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[ CAS No. 10495-09-7 ] {[proInfo.proName]}

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Chemical Structure| 10495-09-7
Chemical Structure| 10495-09-7
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Product Details of [ 10495-09-7 ]

CAS No. :10495-09-7 MDL No. :MFCD22494947
Formula : C10H18O5 Boiling Point : -
Linear Structure Formula :- InChI Key :HYVRRAANXHHPGH-UHFFFAOYSA-N
M.W : 218.25 Pubchem ID :11138577
Synonyms :

Calculated chemistry of [ 10495-09-7 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 9
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 53.84
TPSA : 61.83 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) : -6.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.81
Log Po/w (XLOGP3) : 0.94
Log Po/w (WLOGP) : 0.91
Log Po/w (MLOGP) : 0.32
Log Po/w (SILICOS-IT) : 1.45
Consensus Log Po/w : 1.28

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.19
Solubility : 14.0 mg/ml ; 0.0644 mol/l
Class : Very soluble
Log S (Ali) : -1.83
Solubility : 3.26 mg/ml ; 0.015 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.84
Solubility : 3.18 mg/ml ; 0.0146 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.66

Safety of [ 10495-09-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 10495-09-7 ]

* 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 [ 10495-09-7 ]
  • Downstream synthetic route of [ 10495-09-7 ]

[ 10495-09-7 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 141-78-6 ]
  • [ 6065-82-3 ]
  • [ 10495-09-7 ]
YieldReaction ConditionsOperation in experiment
93%
Stage #1: at 20 - 60℃; for 20 h; Inert atmosphere
Stage #2: With hydrogenchloride In ethanol; water
Intermediate 82: ethyl 4,4-bis(ethyloxy)-3-oxobutanoate Under an atmosphere of nitrogen, sodium (6.3g, 274mmol) was added in 500mg portions over 1 hour to a solution of ethyl bis(ethyloxy)acetate (30.3ml_, 170mmol) in ethyl acetate (56ml_) at ambient temperature. There was a slow exotherm to afford a red/brown solution. The solution was heated at 6O0C for 2 hours and then stirred at ambient temperature for 18 hours. The mixture was cautiously treated with ethanol (5ml_) and water (5OmL) and then acidified to pH6 by the addition of 1 M aqueous hydrochloric acid (about 16OmL). The mixture was extracted with dichloromethane (3 x 10OmL) and the combined organics were washed with brine (2 x 10OmL) and evaporated to dryness to afford the title compound (34.6g, 159mmol, 93percent yield). 1H NMR (400 MHz, DMSO-d6) δ 1.06 - 1.20 (9H,m), 3.46 - 3.62 (6H,m), 4.08 (2H, q, J= 7.6 Hz), 4.77 (1 H, s).
81% With sodium hydride In tetrahydrofuran at 20℃; for 20.5 h; Heating / reflux Ethyl 4,4-diethoxy-3-oxobutanoate (Scheme 1, A). To a stirring suspension of sodium hydride (5.12 g, 213 mmol) in anhydrous tetrahydrofuran (250 mL) at 500C under an argon atmosphere was added dropwise a mixture of ethyl acetate (15.3 mL, 156 mmol) and ethyl diethoxyacetate (25 mL, 142 mmol) over 30 min. Upon complete addition the reaction was brought to reflux for 4 hours before allowing to cool to ambient temperature with continued stirring for an additional 16 hours. The mixture was concentrated to approximately one-third of the original volume by rotary evaporation before quenching by the rapid addition to aqueous acetic acid (approximately 145 mL, 15percent v/v) at 00C followed by extraction with diethyl ether (4 x 100 mL). The combined organic extracts were washed sequentially with water (1 x 20 mL), a saturated sodium carbonate aqueous solution (3 x 50 mL), water (2 x 20 mL), brine (1 x 30 mL), then dried over MgSO4 and concentrated in vacuo to afford the desired ethyl 4,4- diethoxy-3-oxobutanoate (Scheme 1, A) as a clear yellow oil as a 4:1 mixture of keto-enol tautomers (25.05 g, 81percent). 1H NMR (300 MHz, CDCl3) δ 1.22 - 1.30 (m, 9H), 3.53 - 3.76 (m, 5.6H), 4.19 (q, J= 7.6 Hz, 2H), 4.67 (s, 0.8H), 4.92 (s, 0.2H), 5.45 (s, 0.2H), 11.88 (s, 0.2H).
Reference: [1] Patent: WO2010/106016, 2010, A1, . Location in patent: Page/Page column 125-126
[2] European Journal of Organic Chemistry, 2013, # 19, p. 3965 - 3969
[3] Patent: WO2007/58582, 2007, A1, . Location in patent: Page/Page column 49-50
[4] Journal of Organic Chemistry, 1998, vol. 63, # 5, p. 1668 - 1675
[5] Journal of medicinal chemistry, 1963, vol. 6, p. 283 - 288
[6] Journal of the American Chemical Society, 1931, vol. 53, p. 1989,1991
[7] Journal of the Chemical Society, 1914, vol. 105, p. 2458
[8] Journal of the American Chemical Society, 1919, vol. 41, p. 812
[9] Journal of Medicinal Chemistry, 1998, vol. 41, # 20, p. 3793 - 3803
[10] Patent: US2007/155746, 2007, A1, . Location in patent: Page/Page column 14-15; 23
[11] Patent: US2007/155764, 2007, A1, . Location in patent: Page/Page column 77
[12] Patent: US2015/31673, 2015, A1, . Location in patent: Paragraph 0140; 0141
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