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[ CAS No. 779-27-1 ] {[proInfo.proName]}

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Chemical Structure| 779-27-1
Chemical Structure| 779-27-1
Structure of 779-27-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 779-27-1 ]

CAS No. :779-27-1 MDL No. :MFCD00017491
Formula : C10H6O5 Boiling Point : -
Linear Structure Formula :- InChI Key :LKLWLDOUZJEHDY-UHFFFAOYSA-N
M.W :206.15 Pubchem ID :5337757
Synonyms :
3-Carboxy-7-Hydroxycoumarin

Calculated chemistry of [ 779-27-1 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 51.47
TPSA : 87.74 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) : -6.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.8
Log Po/w (XLOGP3) : 1.84
Log Po/w (WLOGP) : 1.2
Log Po/w (MLOGP) : 0.66
Log Po/w (SILICOS-IT) : 1.32
Consensus Log Po/w : 1.16

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.7
Solubility : 0.407 mg/ml ; 0.00197 mol/l
Class : Soluble
Log S (Ali) : -3.3
Solubility : 0.103 mg/ml ; 0.000498 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.42
Solubility : 0.791 mg/ml ; 0.00384 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.51

Safety of [ 779-27-1 ]

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

Application In Synthesis of [ 779-27-1 ]

* 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 [ 779-27-1 ]
  • Downstream synthetic route of [ 779-27-1 ]

[ 779-27-1 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 6093-71-6 ]
  • [ 779-27-1 ]
YieldReaction ConditionsOperation in experiment
75% With hydrogenchloride In water at 90℃; for 8 h; At a temperature of 90 ° C, compound 3 (2.00 g, 8.55 mmol) was weighed in water (20 ml), concentrated hydrochloric acid (6 ml) was added and refluxed for 8 h.The reaction solution was cooled to room temperature, filtered and washed with water to give Compound 4 (1.32 g, 6.41 mmol) as a pale red solid in 75percent yield
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1986, vol. 25, p. 638 - 639
[2] Food Chemistry, 2012, vol. 135, # 4, p. 2872 - 2878
[3] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 5, p. 502 - 506
[4] Chemical Communications, 2017, vol. 53, # 11, p. 1813 - 1816
[5] Patent: CN106279125, 2017, A, . Location in patent: Paragraph 0041; 0042
[6] Organic and Biomolecular Chemistry, 2011, vol. 9, # 9, p. 3530 - 3540
[7] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 16, p. 4922 - 4926
[8] European Journal of Medicinal Chemistry, 2013, vol. 70, p. 623 - 630
[9] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 40 - 46
[10] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2018, vol. 188, p. 659 - 665
[11] European Journal of Medicinal Chemistry, 2018, vol. 152, p. 600 - 614
[12] Cell Chemical Biology, 2018,
  • 2
  • [ 2033-24-1 ]
  • [ 95-01-2 ]
  • [ 779-27-1 ]
YieldReaction ConditionsOperation in experiment
99% With tomato juice In water at 20℃; for 0.0833333 h; Sonication; Green chemistry General procedure: 2-Hydroxybenzaldehyde (acetophenone, or benzaldehydes) (1.0 mmol) and Meldrum’s acid (1.01 mmol) were suspended in the aqueous medium (juice or waste water) (2 mL). The resulting mixture was subjected to ultrasound irradiation at room temperature for 5 min (15 min). The precipitate so formed was filtrated under vacuum. Structural assignments (NMR) was made by comparison of the recorded analytical data with those of commercially available sample or those already reported for the same compounds.2-6 The aqueous medium (juice or waste water) was recovered by filtration and re-used as such to perform further processes.
92% at 60℃; for 4 h; Schlenk technique; Green chemistry General procedure: A mixture of Meldrum’s acid (0.5 mmol) and salicylaldehydes (0.55 mmol) was placed in a 10-mL Schlenk tube, then Et3N (0.015 mmol) and 50 μL water were added. The reaction mixture was stirred at the indicated temperature for 4 h. After completion of the reaction, 3 mL aqueous ethanol was added to the mixture and vigorously stirred for a moment. The pH was adjusted to 2–3 with dilute hydrochloric acid. Finally, the precipitate was separated by filtration and washed with aqueous ethanol without further purification to afford the corresponding pure adducts.
90% for 10 h; Reflux General procedure: In a round-bottomed flask the selected salicylaldehyde (1 mmol) and Meldrum's acid (1.2 mmol) in water (2 mL) were heated at reflux under stirring for 10 h; then, the reaction mixture was cooled and filtered on Büchner funnel. The products were purified by recrystallization from methanol.
77% With ammonium acetate In water at 20℃; for 0.1 h; A suspension of 2,4-dihydroxybenzaldehyde (1.30 g, 9.5 mmol) in 21 mL of water was added Meldrum's acid (1.55 g, 10.8 mmol) and ammonium acetate (150 mg, 1.9 mmol). The suspension was stirred at room temperature for about 1 h. The precipitate formed was filtered and washed with cold water (2 x 10 mL) and vacuum drying (1.5 g, yellow-orange solid, 77percent). m.p. 260-264 °C; 1H NMR (DMSO-d6): δ 11.93 (bs, 2H, OH), 8.66 (s, 1H, =CH), 7.73 (d, 1H, Ar-H, J = 8.6 Hz ), 6.83 (dd, 1H, Ar-H, J = 8.6, 2.1 Hz), 6.72 (d, 1H, Ar-H, J = 2.1 Hz)

Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 43, p. 4795 - 4798
[2] Research on Chemical Intermediates, 2016, vol. 42, # 9, p. 7057 - 7063
[3] New Journal of Chemistry, 2018, vol. 42, # 11, p. 8831 - 8842
[4] European Journal of Medicinal Chemistry, 2014, vol. 84, p. 1 - 7
[5] Tetrahedron Letters, 2003, vol. 44, # 9, p. 1755 - 1758
[6] Central European Journal of Chemistry, 2010, vol. 8, # 2, p. 370 - 374
[7] Helvetica Chimica Acta, 2012, vol. 95, # 3, p. 455 - 460
[8] Synthetic Communications, 2008, vol. 38, # 20, p. 3508 - 3513
[9] Organic and Biomolecular Chemistry, 2012, vol. 10, # 27, p. 5258 - 5265
[10] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 23, p. 5732 - 5735
[11] Organic Letters, 2004, vol. 6, # 20, p. 3561 - 3564
[12] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 8, p. 1157 - 1160
  • 3
  • [ 2033-24-1 ]
  • [ 779-27-1 ]
YieldReaction ConditionsOperation in experiment
86% for 0.25 h; Reflux; Green chemistry General procedure: A mixture of nitrone (10 mmol) and Meldrum’sacid (10 mmol) was refluxed in ethanol (15 mL) for a given time (see Table I). The progress of reaction was monitored via thin layer chromatography. After reaction completion, the reaction mass was cooledand excess solvent was removed under vacuum. Obtained crude product was washed with cold water (5 mL × 3). The solid product was filtered and dried. For further purification, products were recrystallized from EtOH. The products were characterized by comparison of their melting points and spectral (IR,1H NMR) data with those of authentic samples (authentic samples were obtained via direct Knoevenagel reaction of aldehydes with Meldrum’s acid). The representative characterization data of products was identical with those described in the literature and as shown below.
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 8, p. 1157 - 1160
  • 4
  • [ 141-82-2 ]
  • [ 95-01-2 ]
  • [ 779-27-1 ]
Reference: [1] Oriental Journal of Chemistry, 2012, vol. 28, # 4, p. 1725 - 1728
[2] Journal of Materials Chemistry B, 2018, vol. 6, # 45, p. 7439 - 7443
[3] Journal of the American Chemical Society, 1952, vol. 74, p. 5346
  • 5
  • [ 531-81-7 ]
  • [ 779-27-1 ]
Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 36, p. 10151 - 10160
[2] Journal of the American Chemical Society, 2012, vol. 134, # 4, p. 1950 - 1953
[3] Patent: WO2013/106219, 2013, A1, . Location in patent: Paragraph 0008; 0050-0066
[4] Organic and Biomolecular Chemistry, 2014, vol. 12, # 31, p. 5936 - 5944
[5] Dalton Transactions, 2015, vol. 44, # 36, p. 16061 - 16072
[6] Chemistry - A European Journal, 2016, vol. 22, # 21, p. 7268 - 7280
[7] Dalton Transactions, 2016, vol. 45, # 32, p. 12627 - 12631
[8] Chemical Communications (Cambridge, United Kingdom), 2018, vol. 54, # 84, p. 11945 - 11948
  • 6
  • [ 95-01-2 ]
  • [ 779-27-1 ]
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 9, p. 3530 - 3540
[2] Food Chemistry, 2012, vol. 135, # 4, p. 2872 - 2878
[3] European Journal of Medicinal Chemistry, 2013, vol. 70, p. 623 - 630
[4] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 5, p. 502 - 506
[5] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 40 - 46
[6] Chemical Communications, 2017, vol. 53, # 11, p. 1813 - 1816
[7] Patent: CN106279125, 2017, A,
[8] European Journal of Medicinal Chemistry, 2018, vol. 152, p. 600 - 614
[9] Cell Chemical Biology, 2018,
  • 7
  • [ 19088-73-4 ]
  • [ 779-27-1 ]
Reference: [1] Synthesis, 2003, # 15, p. 2331 - 2334
  • 8
  • [ 330996-72-0 ]
  • [ 779-27-1 ]
Reference: [1] Synthesis, 2003, # 15, p. 2331 - 2334
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