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[ CAS No. 144104-59-6 ] {[proInfo.proName]}

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Chemical Structure| 144104-59-6
Chemical Structure| 144104-59-6
Structure of 144104-59-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 144104-59-6 ]

CAS No. :144104-59-6 MDL No. :MFCD01319013
Formula : C8H8BNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :VHADYSUJZAPXOW-UHFFFAOYSA-N
M.W : 160.97 Pubchem ID :2734361
Synonyms :

Calculated chemistry of [ 144104-59-6 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 3.0
Molar Refractivity : 48.12
TPSA : 56.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.95
Log Po/w (WLOGP) : -0.15
Log Po/w (MLOGP) : -0.24
Log Po/w (SILICOS-IT) : -0.09
Consensus Log Po/w : 0.09

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.93
Solubility : 1.91 mg/ml ; 0.0119 mol/l
Class : Very soluble
Log S (Ali) : -1.72
Solubility : 3.08 mg/ml ; 0.0191 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.16
Solubility : 1.11 mg/ml ; 0.00687 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.7

Safety of [ 144104-59-6 ]

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 [ 144104-59-6 ]

* 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 [ 144104-59-6 ]
  • Downstream synthetic route of [ 144104-59-6 ]

[ 144104-59-6 ] Synthesis Path-Upstream   1~7

  • 1
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YieldReaction ConditionsOperation in experiment
25%
Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 0.25 h; Inert atmosphere
Stage #2: With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.166667 h; Inert atmosphere
Stage #3: at 0 - 20℃; Inert atmosphere
A dry and nitrogen-flushed three-necked flask, equipped with a magnetic stirrer and a septum, was charged with NaH (1.02 g, 42.5 mmol) in dry THF (80 mL). The 5-bromoindole (5.0 g, 25.5 mmol) was added dropwise to the solution under an N2 atmosphere at 0 °C, and the reaction mixture was stirred for 15 min. After that the n-BuLi (2.5 M in hexane, 15 mL, 37.5 mmol) was slowly added to the reaction mixture, and then the mixture was stirred for 10 mins. Next the triisopropyl borate (22 mL, 51 mmol) was added dropwise to the mixture. When the addition was complete, the mixture was warmed to room temperature overnight and stirred for 2 hours. The reaction mixture was quenched with saturated NH4Cl and stirred for 30 min. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layer was washed with water and brine, and dried over Na2SO4. After completely removing the solvent, the residue was treated with EtOAc/petroleum ether and filtered to afford 1H-indol-5-ylboronic acid (b1) as colorless solid (1.02 g, 25percent yield). 2 1H-NMR (DMSO-d6) δ 11.1 (s, 1H), 8.30 (s, 1H), 7.81 (d, 1H, J=8.1 Hz), 7.47 (d, 1H, J=8.1 Hz), 7.34 (s, 1H).13C-NMR (100 MHz, (DMSO-d6) δ 138.0, 128.0, 127.5, 127.4, 127.3, 125.4, 111.0, 102.0.
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 1, p. 35 - 42
  • 2
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Reference: [1] Patent: WO2006/51851, 2006, A1, . Location in patent: Page/Page column 71-72
[2] Journal of Organic Chemistry, 2004, vol. 69, # 20, p. 6812 - 6820
[3] Journal of Organic Chemistry, 2007, vol. 72, # 3, p. 1047 - 1050
[4] Organic Letters, 2012, vol. 14, # 18, p. 4814 - 4817,4
[5] Journal of Organic Chemistry, 2013, vol. 78, # 13, p. 6427 - 6439
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Reference: [1] Patent: US6307056, 2001, B1,
  • 4
  • [ 10075-50-0 ]
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  • [ 144104-59-6 ]
Reference: [1] Patent: EP1820799, 2007, A1,
  • 5
  • [ 10075-50-0 ]
  • [ 13675-18-8 ]
  • [ 144104-59-6 ]
Reference: [1] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1859 - 1863
  • 6
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  • [ 100846-24-0 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 14, p. 4300 - 4302
  • 7
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  • [ 269410-24-4 ]
Reference: [1] Patent: WO2015/106292, 2015, A1, . Location in patent: Paragraph 00729; 00740; 00741
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