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[ CAS No. 1006-68-4 ] {[proInfo.proName]}

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Chemical Structure| 1006-68-4
Chemical Structure| 1006-68-4
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Product Details of [ 1006-68-4 ]

CAS No. :1006-68-4 MDL No. :MFCD00067074
Formula : C9H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :YPYPBEGIASEWKA-UHFFFAOYSA-N
M.W : 145.16 Pubchem ID :589311
Synonyms :

Calculated chemistry of [ 1006-68-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.94
TPSA : 26.03 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.94
Log Po/w (XLOGP3) : 2.0
Log Po/w (WLOGP) : 2.34
Log Po/w (MLOGP) : 1.06
Log Po/w (SILICOS-IT) : 2.52
Consensus Log Po/w : 1.97

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.67
Solubility : 0.308 mg/ml ; 0.00212 mol/l
Class : Soluble
Log S (Ali) : -2.17
Solubility : 0.974 mg/ml ; 0.00671 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.73
Solubility : 0.0269 mg/ml ; 0.000185 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.14

Safety of [ 1006-68-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1006-68-4 ]

* 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 [ 1006-68-4 ]
  • Downstream synthetic route of [ 1006-68-4 ]

[ 1006-68-4 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 1006-68-4 ]
  • [ 62124-43-0 ]
YieldReaction ConditionsOperation in experiment
90.9%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h;
Stage #2: With hexachloroethane In tetrahydrofuran at 25℃; for 12 h;
[0819] to a solution of 5-phenyloxazole (800 mg, 5.51 mmol) in THF (10 ml) was added n-BuLi (2.5 m, 2.76 ml) drop-wise at -78 °C and stirred for 30 min, then hexachloroethane (1.96 g, 8.27 mmol) in THF (2 ml) was added, the reaction mixture was slowly warmed to 25 °C and stirred for 12 h. The mixture was poured into ice- water (20 ml) and extracted ethyl acetate (10 ml x 2), the organic phases were washed with brine (10 ml), dried over Na2SO4, filtered and concentrated, the residue was purified by silica gel column (petroleum ether: ethyl acetate = 10: 1) to give 114a (900 mg, yield: 90.9percent) as yellow oil. 1H NMR (400mhz, CDCl3) δ 7.58 (d, = 7.3 hz, 2h), 7.45 - 7.38 (m, 2h), 7.38 - 7.31 (m, 1h), 7.27 (s, 1h).
49%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.25 h;
Stage #2: With hexachloroethane In tetrahydrofuran at -78 - 20℃; for 2 h;
[00208] To a round bottom flask was added 5-phenyloxazole (1.0 gm, 6.89 mmol) and THF (10 mL). The reaction was cooled to -78 °C. Then 2.5 M nBuLi (3.03 mL, 7.58 mmol) was added to the reaction at -78 °C. The reaction turned to deep red color. After 15 min, hexachloroethane (1.170 mL, 10.33 mmol) was added at -78 °C. The reaction was slowly warmed to rt over 2 hrs and then was poured onto ice. The resulting solution was extracted with EtO Ac (2 x 30ml). The combined EtO Ac layers were washed with saturated aqueous NaCl, dried over MgS04, filtered and concentrated. The resulting residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-100percent EtO Ac/Hex to give the product, 2-chloro-5-phenyloxazole, (600 mg, 3.34 mmol, 49 percent yield) as a light pale liquid. Anal. Calcd. for C9H6C1N0 m/z 179.1, found: 180.1 (M+H)+; 'H NMR (500 MHz, CDC13) δ ppm 7.60 (d, J=7.15 Hz, 2 H), 7.43 (t, J=7.42 Hz, 2 H), 7.38 - 7.33 (m, 1 H), 7.29 (s, 1 H); 13C NMR (126 MHz, CDCl3) 5 ppm 153.78, 146.16, 129.01, 126.93, 124.03, 123.31.
Reference: [1] Organic Letters, 2005, vol. 7, # 15, p. 3351 - 3354
[2] Patent: WO2018/64119, 2018, A1, . Location in patent: Paragraph 0819
[3] Patent: WO2013/12827, 2013, A1, . Location in patent: Paragraph 00208
[4] Journal of Organic Chemistry, 1996, vol. 61, # 16, p. 5192 - 5193
  • 2
  • [ 1006-68-4 ]
  • [ 740806-67-1 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 8, p. 3303 - 3306
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