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[ CAS No. 164461-18-1 ] {[proInfo.proName]}

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Chemical Structure| 164461-18-1
Chemical Structure| 164461-18-1
Structure of 164461-18-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 164461-18-1 ]

CAS No. :164461-18-1 MDL No. :MFCD04974062
Formula : C16H11BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :MWEKPLLMFXIZOC-UHFFFAOYSA-N
M.W : 246.07 Pubchem ID :5084102
Synonyms :

Calculated chemistry of [ 164461-18-1 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 79.97
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) : -5.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.94
Log Po/w (WLOGP) : 2.26
Log Po/w (MLOGP) : 2.65
Log Po/w (SILICOS-IT) : 2.11
Consensus Log Po/w : 2.19

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.4
Solubility : 0.00968 mg/ml ; 0.0000394 mol/l
Class : Moderately soluble
Log S (Ali) : -4.49
Solubility : 0.00797 mg/ml ; 0.0000324 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.48
Solubility : 0.000815 mg/ml ; 0.00000331 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.05

Safety of [ 164461-18-1 ]

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 [ 164461-18-1 ]

* 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 [ 164461-18-1 ]
  • Downstream synthetic route of [ 164461-18-1 ]

[ 164461-18-1 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 164461-18-1 ]
  • [ 298-12-4 ]
  • [ 3029-19-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 28, p. 8201 - 8205[2] Angew. Chem., 2017, vol. 129, # 28, p. 8313 - 8317,5
  • 2
  • [ 121-43-7 ]
  • [ 1714-29-0 ]
  • [ 164461-18-1 ]
YieldReaction ConditionsOperation in experiment
74%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h;
Stage #2: at -78 - 20℃; for 2 h;
To a round bottom flask1-Bromo-pyrene (30g, 107 mmol) was dissolved in 240 mL THF. In the cooling state up to -78 n-BuLi in n-hexane (1.6M) was put in a slow (80 mL). At the end of the addition and then stirred for about 1 hour at -78 was put trimethyl borate (15.5 g, 149 mmol). After 1 hour stirring at -78 stirred at room temperature for about two hours and put in a 2N HCl was adjusted to acidic. While the removal of the solvent after extraction with EA obtained with hexane to give the 1-pyreneboronic acid 19.5 g (yield 74 percent).
74% With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 3 h; 30 g (107 mmol) of 1-bromopyrene was dissolved in 240 mL of THF in a round bottom flask. The n-BuLi in n-hexane (1.6M) (80 mL) was slowly added to the solution while cooling to -78 ° C. After the addition, trimethylborate (15.5 g, 149 mmol) was added thereto at -78 ° C for about 1 hour. After stirring at -78 ° C for 1 hour, the mixture was stirred at room temperature for 2 hours and 2N HCl was added to adjust the acidity. The solvent was removed by extraction with EA, and crystals were obtained with hexane to obtain 19.5 g (yield: 74percent) of 1-pyrene boronic acid.
70%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 1 h; Inert atmosphere
Stage #2: at -78 - 20℃; for 24 h;
Stage #3: With hydrogenchloride In tetrahydrofuran; hexane for 1 h;
Synthesis of Pyren-1-ylboronic acid
An excess of 1.6 M n-BuLi in hexane (50 mL, 80 mmol) was added to a solution of 1-bromopyrene (20.4 g, 72.6 mmol) in 500 ml dry tetrahydrofuran at -78° C. under N2.
The reaction mixture was then maintained at 0° C. for 1 h before cooling to -78° C. Trimethyl borate (10.4 g, 100 mmol) was added dropwise; the solution was then warmed slowly to room temperature and stirred for 24 h. 2N HCl (150 ml) was added and then the mixture was stirred for a further 1 h.
The reaction mixture was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was evaporated in vacuo, and the residue was crystallized (n-hexane) to give the pyren-1-ylboronic acid 12.5 g as a yellow solid (70percent)
Reference: [1] Patent: KR101515814, 2015, B1, . Location in patent: Paragraph 0343; 0344
[2] Patent: KR101503771, 2015, B1, . Location in patent: Paragraph 0215; 0216
[3] Patent: US2014/131664, 2014, A1, . Location in patent: Paragraph 0025-0026
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1998, # 7, p. 1263 - 1268
[5] ChemPlusChem, 2013, vol. 78, # 10, p. 1288 - 1295
  • 3
  • [ 5419-55-6 ]
  • [ 1714-29-0 ]
  • [ 164461-18-1 ]
YieldReaction ConditionsOperation in experiment
72%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h;
1-Bromopyrene (1.0g, 3.56 mmol) was dissolved in anhydrousTHF solution (20 mL) and stirred at−78C. Then, 1.6Mn-BuLi (2.1 mL) was added.Triisopropyl borate (1.2 mL) was added to the reaction after 30 min. After the reactionwas finished, the solution was acidified with 2 N HCl solution at room temperature andextracted with ethyl acetate and water. The organic layer was dried with anhydrous MgSO4and filtered. The solution was evaporated. The residue was redissolved in hexane and addedto ethyl acetate. The precipitate was filtered and washed with hexane to obtain a beigecompound (0.63 g, 72percent). 1H-NMR (300 MHz, DMSO): δ(ppm) = 8.72-8.69 (d, 1H) 8.60 (s, 2H) 8.30-8.15 (m,7H) 8.06-8.04 (t, 1H).
68%
Stage #1: With n-butyllithium In tetrahydrofuran at -100℃; for 2 h; Inert atmosphere
Stage #2: for 4 h; Inert atmosphere
In the nitrogen,Clean and dry 1000ml three-mouth bottle,Add 1-bromoindole, THF,Cool down to -100°C,Butyllithium, plus complete, insulation 2h,Triisopropyl borate was added dropwise, incubated for 4 h, acidified with hydrochloric acid, washed with water, dehydrated with solvent, and beaten with toluene.Get 1 - deuterated boric acid;HPLC: 99.3percent, yield: 68percent;
60% With hydrogenchloride In tetrahydrofuran <Step 9> Synthesis of pyrene-1-boronic acid (Compound 1-13)
1-Bromopyrene (compound 1-12, 30 g) was dissolved in tetrahydrofuran (500 ml).
The reaction mixture was cooled to -78° C. and stirred for one hour while gradually adding an n-butyllithium solution (1.6N, 80 ml) thereto, and triisopropylborate (30 ml) was added thereto.
The reaction solution was gradually raised to room temperature and stirred at that temperature for 15 hours. 1N HCl (250 ml) was gradually added and an aqueous layer was removed.
The resultant organic layer was washed with a saturated ammonium chloride solution and a saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated.
The crude product was recrystallized from n-hexane to give a titled compound (15.7 g, yield 60.0percent) as a pale yellow solid.
51% With n-butyllithium In tetrahydrofuran at -78 - 20℃; Inert atmosphere 1-Bromo-pyrene 10 g was added to 500 mL round floorflask, melted in anhydrous tetrahydrofuran (THF) 120 mL, and agitated. After reaction temperature was set to −78 C,2.0 M n-Butyllithium 23.4 mL (50.59 mmol) was addedinto reaction mixture slowly. In 10 minutes, triisopropylborate 10 mL was added to reaction mixture. When reactiontemperature increased to room temperature in an hour,12 M HCl 7.2 mL was added. The reaction was completed,compound was extracted with ethyl acetate (EA)and water, and the organic layer was dried with anhydrousMgSO4 and filtered. After the compound was concentratedunder reduced pressure, white solid was obtained in 51percent.1H-NMR (300 MHz, THF-d8) (ppm): 8.89–8.85(m, 1H), 8.32–8.28 (m, 1H), 8.21–8.15 (m, 3H), 8.14–8.03(m, 3H), 8.01–7.94 (m, 1H), 7.10 (s, 2H).

Reference: [1] Molecular Crystals and Liquid Crystals, 2015, vol. 618, # 1, p. 47 - 54
[2] Patent: CN107652224, 2018, A, . Location in patent: Paragraph 0061; 0067; 0068
[3] Patent: US2011/57182, 2011, A1,
[4] Journal of Nanoscience and Nanotechnology, 2017, vol. 17, # 8, p. 5669 - 5672
  • 4
  • [ 1714-29-0 ]
  • [ 164461-18-1 ]
Reference: [1] Chemical Research in Toxicology, 2002, vol. 15, # 7, p. 964 - 971
[2] Journal of Physical Chemistry A, 2001, vol. 105, # 35, p. 8154 - 8161
[3] Angewandte Chemie - International Edition, 2002, vol. 41, # 16, p. 2978 - 2980
[4] Chemistry - A European Journal, 2002, vol. 8, # 21, p. 4877 - 4883
[5] Synlett, 2002, # 5, p. 687 - 691
[6] Journal of Physical Chemistry A, 2000, vol. 104, # 6, p. 1130 - 1140
[7] Organic Letters, 2009, vol. 11, # 17, p. 3850 - 3853
[8] Chemistry Letters, 2008, vol. 37, # 11, p. 1122 - 1123
[9] Journal of Nanoscience and Nanotechnology, 2010, vol. 10, # 8, p. 5153 - 5160
[10] Journal of the Chinese Chemical Society, 2012, vol. 59, # 3, p. 289 - 296
[11] Chemical Communications, 2016, vol. 52, # 62, p. 9679 - 9682
  • 5
  • [ 688-74-4 ]
  • [ 1714-29-0 ]
  • [ 164461-18-1 ]
Reference: [1] Patent: CN106749094, 2017, A, . Location in patent: Paragraph 0050; 0055
  • 6
  • [ 121-43-7 ]
  • [ 1714-29-0 ]
  • [ 1033995-63-9 ]
  • [ 164461-18-1 ]
Reference: [1] Angewandte Chemie - International Edition, 2002, vol. 41, # 16, p. 2978 - 2980
  • 7
  • [ 76-09-5 ]
  • [ 1714-29-0 ]
  • [ 164461-18-1 ]
  • [ 349666-24-6 ]
Reference: [1] European Journal of Organic Chemistry, 2001, # 20, p. 3819 - 3829
  • 8
  • [ 349666-24-6 ]
  • [ 164461-18-1 ]
Reference: [1] Chemical Communications, 2016, vol. 52, # 62, p. 9679 - 9682
  • 9
  • [ 1369381-75-8 ]
  • [ 164461-18-1 ]
Reference: [1] Journal of the Chinese Chemical Society, 2012, vol. 59, # 3, p. 289 - 296
  • 10
  • [ 129-00-0 ]
  • [ 164461-18-1 ]
Reference: [1] Journal of the Chinese Chemical Society, 2012, vol. 59, # 3, p. 289 - 296
[2] Chemical Communications, 2016, vol. 52, # 62, p. 9679 - 9682
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