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[ CAS No. 1161009-89-7 ] {[proInfo.proName]}

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Chemical Structure| 1161009-89-7
Chemical Structure| 1161009-89-7
Structure of 1161009-89-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1161009-89-7 ]

CAS No. :1161009-89-7 MDL No. :MFCD30187275
Formula : C31H27BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :GPTMWZAAIQOCLM-UHFFFAOYSA-N
M.W : 442.36 Pubchem ID :69676279
Synonyms :

Calculated chemistry of [ 1161009-89-7 ]

Physicochemical Properties

Num. heavy atoms : 34
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.23
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 139.22
TPSA : 18.46 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 7.36
Log Po/w (WLOGP) : 6.33
Log Po/w (MLOGP) : 5.27
Log Po/w (SILICOS-IT) : 6.49
Consensus Log Po/w : 5.09

Druglikeness

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

Water Solubility

Log S (ESOL) : -7.68
Solubility : 0.00000933 mg/ml ; 0.0000000211 mol/l
Class : Poorly soluble
Log S (Ali) : -7.58
Solubility : 0.0000117 mg/ml ; 0.0000000265 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -11.68
Solubility : 0.0000000009 mg/ml ; 0.0 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 5.05

Safety of [ 1161009-89-7 ]

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 [ 1161009-89-7 ]

* 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 [ 1161009-89-7 ]
  • Downstream synthetic route of [ 1161009-89-7 ]

[ 1161009-89-7 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 1161009-88-6 ]
  • [ 73183-34-3 ]
  • [ 1161009-89-7 ]
YieldReaction ConditionsOperation in experiment
96% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In toluene for 16 h; Reflux a Synthesis of 4-bromos iro-9,9'-bifluorene ( -1) 60 g (152 mmol) 4-bromospiro-9,9'-bifluorene, 47.2 g (182.1 mmol) bis- pinacolatediboron, 3.72 g (4.55 mmol) 1,1'-bis(diphenylphosphino)- ferrocene-palladium(ll)dichloride dichloromethane complex, 44.7 (455 mmol) potassium acetate and 600 ml of toluene is heated under reflux for 16 h. After cooling, 200 ml of water are added, the mixture is stirred for a further 30 min., the organic phase is separated off, filtered through a short Celite bed, and the solvent is then removed in vacuum. The residue is recrystallised several times from heptanes/toluene. Yield: 67.1g, 96percent.
82.1% With potassium acetate In 1,4-dioxane at 100℃; for 12 h; Inert atmosphere Synthesis of Compound 02; The following reagents:dioxane: 140 mL,Compound 01: 7.00 g (17.7 mmol) ,bispinacolatodiboron : 6.75 g (26.6 mmol),potassium acetate: 3.47 g (35.4 mmol), andbis (triphenylphosphine ) palladium ( II ) dichloride: 621 mg(0.885 mmol)were put in a reaction vessel. The reaction solution was stirred at 100°C for 12 hr under a nitrogen atmosphere. It was confirmed by thin layer chromatography that the raw materials disappeared, and instead, a new compound was produced.[0103] The reaction solution was cooled to roomtemperature and was then concentrated under reduced pressure, followed by purification by silica gel column chromatography (eluent: toluene/heptane=l : 1 ) . The target fraction was concentrated, followed by extraction with methanol to obtain 6.43 g (14.5 mmol, yield: 82.1percent) of Compound 02. Theresulting compound was detected as a peak at m/z = 442 by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) to confirm being the target compound .
Reference: [1] Patent: WO2016/78738, 2016, A1, . Location in patent: Page/Page column 66
[2] Patent: WO2012/56919, 2012, A1, . Location in patent: Page/Page column 35; 37
[3] Patent: CN108658932, 2018, A, . Location in patent: Paragraph 0066; 0067; 0068
  • 2
  • [ 61676-62-8 ]
  • [ 1161009-88-6 ]
  • [ 1161009-89-7 ]
YieldReaction ConditionsOperation in experiment
73%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h;
Stage #2: at -78 - 20℃; for 12 h;
4-Bromo-9,9'-spirobifluorene (2.5 g, 6.4 mmol) was dissolved in 90 mL of anhydrous THF solution and cooled to -78 °C. Then, 2 M n-BuLi (7 mL,14 mmol) was dropped slowly. After stirring at -78 °C for 30 min, 2-isopropoxy-4,4',5,5'-tetramethyl-[1-3]dioxaborolane (2.75 mL, 14 mmol) was added in one portion. The resulting mixture was stirred for another 12 h and gradually warmed to room temperature. The reaction was quenched with water and extracted with ethyl acetate and water. The organic layer was dried with anhydrous MgSO4 and filtered. The solution was evaporated. Then, the residue was purified by recrystallized from chloroform/ethanolto give a white powder. (2.08 g, Yield 73percent) 1H NMR (300 MHz,DMSO): δ (ppm) 8.72-8.74 (d, 1H), 7.68-7.73 (t, 3H), 7.17-7.25 (q,3H), 6.92-6.97 (t, 4H), 6.56-6.66 (m, 4H), 1.32-1.39 (d, 12H).
Reference: [1] Dyes and Pigments, 2017, vol. 136, p. 255 - 261
[2] Organic Letters, 2009, vol. 11, # 12, p. 2607 - 2610
  • 3
  • [ 1161009-88-6 ]
  • [ 25015-63-8 ]
  • [ 1161009-89-7 ]
Reference: [1] Patent: CN108689972, 2018, A, . Location in patent: Paragraph 0060; 0068; 0069
  • 4
  • [ 4269-17-4 ]
  • [ 1161009-89-7 ]
Reference: [1] Patent: WO2012/56919, 2012, A1,
[2] Patent: CN108658932, 2018, A,
[3] Patent: CN108689972, 2018, A,
  • 5
  • [ 2052-07-5 ]
  • [ 1161009-89-7 ]
Reference: [1] Patent: WO2012/56919, 2012, A1,
[2] Patent: CN108658932, 2018, A,
  • 6
  • [ 121772-84-7 ]
  • [ 1161009-89-7 ]
Reference: [1] Patent: CN108658932, 2018, A,
[2] Patent: CN108689972, 2018, A,
  • 7
  • [ 98-80-6 ]
  • [ 1161009-89-7 ]
Reference: [1] Patent: CN108658932, 2018, A,
[2] Patent: CN108689972, 2018, A,
  • 8
  • [ 13029-09-9 ]
  • [ 1161009-89-7 ]
Reference: [1] Dyes and Pigments, 2017, vol. 136, p. 255 - 261
  • 9
  • [ 583-53-9 ]
  • [ 1161009-89-7 ]
Reference: [1] Dyes and Pigments, 2017, vol. 136, p. 255 - 261
  • 10
  • [ 55365-18-9 ]
  • [ 1161009-89-7 ]
Reference: [1] Patent: CN108658932, 2018, A,
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