference: [1] Chemistry of Natural Compounds, 1983, vol. 19, # 4, p. 413 - 416[2] Khimiya Prirodnykh Soedinenii, 1983, vol. 19, # 4, p. 441 - 445
  • 9
  • [ 108-73-6 ]
  • [ 87-13-8 ]
  • [ 2732-18-5 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958, vol. 246, p. 1701
  • 10
  • [ 1185256-07-8 ]
  • [ 2732-18-5 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 33, p. 4769 - 4772
  • 11
  • [ 882685-19-0 ]
  • [ 2732-18-5 ]
Reference: [1] Journal of Mass Spectrometry, 2005, vol. 40, # 10, p. 1319 - 1326
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