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[ CAS No. 2316-26-9 ] {[proInfo.proName]}

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Chemical Structure| 2316-26-9
Chemical Structure| 2316-26-9
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Product Details of [ 2316-26-9 ]

CAS No. :2316-26-9 MDL No. :MFCD00004387
Formula : C11H12O4 Boiling Point : -
Linear Structure Formula :- InChI Key :HJBWJAPEBGSQPR-GQCTYLIASA-N
M.W : 208.21 Pubchem ID :717531
Synonyms :
O-Methylferulic acid;Caffeic acid dimethyl ether
Chemical Name :3,4-Dimethoxycinnamic Acid

Calculated chemistry of [ 2316-26-9 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.18
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 56.1
TPSA : 55.76 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.01
Log Po/w (XLOGP3) : 2.34
Log Po/w (WLOGP) : 1.69
Log Po/w (MLOGP) : 1.3
Log Po/w (SILICOS-IT) : 1.79
Consensus Log Po/w : 1.83

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.64
Solubility : 0.48 mg/ml ; 0.00231 mol/l
Class : Soluble
Log S (Ali) : -3.15
Solubility : 0.147 mg/ml ; 0.000707 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.12
Solubility : 1.57 mg/ml ; 0.00753 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.04

Safety of [ 2316-26-9 ]

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 [ 2316-26-9 ]

* 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 [ 2316-26-9 ]
  • Downstream synthetic route of [ 2316-26-9 ]

[ 2316-26-9 ] Synthesis Path-Upstream   1~20

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Reference: [1] Tetrahedron, 1982, vol. 38, # 22, p. 3347 - 3354
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  • 5
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YieldReaction ConditionsOperation in experiment
96% With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 100 - 110℃; for 1.25 h; General procedure: To aromatic aldehyde (500 mg, 1.0 equiv) and malonic acid (981 mg, 2.0 equiv) was added DABCO (105 mg, 2 equiv) in dimethyl formamide (5 mL) and the reaction mixture was stirred at 100-110 °C for 60-90 min. After completion of the reaction (TLC monitoring), reaction mixture was poured in water and then extracted with ethyl acetate. Crude product was recrystallized from chloroform/hexane system to provide cinnamic acids in good yield.
88%
Stage #1: at 105 - 110℃;
Stage #2: With sodium hydroxide In water at 25 - 30℃;
Stage #3: With sulfuric acid In water at 15 - 20℃;
To a solution of 1000 g (6.024 mol) of 3, 4-dimethoxybenzaldehyde in 3L pyridine, 1378.3 g (13.25 mol) of malonic acid and 100 mL of piperidine were added. The resulting mixture was stirred at 105 °C to 1 10 °C for 6 - 8 h. After completion of the reaction, the reaction mixture was cooled to 25 °C to 30 °C and slowly quenched the reaction mixture into 10 L of 5 percent sodium hydroxide solution at 25 °C to 30 °C (pH: 9- 10). The reaction mixture was washed with ethyl acetate (2 x 5 L) and the organic layer separated was washed with 2 L of 5 percent sodium hydroxide solution. The aqueous layers were combined and cooled to 15 °C to 20 °C. The aqueous layer was acidified slowly with 2.5 L of 50 percent sulphuric acid below 20 °C (pH: 1-2). After an additional 30 - 45 min stirring at 15 °C to 20 °C, the solid obtained was collected by filtration, washed with 10 L of water followed by 4 L of n-hexane. The partially dried compound was unloaded into trays and dried at 55 °C to 60 °C for 8-10 h to give 1 1 10 g of the title compound.Yield: 1 1 10 g (88 percent); 1H NMR (DMSO-d6, 300 MHz): δ 7.51 (d, 1 H), 7.30 (s, 1 H), 7.19 (d, 1 H), 6.96 (d, 1 H), 6.44 (d, 1 H), 3.79 (s, 6H); MS (ES-): 207 (M-1 ).
88.9% at 75℃; for 5 h; 100 g of a three-necked reaction flask was charged with 25 g (240 mmol)Malonic acid, 33.2 g (200 mmol)3,4-dimethoxybenzaldehyde,40 ml (496 mmol) of pyridine,2 ml (20.4 mmol) of hexahydropyridine,Heated to 75 ° C and then reflux 5h,Reaction is completed,Cooling 10min,150 ml of 3 mol / ml of ice hydrochloric acid solution was added,Place the night,Filter,The precipitate was washed with 1000 ml of water,Get white crude.The crude product was recrystallized from absolute ethanol,A mixture of 37.0 g of pure white 3,4-dimethoxyphenylacrylic acid,Yield 88.9percent.
86.5% at 85℃; for 4 h; 1. In a 100 ml three-necked flask, 6.24 g (60 mmol) of malonic acid, 8.3g (50 mmol) of 3,4-dimethoxybenzaldehyde, 10 ml (124 mmol) of pyridine and 0.5 ml (5.1 mmol) of piperidine were heated 85°C for 4h. After completion of the reaction, the solution was cooled for 10 min, 60 ml of 3 mol / ml ice hydrochloric acid solution was added, and the mixture was left to stand overnight. The precipitate was washed with 400 ml of water to give a white crude product. The crude product was recrystallized from absolute ethanol to give 9 g of white pure 3,4-dimethoxyphenylacrylic acid in a yield of 86.5percent.
71.4% for 4 h; Reflux Example 7
Preparation of 3,4-Dimethoxycinnamic acid
In a 1L round bottomed flask fitted with a magnetic stirrer and a reflux condenser, a mixture of 166 g (1 mol) of veratraldehyde and 208 g (2 mol) of malonic acid in 500 mL of pyridine and 5 mL of piperidine was refluxed for 4 h. The excess pyridine was evaporated using a rotavap and 3 L of water was added to the syrupy residue which caused the formation of a solid. The mixture was acidified with 250 mL of concentrated HCl with stirring. Filtration and washing with three 100-mL portions of water and drying in air afforded 150 g (71.4percent) of the cinnamic acid, m.p. 183-185 °C. (lit. m.p. 180-182 °C.) as shown in J. G. Stuart et al, /. Het. Chem., 24. 1589 (1987); 1H-NMR (DMSO-d6) δ 3.78 (s, 3), 3.80 (s, 3), 6.44 (d, 1), 6.96 (d, 1) 7.19 (dd, 1), 7.31 (d,l), 7.52 (d, 1).

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[2] Tetrahedron Letters, 2013, vol. 54, # 39, p. 5370 - 5373
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Reference: [1] Synthetic Communications, 2009, vol. 39, # 18, p. 3254 - 3262
[2] Journal of Enzyme Inhibition and Medicinal Chemistry, 2011, vol. 26, # 4, p. 485 - 497
[3] Chemische Berichte, 1881, vol. 14, p. 967
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[2] Synthetic Communications, 2009, vol. 39, # 18, p. 3254 - 3262
[3] Journal of the Indian Chemical Society, 2013, vol. 90, # 10, p. 1853 - 1860
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