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[ CAS No. 881913-20-8 ] {[proInfo.proName]}

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Chemical Structure| 881913-20-8
Chemical Structure| 881913-20-8
Structure of 881913-20-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 881913-20-8 ]

CAS No. :881913-20-8 MDL No. :MFCD11045054
Formula : C16H13BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :HFXYUCJLQZCNPD-UHFFFAOYSA-N
M.W : 248.08 Pubchem ID :58881077
Synonyms :

Calculated chemistry of [ 881913-20-8 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 79.21
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.7
Log Po/w (WLOGP) : 2.19
Log Po/w (MLOGP) : 2.72
Log Po/w (SILICOS-IT) : 1.93
Consensus Log Po/w : 2.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.2
Solubility : 0.0156 mg/ml ; 0.0000631 mol/l
Class : Moderately soluble
Log S (Ali) : -4.24
Solubility : 0.0143 mg/ml ; 0.0000575 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.49
Solubility : 0.00081 mg/ml ; 0.00000327 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.19

Safety of [ 881913-20-8 ]

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

Application In Synthesis of [ 881913-20-8 ]

* 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 [ 881913-20-8 ]
  • Downstream synthetic route of [ 881913-20-8 ]

[ 881913-20-8 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 90-11-9 ]
  • [ 4612-28-6 ]
  • [ 881913-20-8 ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 2 h; 1,3PhenylDiboronAcid 1.99g (12mmol), 1- bromo-naphthalene 2.07g (10mmol), Pd (PPh3) 4 (0.58 g, 0.5mmol) and potassium carbonate (4.15g, 30mmol) and THF: H2O = 2: 1 solution to 100ml were dissolved was stirred for 2 hours under reflux at 80 . After this was added the organic layer was dried H2O40ml obtained by extraction three times with ethyl ether 40ml magnesium sulfate, and the solvent evaporatedObtained by purification of the residue by silica gel column chromatography to give the intermediate D-2 (1.74g, 70percent yield).
Reference: [1] Patent: KR2016/30001, 2016, A, . Location in patent: Paragraph 0368-0371
  • 2
  • [ 5419-55-6 ]
  • [ 881913-20-8 ]
YieldReaction ConditionsOperation in experiment
67% With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane; toluene (6)
Synthesis of Compound 2-6
Under an argon gas atmosphere, a mixture of 200.0 g (706.3 mmol) of 1-(3-bromophenyl) naphthalene and 2.1 L of dehydrated THF was cooled down to -60 degrees C., and added with 543 mL (847 mmol) of hexane solution of 1.56M n-butyllithium in drops while being stirred.
Then, the reaction mixture was stirred for two hours at -60 degree C.398.5 g (2.119 mol) of triisopropyl borate was dropped into the reaction solution at -60 degrees C. Subsequently, the reaction mixture was warmed up to room temperature, and stirred for 17 hours.
The reaction mixture was further added with solution of hydrochloric acid to be stirred for one hour at room temperature.
After the reaction, the reaction mixture was further added with toluene, so that aqueous phase thereof was eliminated.
After organic phase thereof was dried with magnesium sulfate, the solvent was distilled away under reduced pressure.
By recrystallizing the obtained solid by toluene, 126 g of 3-(1-naphthyl) phenylboronic acid was obtained at an yield of 67percent.
Reference: [1] Patent: US2009/8605, 2009, A1,
  • 3
  • [ 121-43-7 ]
  • [ 881913-20-8 ]
Reference: [1] Patent: EP2471772, 2012, A1, . Location in patent: Page/Page column 57
  • 4
  • [ 121-43-7 ]
  • [ 7732-18-5 ]
  • [ 881913-20-8 ]
YieldReaction ConditionsOperation in experiment
37 g
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h;
Stage #2: for 2 h;
Stage #3: With hydrogenchloride In tetrahydrofuran; hexane
1-Bromo-3-naphthylbenzene (20 g, 71 mmol) was dissolved in 250 ml of dehydrated THF. The solution was kept at -78 ° C. and 50 ml of 1.2 MR n-BuLi in hexane solution was added. After stirring for 1 hour, 25 ml of trimethyl borate was added and after stirring for 2 hours, The temperature was gradually raised. 1N HCl was added, 50 ml of methylene chloride was added and extracted, It was concentrated and dried. This operation was repeated twice to obtain 37 g of Compound 3.
Reference: [1] Patent: JP5750821, 2015, B2, . Location in patent: Paragraph 0165-0167
  • 5
  • [ 13922-41-3 ]
  • [ 881913-20-8 ]
Reference: [1] Patent: EP2471772, 2012, A1,
[2] Patent: JP5750821, 2015, B2,
  • 6
  • [ 591-18-4 ]
  • [ 881913-20-8 ]
Reference: [1] Patent: EP2471772, 2012, A1,
[2] Patent: JP5750821, 2015, B2,
  • 7
  • [ 881913-20-8 ]
  • [ 589-87-7 ]
  • [ 1268954-77-3 ]
Reference: [1] Patent: EP2471772, 2012, A1, . Location in patent: Page/Page column 57-58
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