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[ CAS No. 1035690-24-4 ] {[proInfo.proName]}

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Chemical Structure| 1035690-24-4
Chemical Structure| 1035690-24-4
Structure of 1035690-24-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1035690-24-4 ]

CAS No. :1035690-24-4 MDL No. :MFCD16994464
Formula : C15H21BO3 Boiling Point : -
Linear Structure Formula :- InChI Key :QRRJFVBHNJSHKB-UHFFFAOYSA-N
M.W : 260.14 Pubchem ID :57467635
Synonyms :

Calculated chemistry of [ 1035690-24-4 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.6
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 76.91
TPSA : 27.69 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.45 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.43
Log Po/w (WLOGP) : 2.46
Log Po/w (MLOGP) : 1.92
Log Po/w (SILICOS-IT) : 2.36
Consensus Log Po/w : 2.04

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.65
Solubility : 0.0583 mg/ml ; 0.000224 mol/l
Class : Soluble
Log S (Ali) : -3.69
Solubility : 0.0529 mg/ml ; 0.000203 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.34
Solubility : 0.0119 mg/ml ; 0.0000458 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.15

Safety of [ 1035690-24-4 ]

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 [ 1035690-24-4 ]

* 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.

  • Downstream synthetic route of [ 1035690-24-4 ]

[ 1035690-24-4 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 1035690-22-2 ]
  • [ 73183-34-3 ]
  • [ 1035690-24-4 ]
YieldReaction ConditionsOperation in experiment
55% With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 100℃; for 3h; INTERMEDIATE 37 2-(3-cyclopropoxyphenyl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane; A mixture of intermediate 36 (2.87g, 10.9mmol), bis(pinacolato)diboron (4.16g, 16.4mmol) and potassium acetate (3.2g, 32.7mmol) in anhydrous dioxane, was stirred under nitrogen atmosphere and then PdCl2dppf.CH2CI2 (0.5g, 0.55mmol) was added. The reaction mixture was heated at 1000C for 3h. The crude was then filtered over celite, washed with dioxane and evaporated under reduce pressure. The residue obtained was purified by reverse-phase chromatography eluting with a gradient of water and AcN/MeOH (1/1 ) (from 0% to 100% of AcN/MeOH(1/1 )). The desired product was obtained as a yellow oil. Yield=55%. LRMS: m/z 261 (M+1 )+. Retention time: 7.23 min
41% With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 100℃; for 21h;Inert atmosphere; 2-(3-(Cyclopropyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2- dioxaborolane (T24.2). A stirred mixture of T24.1 (0.144 g, 0.676 mmol), bis(pinacolato)diboron (0.189 g, 0.745 mmol), potassium acetate (0.2007 g, 2.04 mmol), and dichloro[l ,r-bis(diphenylphosphino)ferrocene]palladium (II) DCM adduct (25.3 mg, 0.0346 mmol) in dry 1,4-dioxane (3.0 mL) was purged three times with argon and placed under vacuum three times. The mixture was heated to 100C, and monitored with LC-MS and TLC. After 21 hours, the reaction was cooled to room temperature and filtered through Celite filter aid. The organic solvent was removed under reduced pressure. The residue was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford T24.2 as a colorless oil (72 mg, 41% yield). 1H NMR (400 MHz, CDCl3) delta ppm 7.51 (1 H, d, J=2.7 Hz), 7.44 (1 H, d, J=7.0 Hz), 7.34 (1 H, m), 7.14 (1 H, dd, J=7.6, 2.2 Hz), 3.80 (1 H, ddd, J=8.8, 5.9, 3.3 Hz), 1.36 (12 H, s), 0.82 (4 H, m).
  • 2
  • [ 1035690-24-4 ]
  • [ 1142224-89-2 ]
  • [ 1142227-97-1 ]
YieldReaction ConditionsOperation in experiment
98% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 23 - 90℃; for 19h;Inert atmosphere; Methyl 3'-(cyclopropyloxy)-2-(2,2-dimethylcyclopentyI)-l,l'- biphenyl-4-carboxylate (T24.3). To a stirred solution of T7.6F (438.2 mg, 1.15 mmol) in dry DMF (5.0 mL) at 23C was added potassium carbonate (480.3 mg, 3.47 mmol) followed by tetrakis(triphenylphosphine)palladium (140.2 mg, 0.121 mmol). The mixture was purged three times with argon and placed under vacuum three times. Before heating, T24.2 ( 523.1 mg, 2.01 mmol) was added via syringe and then the mixture was heated to 90C. After 19 hours, LCMS showed reaction was complete. The mixture was cooled to room temperature and then diluted with water. After extracting three times with EtOAc, the mixture was concentrated in vacuo and then purified on silica gel (0%-10% EtOAc/hexane) to afford T24.3 as a colorless oil that was used without further purification (411.5 mg, 98% yield). MS ESI (pos.) m/e: 365.0 (M+H)+.
YieldReaction ConditionsOperation in experiment
With potassium phosphate; at 70 - 100℃;Inert atmosphere; General procedure: General Procedure D: Preparation of Coupled Aryl and Heteroaryl Groups Using Suzuki Catalyzed Coupling Conditions Between an Organoboronic Acid or Ester and an Aryl Halide or Heteroaryl Halide (0329) [00218] A suspension of heteroaryl chloride (1 equivalent), organoboronic acid or organoboronic ester (1.2 equivalents), K3PO4 (3.0 equivalents) and Pd(dppf)Cl2?DCM (5 mol%) or Pd2(dba)3 (10 mol%) in DME or 1,4-dioxane (40 mL/mmol) was stirred at 70-100 oC for 2-6 hours under N2. Then, the reaction mixture was quenched with water (30 mL/mmol) and resulting mixture extracted with EtOAc (30 mL/mmol x 3). The organic phases were washed with water (30 mL/mmol) and brine (30 mL/mmol), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo, and the resulting residue was purified by silica gel column chromatography to afford the coupled ring system.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃; for 16h; General procedure: A mixture of Compound 27B (1.35 g, 5.4mmol), Pd(dppf)C12 (0.35 g, 0.43 mmol), 4,4,4,4,5,5,5?, 5?-octamethyl-2,2?-bi( 1,3 ,2-dioxaborolane) (2.09 g, 8.22 mmol), and potassium acetate (1.62 g, 16.5 mmol) in 1,4-dioxane (50 ml) was heated at 80C for 16 hours. The mixture was diluted with water (200 mL) and extracted with ethyl acetate (200 mL x 2). The combined extracts were washed with water (200 mL) and brine (200 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, from 0% to 10% v/v) to furnish Compound 27C. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used.
  • 4
  • [ 1035690-24-4 ]
  • [ 1142224-89-2 ]
  • [ 1142227-99-3 ]
  • 6
  • [ 1035690-24-4 ]
  • 3-bromo-5-(1-methyl-1H-pyrazol-4-yl)furo[3,2-b]pyridine [ No CAS ]
  • 3-(3-cyclopropoxyphenyl)-5-(1-methyl-1H-pyrazol-4-yl)furo[3,2-b]pyridine [ No CAS ]
  • 7
  • [ 923595-58-8 ]
  • [ 1035690-24-4 ]
  • [ 761446-44-0 ]
  • 3-(3-cyclopropoxyphenyl)-5-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine [ No CAS ]
  • 8
  • [ 1035690-24-4 ]
  • C14H10F3N3O4S [ No CAS ]
  • 6-(3-cyclopropoxyphenyl)-2-(pyridin-2-yl)-7,8-dihydrophthalazin-1(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
48.78% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; at 70℃; for 3h;Inert atmosphere; General procedure: According to scheme 2, step viii: A mixture of intermediate 15a (200.00 mg, 518.07 umol, 1.00 eq), (2-methoxyphenyl)-boronic acid (157.45 mg, 1.04 mmol, 2.00 eq), Pd(PPh3)4 (119.73 mg, 103.61 umol, 0.20 eq), Na2CO3 (2 M, 1.17 mL, 4.50 eq) in THF (4.00 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 70C for 3 hours under N2 atmosphere. The mixture was added water(20mL), extracted with AcOEt (20mLx3), the organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by prep-TLC (PE:EA=0:1) to give intermediate 16a (190.00 mg, crude) as a yellow oil.
  • 9
  • [ 1035690-24-4 ]
  • 1-oxo-2-(pyrimidin-2-yl)-1,2,7,8-tetrahydrophthalazin-6-yl trifluoromethanesulfonate [ No CAS ]
  • 6-(3-cyclopropoxyphenyl)-2-(pyrimidin-2-yl)-7,8-dihydrophthalazin-1(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; at 70℃; for 3h;Inert atmosphere; General procedure: According to scheme 2, step viii: A mixture of intermediate 15a (200.00 mg, 518.07 umol, 1.00 eq), (2-methoxyphenyl)-boronic acid (157.45 mg, 1.04 mmol, 2.00 eq), Pd(PPh3)4 (119.73 mg, 103.61 umol, 0.20 eq), Na2CO3 (2 M, 1.17 mL, 4.50 eq) in THF (4.00 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 70C for 3 hours under N2 atmosphere. The mixture was added water(20mL), extracted with AcOEt (20mLx3), the organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by prep-TLC (PE:EA=0:1) to give intermediate 16a (190.00 mg, crude) as a yellow oil.
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