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[ CAS No. 594-61-6 ] {[proInfo.proName]}

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Chemical Structure| 594-61-6
Chemical Structure| 594-61-6
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Product Details of [ 594-61-6 ]

CAS No. :594-61-6 MDL No. :MFCD00004459
Formula : C4H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :BWLBGMIXKSTLSX-UHFFFAOYSA-N
M.W : 104.10 Pubchem ID :11671
Synonyms :

Calculated chemistry of [ 594-61-6 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.75
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 24.31
TPSA : 57.53 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) : -7.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.79
Log Po/w (XLOGP3) : -0.36
Log Po/w (WLOGP) : -0.16
Log Po/w (MLOGP) : -0.39
Log Po/w (SILICOS-IT) : -0.65
Consensus Log Po/w : -0.15

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -0.19
Solubility : 66.8 mg/ml ; 0.642 mol/l
Class : Very soluble
Log S (Ali) : -0.39
Solubility : 42.8 mg/ml ; 0.411 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.57
Solubility : 387.0 mg/ml ; 3.72 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 594-61-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 594-61-6 ]

* 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 [ 594-61-6 ]
  • Downstream synthetic route of [ 594-61-6 ]

[ 594-61-6 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 855636-80-5 ]
  • [ 594-61-6 ]
  • [ 13027-88-8 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 582,583,584
  • 2
  • [ 594-61-6 ]
  • [ 13027-88-8 ]
Reference: [1] J. Appl. Chem. USSR (Engl. Transl.), 1982, vol. 55, # 7, p. 1487 - 1490[2] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1982, vol. 55, # 7, p. 1617 - 1621
  • 3
  • [ 7647-01-0 ]
  • [ 75-86-5 ]
  • [ 594-61-6 ]
  • [ 49562-37-0 ]
  • [ 13027-88-8 ]
Reference: [1] Patent: US2431468, 1945, ,
[2] Patent: US2229897, 1940, ,
[3] Bulletin des Societes Chimiques Belges, 1930, vol. 39, p. 563[4] Bulletin des Societes Chimiques Belges, 1931, vol. 40, p. 475
  • 4
  • [ 7664-93-9 ]
  • [ 75-86-5 ]
  • [ 594-61-6 ]
  • [ 49562-37-0 ]
  • [ 13027-88-8 ]
Reference: [1] Patent: US2431468, 1945, ,
[2] Patent: US2229897, 1940, ,
[3] Bulletin des Societes Chimiques Belges, 1930, vol. 39, p. 563[4] Bulletin des Societes Chimiques Belges, 1931, vol. 40, p. 475
  • 5
  • [ 56-23-5 ]
  • [ 855636-80-5 ]
  • [ 594-61-6 ]
  • [ 13027-88-8 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 582,583,584
  • 6
  • [ 594-61-6 ]
  • [ 75-36-5 ]
  • [ 40635-66-3 ]
Reference: [1] Chemische Berichte, 1975, vol. 108, p. 3210 - 3223
[2] Journal of the American Chemical Society, 1973, vol. 95, # 12, p. 4016 - 4025
[3] Journal of Heterocyclic Chemistry, 1978, vol. 15, p. 63 - 64
  • 7
  • [ 594-61-6 ]
  • [ 108-24-7 ]
  • [ 40635-66-3 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1973, vol. 9, p. 2258 - 2261[2] Zhurnal Organicheskoi Khimii, 1973, vol. 9, p. 2241 - 2245
  • 8
  • [ 594-61-6 ]
  • [ 108-95-2 ]
  • [ 943-45-3 ]
Reference: [1] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1906, vol. <5> 15 I, p. 582[2] Gazzetta Chimica Italiana, 1906, vol. 36 II, p. 334
  • 9
  • [ 56-23-5 ]
  • [ 594-61-6 ]
  • [ 67-64-1 ]
  • [ 108-95-2 ]
  • [ 943-45-3 ]
Reference: [1] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1906, vol. <5> 15 I, p. 582[2] Gazzetta Chimica Italiana, 1906, vol. 36 II, p. 334
[3] Gazzetta Chimica Italiana, 1906, vol. 36 II, p. 334
  • 10
  • [ 594-61-6 ]
  • [ 100-39-0 ]
  • [ 19444-23-6 ]
YieldReaction ConditionsOperation in experiment
91% With N-ethyl-N,N-diisopropylamine In acetonitrile In steps 1-4, 2-hydroxy-isobutyric acid was protected with benzyl bromide, alkylated with ethyl iodide, deprotected, and esterified to afford 2-ethoxy-isobutyric acid chloromethyl ester.
83%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 5 - 20℃; for 1 h;
Stage #2: at 100℃; for 3 h; Microwave irradiation
To a solution of 2-hydroxy-2-methylpropanoic acid (500 mg, 4.80 mmol) in dry THF (10 ml), NaH (60percent dispersion in mineral oil, 192 mg, 4.80 mmol) was added portionwise at 5° C. The resulting mixture was stirred 1 hour at RT. The solvent was removed, the residue was suspended in dry DMF (7 ml), and (bromomethyl)benzene (821 mg, 4.80 mmol) was added followed by a catalytic amount of KI. The reaction was heated under microwave irradiation at 100° C. for 3 hours. After cooling, the solvent was evaporated and the residue was partitioned between water and EtOAc; the organic phase was washed with brine, dried over sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography on silica gel (EtOAc/petroleum ether=1/1) affording benzyl 2-hydroxy-2-methylpropanoate as a yellow liquid (773 mg, 3.98 mmol, 83percent yield).
70% With tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate In dichloromethane; water at 20℃; for 60 h; A solution of 2-hydroxy-2-methylpropanoic acid (101, 9.27 g, 89.1 mmol), sodium bicarbonate (7.49 g, 89.1 mmol), benzyl bromide (16.8 g, 98.0 mmol) and tetrabutylammonium iodide (32.9 g, 89.1 mmol) in H2O/CH2C12 (1 : 1 , 300 mL) was stirred at room temperature for 2.5 d. The reaction mixture was diluted with CH2Cl2 (200 mL) and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (2 x 50 mL) and the combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 7:3 hexanes/EtOAc) provided 102 (12.2 g, 70percent) as a yellow oil: 1H NMR (300 MHz, CDCl3) δ 7.37-7.32 (m, 5H), 5.20 (s, 2H), 3.05 (s, I H), 1.45 (s, 6H).
Reference: [1] Tetrahedron, 2001, vol. 57, # 20, p. 4323 - 4336
[2] Patent: US2008/9474, 2008, A1, . Location in patent: Page/Page column 19
[3] Patent: US2013/79313, 2013, A1, . Location in patent: Paragraph 1009
[4] Patent: WO2009/73138, 2009, A2, . Location in patent: Page/Page column 81
[5] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 11, p. 1541 - 1546
  • 11
  • [ 594-61-6 ]
  • [ 7051-34-5 ]
  • [ 19444-23-6 ]
YieldReaction ConditionsOperation in experiment
83%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 5 - 20℃; for 1 h;
Stage #2: With potassium iodide In N,N-dimethyl-formamide at 100℃; for 3 h; Microwave irradiation
To a solution of 2-hydroxy-2-methylpropanoic acid (500 mg, 4.80 mmol) in dry THF (10 ml), NaH (60percent dispersion in mineral oil, 192 mg, 4.80 mmol) was added portionwise at 5°C. The resulting mixture was stirred lh at RT. The solvent was removed, the residue was suspended in dry DMF (7 ml) and (bromomethyl)benzene (821 mg, 4.80 mmol) was added followed by a catalytic amount of KI. The reaction was heated under microwave irradiation at 100°C for 3h. After cooling the solvent was evaporated and the residue was partitioned between water and EtOAc; the organic phase was washed with brine, dried over sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography on silica gel (EtO Ac/petroleum ether = 1/1) affording benzyl 2-hydroxy-2- methylpropanoate as a yellow liquid (773 mg, 3.98 mmol, 83percent yield).
Reference: [1] Patent: WO2013/45280, 2013, A1, . Location in patent: Page/Page column 266
  • 12
  • [ 594-61-6 ]
  • [ 7285-83-8 ]
  • [ 19444-23-6 ]
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 36, p. 7997 - 8002
  • 13
  • [ 594-61-6 ]
  • [ 100-51-6 ]
  • [ 19444-23-6 ]
Reference: [1] Patent: US2336317, 1940, ,
  • 14
  • [ 594-61-6 ]
  • [ 98-88-4 ]
  • [ 58570-00-6 ]
YieldReaction ConditionsOperation in experiment
82% With pyridine In acetonitrile at 20℃; for 0.666667 h; Example 1
2-(Benzoyloxy)-2-methylpropanoic acid
2-Hydroxyisobutyric acid (50 g) was dissolved in acetonitrile (480 mL).
To this solution, pyridine (78 mL) was added, and then, benzoyl chloride (56 mL) was added thereto.
The resulting solution was stirred at room temperature for 40 minutes.
To the reaction mixture, 2 N hydrochloric acid (300 mL) was added to acidify the solution, and then, extraction was performed with ethyl acetate (400 mL*2).
The organic layers were combined and dried over magnesium sulfate.
After magnesium sulfate was removed by filtration, the solvent was concentrated under reduced pressure.
The resulting residue was recrystallized from tert-butylmethyl ether/n-heptane, whereby the title compound (82 g, 82percent) having the following physical properties was obtained.
TLC (Rf value): 0.37 (ethyl acetate)
NMR (300 MHz, CDCl3): δ 8.20-9.40 (br, 1H), 8.01-8.06 (m, 2H), 7.53-7.59 (m, 1H), 7.40-7.46 (m, 2H), 1.73 (s, 6H)
Reference: [1] Patent: US2013/245074, 2013, A1, . Location in patent: Paragraph 0349-0352
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