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Chemical Structure| 609-09-6
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Product Details of [ 609-09-6 ]

CAS No. :609-09-6 MDL No. :MFCD00009121
Formula : C7H10O5 Boiling Point : -
Linear Structure Formula :- InChI Key :DBKKFIIYQGGHJO-UHFFFAOYSA-N
M.W : 174.15 Pubchem ID :69105
Synonyms :
Chemical Name :Diethyl 2-oxomalonate

Calculated chemistry of [ 609-09-6 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.57
Num. rotatable bonds : 6
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.53
TPSA : 69.67 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) : -7.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.85
Log Po/w (XLOGP3) : 0.44
Log Po/w (WLOGP) : -0.32
Log Po/w (MLOGP) : -0.33
Log Po/w (SILICOS-IT) : 0.41
Consensus Log Po/w : 0.41

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.8
Solubility : 27.5 mg/ml ; 0.158 mol/l
Class : Very soluble
Log S (Ali) : -1.47
Solubility : 5.89 mg/ml ; 0.0338 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.79
Solubility : 28.4 mg/ml ; 0.163 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.72

Safety of [ 609-09-6 ]

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 [ 609-09-6 ]

* 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 [ 609-09-6 ]
  • Downstream synthetic route of [ 609-09-6 ]

[ 609-09-6 ] Synthesis Path-Upstream   1~32

  • 1
  • [ 609-09-6 ]
  • [ 49679-45-0 ]
Reference: [1] Journal of the Indian Chemical Society, 1986, vol. 63, p. 427 - 429
[2] Journal of the Chemical Society, 1945, p. 622,625
[3] European Journal of Medicinal Chemistry, 2018, vol. 154, p. 101 - 109
  • 2
  • [ 95-54-5 ]
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  • [ 49679-45-0 ]
Reference: [1] Archiv der Pharmazie, 2012, vol. 345, # 9, p. 687 - 694
  • 3
  • [ 452-58-4 ]
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  • [ 114983-15-2 ]
  • [ 114097-17-5 ]
Reference: [1] Journal of the Chemical Society, 1957, p. 430,434
  • 4
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YieldReaction ConditionsOperation in experiment
82% With formaldehyd; ozone In methanol EXAMPLE 7
diethyl mesoxalate
258 g of diethyl methylenemalonate, prepared by a Knoevenagel condensation of malonic ester and formaldehyde, are dissolved in 1 liter of methanol and reacted with ozone, and subsequently hydrogenated, analogously to the procedure indicated in Example 5.
5 g of 10percent Pd-on-C in 200 ml of methanol are initially taken as the hydrogenation catalyst.
The consumption of hydrogen is 28.9 standard liters (86percent of theory).
Working up as in Example 5 and rectification in vacuo gives 214 g of diethyl mesoxalate boiling at 110°-112° C./20, corresponding to a yield of 82percent of theory.
Reference: [1] Patent: US4769464, 1988, A,
[2] Tetrahedron Letters, 1981, vol. 22, # 46, p. 4607 - 4610
  • 5
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YieldReaction ConditionsOperation in experiment
76% With hydrogenchloride; sodium chlorate; dihydrogen peroxide; sodium hydroxide In water at 10 - 35℃; (Reaction at pH 5 to 8) (1) In 100 g of water, 30 g (0.187 mol) of diethylmalonate was suspended, the pH was adjusted to 10 with a few drops of a 5percent aqueous solution of sodium hydroxide and the liquid temperature was set to 10° C. (2) In another reactor, 45percent aqueous solution of sodium chlorate (402 g), 35percent hydrochloric acid (100 mL), and 35percent hydrogen peroxide (84 mL) were added while keep-ing at 35° C., and bubbling was performed by introducing air into the reactor so as to generate chlorine dioxide gas having a concentration of 8 vol percent and a purity of 99percent. (3) The introduction of chlorine dioxide gas generated in (2) above into the reactor of (1) above containing suspended diethyl malonate was started via an inlet tube, and the chlorine dioxide gas was blown into the reactor over 5 hours at from 13° C. to 18° C. while maintaining the pH at from 5 to 8 by the appropriate dropwise addition of the 5percent aqueous solution of sodium hydroxide. The amount ofthe 5percent aqueous solution of sodium hydroxide used was 180 g. (4) An aqueous solution of sodium thiosulfate was added to the homogeneous solution afier the completion of the reaction to reduce residual chlorine dioxide, and the extraction was performed with ethyl acetate. Ethyl acetate was distilled off from the extract by means of a rotary evaporator, and toluene was added to the residual oil obtained and dehydration was performed under reflux. Toluene was distilled off so as to obtain 28.9 g of diethyl ketomalonate (di- ethyl mesoxalate) as the desired product. The purity determined by gas chromatography was 99.7percent and the yield was89percent.10217] Diethyl ketomalonate (diethyl mesoxalate); ‘H NMR (300 MHz, CDC13) ö ppm: 4.39 (q, J6.0 Hz, 2H), 1.36 (t, J=6.0 Hz, 3H). ‘3C NMR (300 MHz, CDC13) ö ppm: 178.2, 160.2,63.5, 13.9. GC-MS (El) mlz: 174 [M].
76% With chlorine dioxide; sodium hydroxide In water at 10 - 18℃; for 5 h; The 30g (0.187mol) malonic acid diethyla ester aerosol in 100g water, to several drops of 5percent sodium hydroxide aqueous solution to regulate pH to 10, and become liquid 10 °C the rear, with the embodiment 1 also, blown to 8vol percent of the chlorine dioxide gas, into and through the appropriate 5percent aqueous sodium hydroxide solution in order to maintain the pH 10 at the same time in the vicinity of, the 13 °C -18 ° C temperature, lasted 5 hours blown into the chlorine dioxide gas. The use of 5percent aqueous sodium hydroxide solution to 180 g. After the reaction is finished, and the implementation example 1 reaction mixed solution treated in the same way, the target keto third acid di ethyl ester (diethyl oxalate in) 28.1 g. Gas chromatographic the measured purity is 88.1percent, the yield is 76percent. As an impurity containing a large amount of the 2,2- two chlorine third b acid diethyl ester. 2,2-diacid diethyla the ester is maletwo chlorine third known compound, the technical personnel in this field identifying the known method.
Reference: [1] Patent: US2016/194268, 2016, A1, . Location in patent: Paragraph 0221; 0222; 0223; 0224; 0225; 0226; 0227-0229
[2] Patent: CN105377803, 2016, A, . Location in patent: Paragraph 0246; 0247; 0248; 0249; 0250; 0251; 0252-0260
  • 6
  • [ 105-53-3 ]
  • [ 609-09-6 ]
YieldReaction ConditionsOperation in experiment
89% With hydrogenchloride; sodium chlorate; dihydrogen peroxide; sodium hydroxide In water at 10 - 35℃; (Reaction at pH 5 to 8) (1) In 100 g of water, 30 g (0.187 mol) of diethylmalonate was suspended, the pH was adjusted to 10 with a few drops of a 5percent aqueous solution of sodium hydroxide and the liquid temperature was set to 10° C. (2) In another reactor, 45percent aqueous solution of sodium chlorate (402 g), 35percent hydrochloric acid (100 mL), and 35percent hydrogen peroxide (84 mL) were added while keep-ing at 35° C., and bubbling was performed by introducing air into the reactor so as to generate chlorine dioxide gas having a concentration of 8 vol percent and a purity of 99percent. (3) The introduction of chlorine dioxide gas generated in (2) above into the reactor of (1) above containing suspended diethyl malonate was started via an inlet tube, and the chlorine dioxide gas was blown into the reactor over 5 hours at from 13° C. to 18° C. while maintaining the pH at from 5 to 8 by the appropriate dropwise addition of the 5percent aqueous solution of sodium hydroxide. The amount ofthe 5percent aqueous solution of sodium hydroxide used was 180 g. (4) An aqueous solution of sodium thiosulfate was added to the homogeneous solution afier the completion of the reaction to reduce residual chlorine dioxide, and the extraction was performed with ethyl acetate. Ethyl acetate was distilled off from the extract by means of a rotary evaporator, and toluene was added to the residual oil obtained and dehydration was performed under reflux. Toluene was distilled off so as to obtain 28.9 g of diethyl ketomalonate (di- ethyl mesoxalate) as the desired product. The purity determined by gas chromatography was 99.7percent and the yield was89percent. Diethyl ketomalonate (diethyl mesoxalate); ‘H NMR (300 MHz, CDC13) ö ppm: 4.39 (q, J6.0 Hz, 2H), 1.36 (t, J=6.0 Hz, 3H). ‘3C NMR (300 MHz, CDC13) ö ppm: 178.2, 160.2,63.5, 13.9. GC-MS (El) mlz: 174 [M].
89% With chlorine dioxide; sodium hydroxide In water at 10 - 18℃; for 5 h; make the 30g (0.187mol) malonic acid diethyla ester aerosol in 100g water, to several drops of 5percent sodium hydroxide aqueous solution to regulate pH to 10, and become liquid 10 °C. (2) in another reaction tank, in maintaining the temperature 35 °C at the same time, added 45percent aqueous solution of sodium chlorate (402g), 35percent hydrochloric acid (100 ml) and 35percent hydrogen peroxide (84 ml), into the air for bubbling, thereby generating concentration 8vol percent, purity 99percent of the chlorine dioxide gas. (3) through an introducing pipe, will begin the above-mentioned (2) in the introduction of the chlorine dioxide gas to the suspended with the above-mentioned malonic acid diethyl ester (1) in the container, and, through the appropriate drop in 5percent aqueous sodium hydroxide solution in order to maintain the pH 5-8 at the same time of, in the 13 °C -18 ° C temperature, lasted 5 hours blows into the chlorine dioxide gas. The use of 5percent aqueous sodium hydroxide solution to 180 g. (4) the aqueous solution of sodium thiosulfate is added to the reaction in the completion of the homogeneous solution, reducing residual chlorine dioxide, and using ethyl acetate extraction. From the obtained liquid extract rotary evaporator removed by distillation in ethyl acetate, toluene is added to the obtained residue in shape, carry out dehydration reflux. Distillation after removing toluene, the target keto third acid di ethyl ester (in oxalic acid diethyl ester, diethylmesoxalate) 28.9 g. Gas chromatographic the measured purity of 99.7percent, the yield is 89percent.
100 %Chromat. With sodium chlorite; sodium acetate; acetic acid In water at 20℃; for 7 h; Examples 3-7; To a 50 mL eggplant-shaped flask equipped with a magnetic stirrer, diethyl malonate (DEM), sodium chlorite (Na chlorite), acetic acid, sodium acetate (Na acetate), and water were put in the reaction scale and the molar ratio as shown in following Table 1. Herein, results of pH measurement in the reaction system are shown in Table 1. Furthermore, the mixture was stirred under room temperature for the time shown in Table 1, and then analyzed by gas chromatography (GC) to calculate the yield rate. The results are shown in Table 1.
Reference: [1] Patent: US2016/194268, 2016, A1, . Location in patent: Paragraph 0212; 0213; 0214; 0215; 0216; 0217; 0218-0220
[2] Patent: CN105377803, 2016, A, . Location in patent: Paragraph 0232; 0233; 0237; 0238; 0239; 0240; 0241-0245
[3] American Chemical Journal, 1905, vol. 33, p. 603
[4] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1905, vol. 140, p. 1400[5] Annales de Chimie (Cachan, France), 1907, vol. <8> 12, p. 408
[6] Journal of the American Chemical Society, 1928, vol. 50, p. 3345
[7] American Chemical Journal, 1906, vol. 35, p. 483
[8] Organic Syntheses, 1930, vol. 10, p. 54
[9] American Chemical Journal, 1906, vol. 35, p. 483
[10] Journal of the Indian Chemical Society, 1986, vol. 63, p. 427 - 429
[11] Journal of Organic Chemistry, 1981, vol. 46, # 12, p. 2598 - 2599
[12] Tetrahedron Letters, 1984, vol. 25, # 34, p. 3743 - 3746
[13] Patent: US4584145, 1986, A,
[14] Patent: US2012/4443, 2012, A1, . Location in patent: Page/Page column 8
  • 7
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Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1910, vol. 29, p. 27[2] Chem. Zentralbl., 1909, vol. 80, # I, p. 1982
[3] Organic Syntheses 4 <New York 1925>, S. 27,
[4] Bulletin de la Societe Chimique de France, 1911, vol. <4> 9, p. 423
[5] Tetrahedron Letters, 2014, vol. 55, # 11, p. 1890 - 1893
  • 8
  • [ 685-87-0 ]
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Reference: [1] Russian Journal of Organic Chemistry, 1994, vol. 30, # 7.1, p. 1042 - 1044[2] Zhurnal Organicheskoi Khimii, 1994, vol. 30, # 7, p. 986 - 988
[3] Gazzetta Chimica Italiana, 1986, vol. 116, # 3, p. 163 - 164
[4] , 1965, vol. 1, # 6, p. 1130 - 1132[5] Zhurnal Organicheskoi Khimii, 1965, vol. 1, # 6, p. 1121 - 1124
[6] Chemische Berichte, 1891, vol. 24, p. 3002
  • 9
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Reference: [1] Synthetic Communications, 1994, vol. 24, # 5, p. 695 - 699
[2] Justus Liebigs Annalen der Chemie, 1969, vol. 723, p. 47 - 60
  • 10
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Reference: [1] Tetrahedron Letters, 1983, vol. 24, # 22, p. 2223 - 2226
  • 11
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Reference: [1] Tetrahedron Letters, 1984, vol. 25, # 34, p. 3743 - 3746
  • 12
  • [ 631-23-2 ]
  • [ 609-09-6 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1910, vol. 29, p. 121
[2] Journal of the American Chemical Society, 1911, vol. 33, p. 400
  • 13
  • [ 631-22-1 ]
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Reference: [1] Bulletin de la Societe Chimique de France, 1965, p. 3544 - 3549
[2] Journal of Organic Chemistry, 1981, vol. 46, # 12, p. 2598 - 2599
  • 14
  • [ 91473-89-1 ]
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Reference: [1] Liebigs Annalen der Chemie, 1985, # 2, p. 239 - 250
  • 15
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Reference: [1] Chemische Berichte, 1891, vol. 24, p. 3002
[2] Chemische Berichte, 1892, vol. 25, p. 3614
  • 16
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Reference: [1] Chemische Berichte, 1982, vol. 115, # 5, p. 2000 - 2002
  • 17
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Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 5, p. 891 - 892
  • 18
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Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 12, p. 2598 - 2599
  • 19
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Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1907, vol. 26, p. 381
  • 20
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Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1910, vol. 29, p. 121
  • 21
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  • [ 105-56-6 ]
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Reference: [1] Tetrahedron Letters, 1983, vol. 24, # 22, p. 2223 - 2226
  • 22
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Reference: [1] Chemische Berichte, 1982, vol. 115, # 5, p. 2000 - 2002
[2] Chemische Berichte, 1982, vol. 115, # 5, p. 2000 - 2002
  • 23
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Reference: [1] Chemische Berichte, 1894, vol. 27, p. 1305
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Reference: [1] Chemische Berichte, 1904, vol. 37, p. 1783
  • 25
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Reference: [1] Journal of the Chemical Society, 1933, p. 393
  • 26
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Reference: [1] Chemische Berichte, 1891, vol. 24, p. 3002
  • 27
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Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1907, vol. 26, p. 381
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Reference: [1] Chemische Berichte, 1891, vol. 24, p. 3002
  • 29
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Reference: [1] Journal of the Chemical Society, 1948, p. 1969
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Reference: [1] Tetrahedron Letters, 1984, vol. 25, # 39, p. 4375 - 4378
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Reference: [1] Tetrahedron Letters, 1984, vol. 25, # 39, p. 4375 - 4378
[2] Tetrahedron Letters, 1984, vol. 25, # 39, p. 4375 - 4378
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Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 3, p. 1833 - 1841
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