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Chemical Structure| 4940-39-0
Chemical Structure| 4940-39-0
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Product Details of [ 4940-39-0 ]

CAS No. :4940-39-0 MDL No. :MFCD00006838
Formula : C10H6O4 Boiling Point : -
Linear Structure Formula :- InChI Key :RVMGXWBCQGAWBR-UHFFFAOYSA-N
M.W : 190.15 Pubchem ID :2741
Synonyms :
Chromone-2-carboxylic acid

Calculated chemistry of [ 4940-39-0 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.44
TPSA : 67.51 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) : -6.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.3
Log Po/w (XLOGP3) : 1.63
Log Po/w (WLOGP) : 1.49
Log Po/w (MLOGP) : 0.41
Log Po/w (SILICOS-IT) : 1.81
Consensus Log Po/w : 1.33

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.51
Solubility : 0.59 mg/ml ; 0.0031 mol/l
Class : Soluble
Log S (Ali) : -2.66
Solubility : 0.416 mg/ml ; 0.00219 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.99
Solubility : 0.196 mg/ml ; 0.00103 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.5

Safety of [ 4940-39-0 ]

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 [ 4940-39-0 ]

* 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 [ 4940-39-0 ]
  • Downstream synthetic route of [ 4940-39-0 ]

[ 4940-39-0 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 4940-39-0 ]
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Reference: [1] Chemistry Letters, 1999, # 9, p. 985 - 986
  • 2
  • [ 118-93-4 ]
  • [ 95-92-1 ]
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YieldReaction ConditionsOperation in experiment
83% With hydrogenchloride; sodium ethanolate In diethyl ether; ethanol; water; acetic acid EXAMPLE 8
4-Oxo4H-chromene-2-carboxylic acid
A mixture of diethyl oxalate (110 mL, 810 mmol) and 2'-hydroxyacetophenone (44 mL, 365 mmol) was added over 20 minutes to a solution of sodium ethoxide (76 g, 1.11 mol) in ethanol (600 mL).
The mixture was heated to 80° C. for one hour then cooled to room temperature.
Water (500 mL) and diethyl ether (600 mL) were added, and the mixture acidified to pH=2 with concentrated HCl.
The organic phase was separated and the aqueous phase further extracted with diethyl ether (2*).
The combined organic phase was washed with saturated aqueous sodium chloride solution (2*), dried (MgSO4), and concentrated to give an oily brown solid.
The solid was mixed with glacial acetic acid (440 mL) and concentrated HCl (110 mL) and heated to 85° C. overnight.
The mixture was cooled to room temperature, diluted with water (550 mL), and filtered.
The solids were washed with water (2*125 mL) and dried in a vacuum oven to give a purple solid (58 g, 83percent).
Mp 260-261° C.; 1H NMR (300 MHz, DMSO-d6) δ8.03 (m, 1H), 7.85 (m, 1H), 7.71 (m, 1H), 7.51 (m, 1H), 6.89 (s, 1H).
83% With hydrogenchloride; sodium ethanolate In diethyl ether; ethanol; water; acetic acid EXAMPLE 19 STR41 4-Oxo-4H-chromene-2-carboxylic acid
A mixture of diethyl oxalate (110 mL, 810 mmol) and 2'-hydroxyacetophenone (44 mL, 365 mmol) was added over 20 minutes to a solution of sodium ethoxide (76 g, 1.11 mol) in ethanol (600 mL).
The mixture was heated to 80° C. for one hour then cooled to room temperature.
Water (500 mL) and diethyl ether (600 mL) were added, and the mixture acidified to pH=2 with concentrated hydrochloric acid.
The organic phase was separated and the aqueous phase further extracted with diethyl ether (2*).
The combined organic phase was washed with saturated aqueous sodium chloride solution (2*), dried (MgSO4), and concentrated to give an oily brown solid.
The solid was mixed with glacial acetic acid (440 mL) and concentrated HCl (110 mL) and heated to 85° C. overnight.
The mixture was cooled to room temperature, diluted with water (550 mL), and filtered.
The solids were washed with water (2*125 mL) and dried in a vacuum oven to give a purple solid (58 g, 83percent).
Mp 260-261° C.; 1 H NMR (DMSO-d6, 300 MHz) δ 8.03 (m, 1 H), 7.85 (m, 1 H), 7.71 (m, 1 H), 7.51 (m, 1 H), 6.89 (s, 1 H).
Reference: [1] Patent: US6469031, 2002, B1,
[2] Patent: US6051586, 2000, A,
[3] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 1026,1029; engl. Ausg. S. 1004, 1006
[4] Helvetica Chimica Acta, 1951, vol. 34, p. 767,774
[5] Chimica Therapeutica, 1968, vol. 3, p. 270 - 273
[6] Journal of Heterocyclic Chemistry, 2010, vol. 47, # 3, p. 582 - 588
  • 3
  • [ 60-29-7 ]
  • [ 118-93-4 ]
  • [ 95-92-1 ]
  • [ 4940-39-0 ]
YieldReaction ConditionsOperation in experiment
83.5% With hydrogenchloride; sodium ethanolate; sodium In acetic acid-concentrated hydrochloric acid; ethanol; water REFERENCE EXAMPLE 1
2'-hydroxyacetophenone (25.7 g) and diethyl oxalate (33.1 g) were added to a solution of sodium ethoxide in ethanol (prepared from 13.0 g of sodium and 375 ml of ethanol), and the mixture was heated for 1 hour while refluxing.
After the reaction mixture was cooled to room temperature, ethyl ether (500 ml) was added, and the separating crystals were collected by filtration.
To this crystal, 2N hydrochloric acid (600 ml) was added, followed by ethyl ether extraction.
The ethyl ether layer was washed with water and dried (MgSO4), after which it was concentrated under reduced pressure.
The residual oily substance was dissolved in acetic acid-concentrated hydrochloric acid (1:1,200 ml) and heated for 1 hour while refluxing.
The reaction mixture was poured over water (1 liter); the separated crystals were collected by filtration and then washed by sequential additions of water, ethanol and ethyl ether in that order, to yield 4-oxo-4H-1-benzopyran-2-carboxylic acid (83.5percent), which was then recrystallized from ethanol to yield colorless needles having a melting point of 240° to 241° C. (decomposed).
Reference: [1] Patent: US5580863, 1996, A,
  • 4
  • [ 7647-01-0 ]
  • [ 118-93-4 ]
  • [ 95-92-1 ]
  • [ 4940-39-0 ]
YieldReaction ConditionsOperation in experiment
83% With sodium ethanolate In diethyl ether; ethanol; water; acetic acid EXAMPLE 8
4-Oxo-4H-chromene-2-carboxylic acid
A mixture of diethyl oxalate (110 mL, 810 mmol) and 2'-hydroxyacetophenone (44 mL, 365 mmol) was added over 20 minutes to a solution of sodium ethoxide (76 g, 1.11 mol) in ethanol (600 mL).
The mixture was heated to 80°C for one hour then cooled to room temperature.
Water (500 mL) and diethyl ether (600 mL) were added, and the mixture acidified to pH = 2 with concentrated HCI.
The organic phase was separated and the aqueous phase further extracted with diethyl ether (2x).
The combined organic phase was washed with saturated aqueous sodium chloride solution (2x), dried (MgSO4), and concentrated to give an oily brown solid.
The solid was mixed with glacial acetic acid (440 mL) and concentrated HCI (110 mL) and heated to 85°C overnight.
The mixture was cooled to room temperature, diluted with water (550 mL), and filtered.
The solids were washed with water (2 x 125 mL) and dried in a vacuum oven to give a purple solid (58 g, 83percent).
Mp 260-261 °C; 1H NMR (300 MHz, DMSO-d6) δ 8.03 (m, 1 H), 7.85 (m, 1 H), 7.71 (m, 1 H), 7.51 (m, 1 H), 6.89 (s, 1 H).
Reference: [1] Patent: EP1040106, 2002, B1,
  • 5
  • [ 14736-31-3 ]
  • [ 4940-39-0 ]
Reference: [1] Patent: EP1054881, 2008, B1, . Location in patent: Page/Page column 31
[2] Chinese Chemical Letters, 2018, vol. 29, # 6, p. 911 - 914
  • 6
  • [ 80253-60-7 ]
  • [ 4940-39-0 ]
  • [ 80253-62-9 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 2552 - 2556
  • 7
  • [ 118-93-4 ]
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Reference: [1] Helvetica Chimica Acta, 1952, vol. 35, p. 1168,1175
[2] Chinese Chemical Letters, 2018, vol. 29, # 6, p. 911 - 914
  • 8
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Reference: [1] Helvetica Chimica Acta, 1952, vol. 35, p. 1168,1175
  • 9
  • [ 5751-48-4 ]
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Reference: [1] Helvetica Chimica Acta, 1952, vol. 35, p. 1168,1175
  • 10
  • [ 65160-21-6 ]
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Reference: [1] Helvetica Chimica Acta, 1952, vol. 35, p. 1168,1175
  • 11
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Reference: [1] Helvetica Chimica Acta, 1952, vol. 35, p. 1168,1175
  • 12
  • [ 881-15-2 ]
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Reference: [1] Helvetica Chimica Acta, 1952, vol. 35, p. 1168,1175
  • 13
  • [ 157953-42-9 ]
  • [ 4940-39-0 ]
Reference: [1] Helvetica Chimica Acta, 1952, vol. 35, p. 1168,1175
  • 14
  • [ 80352-46-1 ]
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Reference: [1] Helvetica Chimica Acta, 1952, vol. 35, p. 1168,1175
  • 15
  • [ 14736-30-2 ]
  • [ 65844-02-2 ]
  • [ 4940-39-0 ]
Reference: [1] Helvetica Chimica Acta, 1952, vol. 35, p. 1168,1175
  • 16
  • [ 80856-25-3 ]
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  • [ 77488-06-3 ]
Reference: [1] Helvetica Chimica Acta, 1952, vol. 35, p. 1168,1175
  • 17
  • [ 879878-53-2 ]
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Reference: [1] Journal of the Chemical Society, 1900, vol. 77, p. 1183
  • 18
  • [ 139-02-6 ]
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Reference: [1] Chemische Berichte, 1933, vol. 66, p. 1168,1175
  • 19
  • [ 879878-53-2 ]
  • [ 75-36-5 ]
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Reference: [1] Chemische Berichte, 1933, vol. 66, p. 1168,1175
  • 20
  • [ 145430-60-0 ]
  • [ 4940-39-0 ]
  • [ 145430-62-2 ]
Reference: [1] Phosphorus, Sulfur and Silicon and the Related Elements, 1992, vol. 70, # 1/2, p. 29 - 38
  • 21
  • [ 4940-39-0 ]
  • [ 51939-71-0 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: With hydrogen; acetic acid In ethyl acetate for 22.5 h;
Stage #2: With water; sodium hydrogencarbonate In ethyl acetate
EXAMPLE 20
(+-)-Chroman-2-carboxylic acid
A mixture of the compound from Example 19 (20.0 g, 105 mmol), and palladium on activated carbon (Pd 10percent, 2.0 g) in acetic acid (200 mL) was placed under hydrogen pressure (60 psig) in a Parr hydrogenation apparatus.
After 22.5 hours the mixture was removed from the hydrogen atmosphere and filtered through a pad of Celite. The Celite pad was washed with ethyl acetate (800 mL), and the combined filtrate concentrated to give a brown oil.
The oil was dissolved in ethyl acetate (500 mL) and extracted with saturated aqueous NaHCO3 solution (4 x 125 mL).
The aqueous phase was acidified to pH = 2 with concentrated HCl and extracted with ethyl acetate (4 x 100 mL).
The combined organic phase was washed with saturated aqueous sodium chloride solution (100 mL), dried (MgSO4), and concentrated to give a colorless solid (18.0 g, 96percent).
Mp 97.5-99°C; 1H NMR (DMSO-d6, 300 MHz) δ 12.96 (br s, 1 H), 7.03 (m, 2 H), 6.78 (m, 2 H), 4.74 (dd, J = 6.4 Hz, 3.9 Hz, 1 H), 2.73 (m, 1 H), 2.63 (m, 1 H), 2.03 (m, 2 H).
95% With palladium 10% on activated carbon; hydrogen In methanol; water at 20℃; for 2 h; Inert atmosphere Intermediate- 1 Chromane -2-carboxylic acid To a suspension of commercially available chromone-2-carboxylic acid (50g, 281mmol) in methanol (500mL), slurry of (10percent Pd/C wet, 5g) in water (lOmL) was added under nitrogen atmosphere. The mixture was hydrogenated at 60 psi at room temperature (RT) and further maintained hydrogen reservoir up to 60 psi for 2h. The progress of reaction was monitored by TLC. Reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure to yield chromane -2-carboxylic acid as off-white solid (44.7 g, 95percent). m/z-178.02.
95% With palladium 10% on activated carbon; hydrogen In methanol; water at 20℃; for 2 h; Inert atmosphere Intermediate-1 Chromane-2-carboxylic Acid [0355] chromone-2-carboxylic acid (50 g, 281 mmol) in methanol (500 mL), slurry of (10percent Pd/C wet, 5 g) in water (10 mL) was added under nitrogen atmosphere. The mixture was hydrogenated at 60 psi at room temperature (RT) and further maintained hydrogen reservoir up to 60 psi for 2 h. The progress of reaction was monitored by TLC. Reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure to yield chromane-2-carboxylic acid as off-white solid (44.7 g, 95percent). m/z-178.02.
80% at 20℃; for 16 h; 4-Oxo-4H-chromene-2-carboxylic acid (4.0 g, 21.03 mmol) was dissolved in 20 mL of acetic acid. 10percent Pd/C(0.4 g) was added thereto and stirred at room temperature for 16 hours under 60 psi of hydrogen. The reaction solutionwas filtered through Celite, diluted with EtOAc, and extracted with sodium bicarbonate aqueous solution. The water layerwas again acidified with 6N HCl and extracted with EtOAc. The organic layer was dried with MgSO4 and concentratedunder reduced pressure to obtain the title compound (3.0 g, 80 percent).1H-NMR (CDCl3) δ 7.13 (1H, t), 7.05 (1H, d), 6.95∼6.85 (2H, m), 4.75 (1H, m), 3.00∼2.80 (2H, m), 2.40 (1H, m), 2.20 (1H, m)

Reference: [1] Patent: EP1054881, 2008, B1, . Location in patent: Page/Page column 31
[2] Patent: US6469031, 2002, B1,
[3] Patent: WO2013/124828, 2013, A1, . Location in patent: Page/Page column 48
[4] Patent: US2015/38546, 2015, A1, . Location in patent: Paragraph 0355-0356
[5] Patent: EP3239143, 2017, A2, . Location in patent: Paragraph 0071
[6] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1981, vol. 20, # 12, p. 1063 - 1067
[7] European Journal of Medicinal Chemistry, 1987, vol. 22, p. 539 - 544
[8] Patent: US2008/153871, 2008, A1, . Location in patent: Page/Page column 20
[9] Journal of Heterocyclic Chemistry, 2010, vol. 47, # 3, p. 582 - 588
[10] Patent: US2015/111885, 2015, A1, . Location in patent: Paragraph 1476; 1477
[11] Patent: WO2007/123941, 2007, A2, . Location in patent: Page/Page column 70
[12] Patent: WO2007/123941, 2007, A2,
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