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[ CAS No. 87-91-2 ] {[proInfo.proName]}

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Chemical Structure| 87-91-2
Chemical Structure| 87-91-2
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Product Details of [ 87-91-2 ]

CAS No. :87-91-2 MDL No. :MFCD00009143
Formula : C8H14O6 Boiling Point : -
Linear Structure Formula :- InChI Key :YSAVZVORKRDODB-PHDIDXHHSA-N
M.W : 206.19 Pubchem ID :6993580
Synonyms :

Calculated chemistry of [ 87-91-2 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.75
Num. rotatable bonds : 7
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 45.46
TPSA : 93.06 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) : -7.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.88
Log Po/w (XLOGP3) : -0.29
Log Po/w (WLOGP) : -1.17
Log Po/w (MLOGP) : -0.71
Log Po/w (SILICOS-IT) : -0.22
Consensus Log Po/w : -0.1

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.47
Solubility : 69.3 mg/ml ; 0.336 mol/l
Class : Very soluble
Log S (Ali) : -1.2
Solubility : 12.9 mg/ml ; 0.0624 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.2
Solubility : 330.0 mg/ml ; 1.6 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.14

Safety of [ 87-91-2 ]

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 [ 87-91-2 ]

* 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 [ 87-91-2 ]
  • Downstream synthetic route of [ 87-91-2 ]

[ 87-91-2 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 50-00-0 ]
  • [ 87-91-2 ]
  • [ 1080-79-1 ]
YieldReaction ConditionsOperation in experiment
60%
Stage #1: With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In ethyl acetate at 20℃; for 3 h;
Stage #2: With ammonium acetate In water; acetic acid; ethyl acetate at 10 - 50℃; for 3.5 h; Cooling with ice
(Reference Example 3) Diethyl 1H-imidazole-4,5-dicarboxylate
Reference Example 3
was carried out under non-light-shielding conditions.
To a solution of L-tartaric acid diethyl ester (2.0 g) in ethyl acetate (34.2 ml), 1,3-dibromo-5,5-dimethylhydantoin (3.3 g) was added, and the reaction solution was stirred at room temperature for 3 hours.
To the reaction solution, acetic acid (17 ml) was added, and subsequently 36percent aqueous formaldehyde solution (3.45 ml) was added under ice cooling at an internal temperature of 10°C or below, followed by addition of ammonium acetate (17.2 g) at an internal temperature of 10°C or below.
The reaction solution was stirred at room temperature for 30 minutes, followed by stirring at 50°C for 3 hours.
To the reaction solution, 5N sodium hydroxide was added, and the aqueous layer was extracted with ethyl acetate.
The organic layers were combined, and dried over magnesium sulfate.
Quantitative analysis of the resulting ethyl acetate solution by HPLC showed that the title compound (1.24 g, yield: 60percent) was obtained.
Condition for HPLC analysis is identical with that for Example 5.
From the results of Reference Example 3 and Example 5, it was shown that the production method of the present invention [the method for producing compound (5) from compound (1)] was superior to the reaction indicated in the known Method X in terms of yield even under non-light-shielding conditions.
Reference: [1] Patent: EP2298763, 2011, A1, . Location in patent: Page/Page column 31
  • 2
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  • [ 1080-79-1 ]
Reference: [1] Patent: EP2298763, 2011, A1,
  • 3
  • [ 87-91-2 ]
  • [ 24720-64-7 ]
  • [ 62054-49-3 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 5, p. 1816 - 1822
  • 4
  • [ 87-91-2 ]
  • [ 7554-28-1 ]
Reference: [1] Tetrahedron Letters, 1989, vol. 30, # 22, p. 2945 - 2948
[2] Angewandte Chemie - International Edition, 2008, vol. 47, # 23, p. 4335 - 4338
[3] Chemische Berichte, 1994, vol. 127, # 8, p. 1447 - 1458
[4] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 2157 - 2165
[5] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 2157 - 2165
  • 5
  • [ 57968-71-5 ]
  • [ 13811-71-7 ]
  • [ 87-91-2 ]
YieldReaction ConditionsOperation in experiment
11.5 % ee With (S)-aminopropyl alcohol(at)silica 1 In hexane; isopropyl alcohol at 20℃; for 1 h; Resolution of racemate; Inert atmosphere Example-32; To a medium pressure chromatographic column, slurry of (S)-aminopropyl alcohol(at)silica 1 (0.512 mol percent) in hexane and isopropanol (8:2) was packed in a 260.x.16 mm glass column using medium-pressure (0.5 kp/cm2) of nitrogen at room temperature. The solution of racemic diethyl-tartrate (0.50 mol percent) in isopropanol/hexane (1:1) was loaded on packed column that was equilibrated for 1 h. The elution of fractions was done at the pressure mentioned above. Each fraction was subjected to HPLC analysis using an appropriate Chiralpak AD column, eluent hexane/isopropanol (8:2) at 220nm. The enantiomeric excess of diethyl-tartrate found 11.5percent.
Reference: [1] Patent: US2010/286425, 2010, A1, . Location in patent: Page/Page column 11-12
  • 6
  • [ 64-17-5 ]
  • [ 87-69-4 ]
  • [ 87-91-2 ]
YieldReaction ConditionsOperation in experiment
96.2% at 0 - 50℃; for 3.5 h; (1)Into 500mL three-necked glass flask L - (+) - tartaric acid 30g,Then take the amount of anhydrous ethanol 150mL added to three-necked flask,Turn on stirringControl the internal temperature at 0 ~ 30 ,95.4 g of thionyl chloride was added dropwise,Time is 1.5h,Dropping the process of exothermic,After the addition was completed, the temperature was raised to 50 ° C,Reaction 2h,Then vacuum distillation,Remove ethanol,Get L - (+) - diethyl tartrate crude;(2)To the L - (+) - diethyl tartrate crude was added potassium bicarbonate 3.3g,Warmed to 20 ° C,Stirring reaction 3h,Filter to remove the solid,39.6 g of L - (+) - tartaric acid diethyl ester was obtained as a colorless or light yellow oily liquid,The molar yield was 96.2percentAfter testing,Product purity is 99.4percent.
94% at 25℃; for 12 h; Cooling with ice (1) under the ice water bath, to tartaric acid L - (substituted (I - 1 - 1), 100 g, 0.67 µM) anhydrous ethanol (600 ml) is dropped in the adds the chlorination sulfoxide (107 ml), at room temperature (about 25 °C) reaction 12 h, at low temperature the solvent is removed under reduced pressure, dissolved in EtOAc, saturated sodium bicarbonate washing to neutral, dried, concentrated under reduced pressure to remove the solvent, and concentration to obtain a colorless oil of, substituted (I - 1 - 2) compound of formula (138 g, yield 94percent).
88% for 10 h; Reflux A mixture of (2R,3R)-(+)-tartaric acid 1 (22.0 g, 150 mmol) and a catalytic amount of H2SO4 in EtOH (100 mL) was stirred at reflux for 10 h. After completion of the reaction, the mixture was concentrated in vacuo. A silica gel mesh was prepared from the residue and submitted to flash chromatography (silica gel: EtOAc/hexane as eluent) to provide 2 (26.4 g, 88percent). 1H-NMR (CDCl3, δ=7.26 ppm, 400 MHz,): 1.27 (t, J = 7.2 Hz, 6H), 3.36 (d, J = 6.6 Hz, 2H), 4.26 (q, J = 7.2 Hz, 4H), 4.5 (d, J = 6Hz, 2H).
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 36, p. 4851 - 4853
[2] RSC Advances, 2015, vol. 5, # 15, p. 11687 - 11696
[3] Patent: CN107337603, 2017, A, . Location in patent: Paragraph 0025; 0026; 0027; 0028; 0029; 0030; 0031-0040
[4] Journal of Organic Chemistry, 2012, vol. 77, # 19, p. 8465 - 8479,15
[5] Patent: CN106966943, 2017, A, . Location in patent: Paragraph 0090; 0091
[6] Organic Letters, 2005, vol. 7, # 22, p. 5047 - 5050
[7] Tetrahedron, 2007, vol. 63, # 35, p. 8645 - 8657
[8] Tetrahedron Asymmetry, 2001, vol. 12, # 22, p. 3081 - 3088
[9] Journal of Enzyme Inhibition and Medicinal Chemistry, 2016, vol. 31, # 2, p. 219 - 228
[10] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 7, p. 805 - 812
[11] RSC Advances, 2013, vol. 3, # 6, p. 1976 - 1986
[12] Bulletin of the Korean Chemical Society, 2016, vol. 37, # 12, p. 1910 - 1911
[13] Ann.Chim.applic., 1935, vol. 25, p. 321[14] Chem. Zentralbl., 1935, vol. 106, # II, p. 3084
[15] Annales de Chimie (Cachan, France), 1943, vol. <11>18, p. 155[16] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1943, vol. 216, p. 64
[17] Monatshefte fuer Chemie, 1949, vol. 80, p. 256,259
[18] Chemische Berichte, 1936, vol. 69, p. 2279
[19] Ciencia, 1947, vol. 8, p. 175[20] Chem.Abstr., 1949, p. 127
[21] Collection of Czechoslovak Chemical Communications, 1977, vol. 42, p. 3069 - 3078
[22] Canadian Journal of Chemistry, 1963, vol. 41, p. 393 - 398
[23] Helvetica Chimica Acta, 1977, vol. 60, p. 301 - 325
[24] Tetrahedron Asymmetry, 2006, vol. 17, # 14, p. 2101 - 2107
[25] Tetrahedron, 1984, vol. 40, # 22, p. 4617 - 4623
[26] Tetrahedron, 2007, vol. 63, # 27, p. 6346 - 6357
[27] Chemistry Letters, 2007, vol. 36, # 12, p. 1436 - 1437
[28] Tetrahedron Asymmetry, 2011, vol. 22, # 3, p. 257 - 263
[29] RSC Advances, 2013, vol. 3, # 43, p. 20298 - 20307
  • 7
  • [ 64-17-5 ]
  • [ 87-69-4 ]
  • [ 87-91-2 ]
Reference: [1] Journal of the Chemical Society, 1898, vol. 73, p. 302
[2] Journal of the Chemical Society, 1922, vol. 121, p. 536,539
[3] Yakugaku Zasshi, 1927, p. 150[4] Chem. Zentralbl., 1928, vol. 99, # I, p. 1643
[5] Chemische Berichte, 1895, vol. 28, p. 3255
[6] Bulletin des Societes Chimiques Belges, 1920, vol. 29, p. 61,66[7] Chem. Zentralbl., 1920, vol. 91, # I, p. 817
[8] Chemische Berichte, 1895, vol. 28, p. 3255
[9] Journal of the American Chemical Society, 1921, vol. 43, p. 369
[10] Anales de la Real Sociedad Espanola de Fisica y Quimica, vol. 23, p. 415[11] Chem. Zentralbl., 1926, vol. 97, # I, p. 877
[12] Journal of the Chemical Society, 1922, vol. 121, p. 536,539
[13] Journal of the Chemical Society, 1910, vol. 79, p. 168
[14] Journal of the Chemical Society, 1929, p. 1897
  • 8
  • [ 57968-71-5 ]
  • [ 13811-71-7 ]
  • [ 87-91-2 ]
YieldReaction ConditionsOperation in experiment
11.5 % ee With (S)-aminopropyl alcohol(at)silica 1 In hexane; isopropyl alcohol at 20℃; for 1 h; Resolution of racemate; Inert atmosphere Example-32; To a medium pressure chromatographic column, slurry of (S)-aminopropyl alcohol(at)silica 1 (0.512 mol percent) in hexane and isopropanol (8:2) was packed in a 260.x.16 mm glass column using medium-pressure (0.5 kp/cm2) of nitrogen at room temperature. The solution of racemic diethyl-tartrate (0.50 mol percent) in isopropanol/hexane (1:1) was loaded on packed column that was equilibrated for 1 h. The elution of fractions was done at the pressure mentioned above. Each fraction was subjected to HPLC analysis using an appropriate Chiralpak AD column, eluent hexane/isopropanol (8:2) at 220nm. The enantiomeric excess of diethyl-tartrate found 11.5percent.
Reference: [1] Patent: US2010/286425, 2010, A1, . Location in patent: Page/Page column 11-12
  • 9
  • [ 64-17-5 ]
  • [ 87-69-4 ]
  • [ 81-23-2 ]
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  • [ 52718-49-7 ]
Reference: [1] Patent: US2005/113352, 2005, A1, . Location in patent: Page/Page column 1; 6
  • 10
  • [ 623-91-6 ]
  • [ 87-91-2 ]
Reference: [1] Journal of the American Chemical Society, 1945, vol. 67, p. 486
  • 11
  • [ 64-17-5 ]
  • [ 622-00-4 ]
  • [ 87-91-2 ]
Reference: [1] Tetrahedron, 1992, vol. 48, # 40, p. 8775 - 8780
  • 12
  • [ 111-87-5 ]
  • [ 87-91-2 ]
  • [ 18536-88-4 ]
  • [ 52322-14-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2008, vol. 6, # 15, p. 2790 - 2795
  • 13
  • [ 87-69-4 ]
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Reference: [1] Synlett, 2012, vol. 23, # 6, p. 855 - 858
  • 14
  • [ 75-03-6 ]
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Reference: [1] Journal of the Chemical Society, 1899, vol. 75, p. 154
[2] Journal of the Chemical Society, 1898, vol. 73, p. 302
  • 15
  • [ 64-17-5 ]
  • [ 608-89-9 ]
  • [ 87-91-2 ]
Reference: [1] Annales de Chimie (Cachan, France), 1863, vol. <3>68, p. 263
[2] Journal of the Chemical Society, 1898, vol. 73, p. 322,323
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