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[ CAS No. 107834-03-7 ] {[proInfo.proName]}

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Chemical Structure| 107834-03-7
Chemical Structure| 107834-03-7
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Product Details of [ 107834-03-7 ]

CAS No. :107834-03-7 MDL No. :MFCD02682003
Formula : C11H8OS Boiling Point : -
Linear Structure Formula :- InChI Key :UECDQUOWFRTJOH-UHFFFAOYSA-N
M.W :188.25 Pubchem ID :736499
Synonyms :

Calculated chemistry of [ 107834-03-7 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.14
TPSA : 45.31 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.06
Log Po/w (XLOGP3) : 3.2
Log Po/w (WLOGP) : 3.23
Log Po/w (MLOGP) : 2.09
Log Po/w (SILICOS-IT) : 4.36
Consensus Log Po/w : 2.99

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.52
Solubility : 0.0572 mg/ml ; 0.000304 mol/l
Class : Soluble
Log S (Ali) : -3.82
Solubility : 0.0283 mg/ml ; 0.00015 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.13
Solubility : 0.0138 mg/ml ; 0.0000735 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.83

Safety of [ 107834-03-7 ]

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

Application In Synthesis of [ 107834-03-7 ]

* 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 [ 107834-03-7 ]
  • Downstream synthetic route of [ 107834-03-7 ]

[ 107834-03-7 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 1003-09-4 ]
  • [ 87199-17-5 ]
  • [ 107834-03-7 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With potassium carbonate In N,N-dimethyl-formamide for 0.5 h; Inert atmosphere
Stage #2: With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 90℃; for 6 h; Inert atmosphere
2-bromothiophene (0.489 g, 3 mmol),4-formylphenylboronic acid (0.60 g, 4 mmol), K2CO3 (0.696 g, 1 N) and N,N-dimethylformamide (20 mL) were placed in a 100 mL three-neck flask. After mixing for 30 minutes under N2 protection, tetrakis(triphenylphosphine)palladium (0.115 g, 0.1 mmol) was added.The reaction was stirred at 90 ° C for 6 hours. It was naturally cooled to ambient temperature, and the crude product was dissolved in dichloromethane and washed with water (100ml). The organic solution was dried over MgSO 4 to remove water. The final product was recrystallized from ethyl acetate. Obtained a yellow solid of 0.46 g.The yield was 89percent.
87%
Stage #1: With palladium diacetate; triphenylphosphine In toluene at 20℃; for 0.166667 h; Inert atmosphere
Stage #2: With sodium carbonate In methanol; toluene at 110℃; for 3 h; Inert atmosphere
General procedure: A solution of Pd(OAc)2 (0.05 eq.) and PPh3 (0.2 eq.) in toluene was stirred at r.t. under an argonatmosphere for 10 mins. After that, the solution of an appropriate aryl-bromide (1 eq.), an appropriatearylboronic acid (1.1 eq.) and 2M aq. Na2CO3 (2 eq.) in MeOH and toluene was added. The mixturewas stirred at 110 °C under an argon atmosphere for 3 h. The reaction work up method is provided foreach compound.
Reference: [1] Patent: CN108586438, 2018, A, . Location in patent: Paragraph 0040; 0056-0058; 0062
[2] Molecules, 2017, vol. 22, # 3,
[3] Organic Letters, 2017, vol. 19, # 7, p. 1610 - 1613
[4] Patent: KR2017/124005, 2017, A, . Location in patent: Paragraph 0206
  • 2
  • [ 6165-68-0 ]
  • [ 1122-91-4 ]
  • [ 107834-03-7 ]
YieldReaction ConditionsOperation in experiment
87% With C7H10N2*Pd(2+)*2Cl(1-); potassium carbonate In ethanol; water for 0.166667 h; Reflux; Schlenk technique General procedure: A 20mL Schlenk tube with a magnetic stir bar was charged with aryl halide (2mmol), arylboronic acid (2.4mmol), K2CO3 (5mmol), 10mL of solvent [H2O, H2O–MeOH (1:1), H2O–EtOH (1:1), H2O–EG (1:1)] and an aliquot of 0.01M solution of palladium complexes PdCl2(L)2 or Pd[(L)4]Cl2 in MeOH (0.001–0.2molpercent) under air atmosphere. The reaction mixture was placed in a preheated oil bath: at 100°C for MeOH–H2O, at 110°C for EtOH–H2O, at 140°C for H2O and at 160°C for EG–H2O; and stirred under reflux for the given time. After this time, the mixture was cooled, acidified by 5M HCl (in the case of acids) and diluted with 10mL of H2O and 10mL of Et2O (or EtOAc). The organic phase was separated, and the aqueous layer was extracted with Et2O EtOAc) (2×10mL). The combined organic layers were washed with H2O (10mL), brine (10mL), and dried over Na2SO4. The pure products were obtained by a simple filtration of ether solution through silica gel pad and evaporation of a solvent.
40% With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In ethanol; water; tolueneReflux General procedure: Tetrakis(triphenylphosphine)palladium(0) (0.0168 mmol) was added to a solution of 4-bromobenzaldehyde (50, 5.6 mmol) in ethanol-toluene (40 mL, 1:1). After 15 min, the appropriate boronic acid 51b-m (6.75 mmol) was added, followed by sodium hydrogen carbonate (22.4 mmol) and water (11 mL). The resulting mixture was heated under reflux for 9-15 hours. After cooling, the reaction mixture was filtered through Celite.(R)., the organic phase was separated, washed with brine (2x20 mL), dried and the solvent evaporated in vacuo. The residue thus obtained was purified by flash-chromatography. Elution by light petroleum-ethyl acetate mixtures afforded the desired compounds.
Reference: [1] Chemistry of Heterocyclic Compounds, 2014, vol. 50, # 1, p. 19 - 25[2] Khim. Geterotsikl. Soedin., 2014, vol. 50, # 1, p. 24 - 31,7
[3] Russian Journal of General Chemistry, 2014, vol. 84, # 9, p. 1782 - 1792[4] Zh. Obshch. Khim., 2014, vol. 84, # 9, p. 1546 - 1556,11
[5] RSC Advances, 2015, vol. 5, # 85, p. 69776 - 69781
[6] Journal of Medicinal Chemistry, 2003, vol. 46, # 10, p. 1918 - 1930
[7] Catalysis Communications, 2016, vol. 79, p. 17 - 20
[8] European Journal of Organic Chemistry, 2006, # 17, p. 3938 - 3946
[9] Macromolecules, 2011, vol. 44, # 13, p. 5155 - 5167
[10] Journal of Medicinal Chemistry, 2018, vol. 61, # 14, p. 6379 - 6397
[11] Advanced Synthesis and Catalysis, 2008, vol. 350, # 14-15, p. 2391 - 2400
[12] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 11, p. 3429 - 3445
[13] Journal of Medicinal Chemistry, 2014, vol. 57, # 20, p. 8445 - 8458
[14] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 453 - 462
  • 3
  • [ 96-43-5 ]
  • [ 87199-17-5 ]
  • [ 107834-03-7 ]
YieldReaction ConditionsOperation in experiment
87% With C27H39Br2N3Pd; potassium hydroxide In isopropyl alcohol at 82℃; for 0.166667 h; General procedure: A two-necked 25.0mL flask fitted with a reflux condenser and septum was charged with aryl halide (1.0mmol), phenylboronic acid (1.2mmol), KOH (2.0mmol), diethyleneglycol-di-n-butylether (0.6mmol, internal standard), and the palladium-pyridine catalyst (0.01mol percent) in isopropyl alcohol (1.0mL) was added. The mixture was heated to 82°C under an air atmosphere. The conversion was monitored by gas chromatography.
Reference: [1] European Journal of Organic Chemistry, 2012, # 31, p. 6248 - 6259,12
[2] European Journal of Organic Chemistry, 2012, # 31, p. 6248 - 6259
[3] Tetrahedron, 2018, vol. 74, # 47, p. 6829 - 6838
  • 4
  • [ 188290-36-0 ]
  • [ 1122-91-4 ]
  • [ 107834-03-7 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 19, p. 8138 - 8142
[2] Synthetic Communications, 2011, vol. 41, # 23, p. 3524 - 3531
[3] European Journal of Organic Chemistry, 2017, vol. 2017, # 1, p. 111 - 123
[4] Heterocycles, 1990, vol. 31, # 11, p. 1951 - 1958
  • 5
  • [ 81443-44-9 ]
  • [ 107834-03-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 13, p. 2390 - 2410
[2] Bulletin of the Chemical Society of Japan, 2007, vol. 80, # 8, p. 1580 - 1586
  • 6
  • [ 14221-01-3 ]
  • [ 1122-91-4 ]
  • [ 107834-03-7 ]
Reference: [1] Patent: US5849911, 1998, A,
  • 7
  • [ 1264696-96-9 ]
  • [ 1122-91-4 ]
  • [ 107834-03-7 ]
Reference: [1] European Journal of Organic Chemistry, 2011, # 1, p. 143 - 149
  • 8
  • [ 5713-61-1 ]
  • [ 107834-03-7 ]
Reference: [1] Chemical Communications, 2015, vol. 51, # 22, p. 4656 - 4658
  • 9
  • [ 54663-78-4 ]
  • [ 1122-91-4 ]
  • [ 107834-03-7 ]
Reference: [1] Journal of Materials Chemistry A, 2013, vol. 1, # 38, p. 11909 - 11921
  • 10
  • [ 188290-36-0 ]
  • [ 87199-17-5 ]
  • [ 107834-03-7 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 2, p. 578 - 580
  • 11
  • [ 3437-95-4 ]
  • [ 1122-91-4 ]
  • [ 107834-03-7 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 20, p. 3909 - 3912
  • 12
  • [ 873-75-6 ]
  • [ 107834-03-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 13, p. 2390 - 2410
  • 13
  • [ 3437-95-4 ]
  • [ 87199-17-5 ]
  • [ 107834-03-7 ]
Reference: [1] European Journal of Organic Chemistry, 2012, # 13, p. 2635 - 2642
  • 14
  • [ 5676-81-3 ]
  • [ 5713-61-1 ]
  • [ 107834-03-7 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 3, p. 1291 - 1300
  • 15
  • [ 6165-68-0 ]
  • [ 107834-03-7 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 24, p. 4179 - 4182
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