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[ CAS No. 641-74-7 ] {[proInfo.proName]}

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Chemical Structure| 641-74-7
Chemical Structure| 641-74-7
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Product Details of [ 641-74-7 ]

CAS No. :641-74-7 MDL No. :MFCD10698761
Formula : C6H10O4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 146.14 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 641-74-7 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 31.22
TPSA : 58.92 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) : -8.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.98
Log Po/w (XLOGP3) : -1.35
Log Po/w (WLOGP) : -1.49
Log Po/w (MLOGP) : -1.52
Log Po/w (SILICOS-IT) : -0.4
Consensus Log Po/w : -0.76

Druglikeness

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

Water Solubility

Log S (ESOL) : 0.1
Solubility : 186.0 mg/ml ; 1.27 mol/l
Class : Highly soluble
Log S (Ali) : 0.61
Solubility : 599.0 mg/ml ; 4.1 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 1.07
Solubility : 1730.0 mg/ml ; 11.8 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.38

Safety of [ 641-74-7 ]

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 [ 641-74-7 ]

* 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 [ 641-74-7 ]
  • Downstream synthetic route of [ 641-74-7 ]

[ 641-74-7 ] Synthesis Path-Upstream   1~22

  • 1
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  • [ 641-74-7 ]
YieldReaction ConditionsOperation in experiment
491 g at 170℃; for 20 h; Inert atmosphere 1350 g of crystalline mannitol was poured into a reduced pressure reactor equipped with a stirrer and melted by heating at 170 . Subsequently, 10 g of 98percent concentrated sulfuric acid was added to the obtained residue, and the reaction was carried out for 20 hours while introducing nitrogen gas at a flow rate of 200 ml / min under the conditions of 2 and 170 . The obtained product was cooled to 90 DEG C and 30 g of a 48 mass percent aqueous sodium hydroxide solution was added to obtain a crude isomannide. Subsequently, to the obtained crude isomannide,39 g of horseshoe-based woody activated carbon (trade name: Tyco K, manufactured by Futamura Chemical Co., Ltd.) was added and stirred for 3 hours to obtain a distillation object. Water was distilled off from the distillation object under the conditions of 5 ° C and 120 ° C and distillation was conducted while introducing nitrogen gas at a flow rate of 200 ml / min at 170 ° C under a reduced pressure of 0.3 kPa by a batch type distillation apparatus, 491 g was obtained. Further, the obtained distillation object was sampled, and in the same manner as in Example 1,The pH of the mixture was 10, and the pH was 10.
Reference: [1] Green Chemistry, 2015, vol. 17, # 2, p. A1176 - A1185
[2] Journal of Chemical Crystallography, 1997, vol. 27, # 3, p. 161 - 166
[3] Carbohydrate Research, 1980, vol. 79, p. 133 - 141
[4] Journal of Organometallic Chemistry, 1983, vol. 253, # 2, p. 249 - 252
[5] Journal of the American Chemical Society, 1946, vol. 68, p. 930,934
[6] Journal of the Chemical Society, 1947, p. 433,435[7] Journal of the Chemical Society, 1948, p. 2204,2206
[8] Journal of the Chemical Society, 1947, p. 433,435[9] Journal of the Chemical Society, 1948, p. 2204,2206
[10] Journal of the Chemical Society, 1947, p. 433,435[11] Journal of the Chemical Society, 1948, p. 2204,2206
[12] Journal of the Chemical Society, 1945, p. 4,6
[13] Journal of the Chemical Society, 1947, p. 433,435[14] Journal of the Chemical Society, 1948, p. 2204,2206
[15] Journal of the Chemical Society, 1950, p. 591,594
[16] Carbohydrate Research, 1990, vol. 205, # 1, p. 191 - 202
[17] Patent: US2004/110969, 2004, A1, . Location in patent: Page 6
[18] Patent: KR2016/28403, 2016, A, . Location in patent: Paragraph 0077; 0078
[19] Green Chemistry, 2018, vol. 20, # 3, p. 634 - 640
  • 2
  • [ 1707-77-3 ]
  • [ 641-74-7 ]
Reference: [1] Patent: WO2017/189477, 2017, A1, . Location in patent: Paragraph 0036; 0037
  • 3
  • [ 652-67-5 ]
  • [ 641-74-7 ]
  • [ 641-74-7 ]
YieldReaction ConditionsOperation in experiment
60 %Spectr. With 5% active carbon-supported ruthenium; hydrogen In water at 220℃; for 3 h; EXAMPLE 1; In a typical experiment the isosorbide solution in water was prepared by adjusting the pH using sodium hydroxide, and degassed with nitrogen by bubbling gas into the solution for 1 hour. The heterogeneous catalyst was weighed in air, placed in a glass liner with the stirring bar, and the liner was introduced into the reactor and the atmosphere was purged twice with nitrogen. The substrate solution was then added via syringe and the reactor was closed and purged 3 times with nitrogen. After purging of the gas lines, hydrogen was used to purge the reactor (3 times). The desired hydrogen pressure was then applied, stirring was started and heating began (typically heating was achieved in 25 minutes). The reaction time started when the desired temperature was reached. [0042] After reaction, the reactor was allowed to cool down to room temperature and the excess gas pressure was released. The crude solution was filtered twice using two microfilters (Millipore, 0.45 μm then 0.20 μm), pH was measured, and the crude reaction mixture was dried in an oven overnight (T=60° C.). The crude syrup was then dried further in a dessicator under high vacuum for ca. 5 hours before analysis. [0043] Experiments 1-12 are outlined in Table 1 below. The first set of reactions (code 1 to 6) was performed using 1.1 g of isosorbide in 30 mL of water with 10 to 20 wt percent of a 5percent Ru/C catalyst at 50° C. for 4 to 24 hours. The crude mixtures were analyzed by 1H NMR is D2O after drying of an aliquot of the solution. No epimerization was observed and only isosorbide was recovered. [0045] Reactions 7 to 10 were used to study the influence of temperature on the reaction and due to the closed system of the reactors, the initial pressure of hydrogen increased from 1 bar at room temperature to 24.5 bar at 220° C. for reaction 10. NMR analysis showed no conversion. [0046] For reaction 11 and 12, the initial hydrogen pressure at room temperature was set at 30.0 bar and 54.5 bar, respectively. The internal pressure increased to 47.0 bar for reaction 11 and to 81.1 bar for reaction 12 at 220° C. Aliquots of the crude reactions mixtures were analyzed with NMR, which showed that for both reactions the epimerization of isosorbide had occurred, and the ratios observed between the three isomers indicates that the thermodynamic equilibrium had been reached within the reaction time of 3 h. EXAMPLE 2; As compared to Example 1, a number of reaction conditions were varied. First the substrate concentration was increased to 33 wt/wt percent, and the catalyst loading was decreased from 20 wt percent to 4 wt percent (Table 2). The reactions were performed at 220° C. for 2 hours using different hydrogen pressures. EXAMPLE 3; A further set of experiments was performed to evaluate a) the effect of increasing the substrate concentration to 50 wt/wt percent isosorbide in water to obtain a good comparison with U.S. Pat. No. 3,023,223, and b) the influence of the support material. All reactions were performed at catalyst loading of 4 wt percent, at 220° C. with a reaction time of 4 hours. The hydrogen pressure was set at 40 bar at room temperature and reached approx. 58 bar at the reaction temperature. EXAMPLE 4; A next set of experiments was performed by tuning the initial pH (Table 4, 5, and 6). For all reactions the substrate concentration was fixed at 50 wt/wt percent isosorbide (10 g) in water, the catalyst used was the 5percent Ru/C (Escat 4401), the temperature was set at 220° C. and hydrogen pressure was tuned at approx. 40 bar at room temperature leading to a total pressure of approx. 60 bar at 220° C. [0050] It is important to notice that the reaction time relates to the time that the reaction mixture is maintained at the experiment temperature, therefore this time is not taking into account the heating time (approx. 30 min in all cases), and the cooling time back to room temperature (approx. 2 hours) The reactions were magnetically stirred and the stirring (1000 rpm) started after the pressurization of the reactors and before the heating started to avoid overshooting of the temperature. EXAMPLE 5; The effect of the catalyst loading on the reaction rate was studied next (Table 7). By decreasing the catalyst loading from 4 wt percent to 2 wt percent the thermodynamic equilibrium was not reached after 1 hour reaction (reaction 49) but was achieved after 2 hours, however with a mass loss of 6.7percent (reaction 56). Using 1 wt percent of catalyst the results appeared similar with the thermodynamic equilibrium reached after 2 hours and a mass loss reduced to 1.3percent (reaction 50, 55). Lower catalyst loading showed no activity (reaction 41). EXAMPLE 6; Different metal catalysts on different supports were tested using the standard reaction conditions and the results were compared to Ru/C (Table 8). EXAMPLE 7; A series of reactions was performed at different temperatures (Table 10). EXAMPLE 8; A large scale reaction was performed in a 600 mL Parr reactor with 200 g of isosorbide (1.37 mol) in 200 mL of water at pH 8 (mechanical stirrer at 500 rpm). Ruthenium (5percent) on carbon (reduced, 50percent water paste, Escat 4401) was used at a loading of 1 wt percent. The reaction vessel was pressurized with 40 bar of hydrogen and heated at 220° C. for 2 hours. Aliquots of the reaction mixture were taken during the heating time and along the reaction. Those aliquots were obtained by manually opening the deep tube tab, then by flushing the tube (2-3 mL), and finally by collecting the sample (2 mL), which was analyzed following the standard procedure (Table 11).
Reference: [1] Patent: EP2615093, 2013, A1, . Location in patent: Paragraph 0109
[2] Patent: WO2013/107735, 2013, A1, . Location in patent: Paragraph 00111
[3] Patent: US2014/371472, 2014, A1, . Location in patent: Paragraph 0041 - 0055
[4] ChemSusChem, 2013, vol. 6, # 4, p. 693 - 700
[5] Patent: WO2016/137833, 2016, A1, . Location in patent: Paragraph 00110-00113
[6] Advanced Synthesis and Catalysis, 2018, vol. 360, # 12, p. 2358 - 2363
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Reference: [1] ACS Catalysis, 2017, vol. 7, # 7, p. 4828 - 4834
  • 5
  • [ 50-70-4 ]
  • [ 616-38-6 ]
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  • [ 5306-85-4 ]
Reference: [1] ChemSusChem, 2017, vol. 10, # 1, p. 53 - 57
  • 6
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Reference: [1] ACS Catalysis, 2017, vol. 7, # 7, p. 4828 - 4834
[2] Carbohydrate Research, 1990, vol. 205, # 1, p. 191 - 202
[3] Carbohydrate Research, 1990, vol. 205, # 1, p. 191 - 202
[4] Carbohydrate Research, 1990, vol. 205, # 1, p. 191 - 202
[5] Carbohydrate Research, 1990, vol. 205, # 1, p. 191 - 202
  • 7
  • [ 69-65-8 ]
  • [ 141-78-6 ]
  • [ 73952-88-2 ]
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Reference: [1] Carbohydrate Research, 1980, vol. 79, p. 133 - 141
  • 8
  • [ 82064-06-0 ]
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Reference: [1] Chemische Berichte, 1934, vol. 67, p. 1582,1586
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 930,934
  • 9
  • [ 69-65-8 ]
  • [ 116-11-0 ]
  • [ 65729-81-9 ]
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Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 24, p. 9406 - 9411
  • 10
  • [ 57-50-1 ]
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Reference: [1] Journal of the Chemical Society, 1947, p. 433,435[2] Journal of the Chemical Society, 1948, p. 2204,2206
[3] Journal of the Chemical Society, 1947, p. 433,435[4] Journal of the Chemical Society, 1948, p. 2204,2206
  • 11
  • [ 7251-85-6 ]
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Reference: [1] Journal of the Chemical Society, 1945, p. 4,6
  • 12
  • [ 7726-97-8 ]
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Reference: [1] Journal of the Chemical Society, 1945, p. 4,6
  • 13
  • [ 69-65-8 ]
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  • [ 7726-97-8 ]
  • [ 492-93-3 ]
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Reference: [1] RSC Advances, 2014, vol. 4, # 85, p. 45575 - 45578
[2] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1981, vol. 35, # 6, p. 441 - 450
  • 14
  • [ 69-65-8 ]
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  • [ 492-93-3 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 433,435[2] Journal of the Chemical Society, 1948, p. 2204,2206
  • 15
  • [ 56-23-5 ]
  • [ 69-65-8 ]
  • [ 104-15-4 ]
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Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 930,934
[2] Journal of the Chemical Society, 1947, p. 433,435[3] Journal of the Chemical Society, 1948, p. 2204,2206
  • 16
  • [ 56-23-5 ]
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  • [ 7664-93-9 ]
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Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 930,934
[2] Journal of the Chemical Society, 1947, p. 433,435[3] Journal of the Chemical Society, 1948, p. 2204,2206
  • 17
  • [ 69-65-8 ]
  • [ 641-74-7 ]
  • [ 7726-97-8 ]
  • [ 492-93-3 ]
  • [ 41107-82-8 ]
Reference: [1] Synthesis, 1994, # 10, p. 1087 - 1090
  • 18
  • [ 69-65-8 ]
  • [ 124379-13-1 ]
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  • [ 7726-97-8 ]
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Reference: [1] Carbohydrate research, 2002, vol. 337, # 14, p. 1261 - 1268
  • 19
  • [ 67-56-1 ]
  • [ 124-41-4 ]
  • [ 54522-28-0 ]
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Reference: [1] Journal of the American Chemical Society, 1956, vol. 78, p. 5916,5919
  • 20
  • [ 7647-01-0 ]
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Reference: [1] Journal of the Chemical Society, 1945, p. 4,6
  • 21
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  • [ 69-65-8 ]
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Reference: [1] Journal of the Chemical Society, 1947, p. 433,435[2] Journal of the Chemical Society, 1948, p. 2204,2206
[3] Journal of the Chemical Society, 1944, p. 157
[4] Journal of the Chemical Society, 1945, p. 7
  • 22
  • [ 50-70-4 ]
  • [ 616-38-6 ]
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  • [ 5306-85-4 ]
Reference: [1] ChemSusChem, 2017, vol. 10, # 1, p. 53 - 57
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