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[ CAS No. 157869-15-3 ] {[proInfo.proName]}

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Chemical Structure| 157869-15-3
Chemical Structure| 157869-15-3
Structure of 157869-15-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 157869-15-3 ]

CAS No. :157869-15-3 MDL No. :MFCD00168852
Formula : C15H13NO Boiling Point : -
Linear Structure Formula :- InChI Key :YAXVIURCVHCTST-UHFFFAOYSA-N
M.W : 223.27 Pubchem ID :10878779
Synonyms :

Calculated chemistry of [ 157869-15-3 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.07
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 69.76
TPSA : 35.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.79
Log Po/w (XLOGP3) : 3.23
Log Po/w (WLOGP) : 2.76
Log Po/w (MLOGP) : 3.13
Log Po/w (SILICOS-IT) : 3.19
Consensus Log Po/w : 3.02

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.72
Solubility : 0.043 mg/ml ; 0.000193 mol/l
Class : Soluble
Log S (Ali) : -3.64
Solubility : 0.0508 mg/ml ; 0.000227 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.77
Solubility : 0.00377 mg/ml ; 0.0000169 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.1

Safety of [ 157869-15-3 ]

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 [ 157869-15-3 ]

* 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 [ 157869-15-3 ]
  • Downstream synthetic route of [ 157869-15-3 ]

[ 157869-15-3 ] Synthesis Path-Upstream   1~9

  • 1
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YieldReaction ConditionsOperation in experiment
93%
Stage #1: With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile at 20℃; for 0.5 h; Inert atmosphere
Stage #2: at 20℃; Inert atmosphere
General procedure: 2-iodoaniline (500.2 mg, 2.28 mmol, 1.0 equiv) was dissolved in Et3N (4.5 mL). The resulting solution was added with PdCl2(PPh3)2 (32.1 mg, 0.046 mol, 0.02 equiv) and CuI (17.4 mg, 0.091mmol, 0.04 equiv). The orange-yellow solution was degassed by bubbling with a stream of argon into the solution at room temperature for 30 min. After degassing, phenylacetylene (0.30 mL,279.0 mg, 2.73 mmol, 1.2 equiv) was added as a neat liquid into the solution via syringe. The resulting dark brown solution was allowed to stir at room temperature under argon atmosphere overnight. The reaction was quenched by addition of sat. aq. NH4Cl. The separated aqueousphase was extracted with EtOAc (3x times). The combined organic phases were washed with sat. aq. NaCl, dried over anh. Na2SO4, filtered and concentrated to a crude product. The crudeproduct was purified by SiO2 column chromatography eluting with 0-10percent EtOAc-hexane to give 398.2 mg (90percent) of 2-(phenylethynyl)aniline as an orange solid.
75% With sodium hydroxide In toluene at 130℃; for 72 h; General procedure: To a stirred solution of the corresponding 2-iodoaniline (6, 1 mmol) in toluene (3 mL) under argon atmosphere were added Pd/CuO-Fe3O4 (50 mg), NaOH (400 mg, 10 mmol), and the corresponding alkyne (2, 1.5 mmol). The resulting mixture was stirred at 130 °C until the end of reaction (see Table 6). The catalyst was removed by a magnet and the resulting mixture was quenched with water and extracted with EtOAc. The organic phases were dried over MgSO4, followed by evaporation under reduced pressure to remove the solvent. The product was purified by chromatography on silica gel (hexane/ethyl acetate) to give the corresponding compounds 7. Yields are included in Table 6. Then, to a stirred solution of 7 (1 mmol) in toluene (4 mL) was added ZnBr2 (225 mg, 1 mmol). The resulting mixture was stirred at 130 °C during 24 h. The mixture was quenched with water and extracted with EtOAc. The organic phases were dried over MgSO4, followed by evaporation under reduced pressure to give the pure products 8 in quantitative yields. Physical and spectroscopic data for compounds 7 and 8, as well as literature for known compounds, follow.
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[2] Applied Organometallic Chemistry, 2018, vol. 32, # 1,
[3] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 565 - 569
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[6] New Journal of Chemistry, 2018, vol. 42, # 20, p. 16886 - 16890
[7] Tetrahedron Letters, 2018, p. 675 - 680
[8] Liebigs Annalen, 1995, # 5, p. 775 - 780
[9] Applied Organometallic Chemistry, 2014, vol. 28, # 4, p. 298 - 303
[10] Journal of Organic Chemistry, 2010, vol. 75, # 10, p. 3412 - 3419
[11] Tetrahedron, 2012, vol. 68, # 5, p. 1393 - 1400
[12] Synthesis, 2009, # 5, p. 829 - 835
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[14] Tetrahedron Letters, 2004, vol. 45, # 1, p. 35 - 38
[15] Organic Letters, 2008, vol. 10, # 21, p. 4887 - 4889
[16] Journal of Organic Chemistry, 2010, vol. 75, # 21, p. 7502 - 7504
[17] Organic Letters, 2011, vol. 13, # 5, p. 1098 - 1101
[18] Journal of Organic Chemistry, 2012, vol. 77, # 1, p. 617 - 625
[19] Tetrahedron Letters, 2013, vol. 54, # 19, p. 2357 - 2361
[20] Chemistry - A European Journal, 2013, vol. 19, # 25, p. 8294 - 8299
[21] Journal of Organic Chemistry, 2013, vol. 78, # 20, p. 10319 - 10328
[22] Organic Letters, 2013, vol. 15, # 23, p. 5940 - 5943
[23] Chemical Communications, 2014, vol. 50, # 23, p. 3024 - 3026
[24] Chemistry - A European Journal, 2015, vol. 21, # 8, p. 3193 - 3197
[25] Organic Letters, 2015, vol. 17, # 22, p. 5662 - 5665
[26] Journal of Organic Chemistry, 2016, vol. 81, # 10, p. 3994 - 4001
[27] Chemical Communications, 2017, vol. 53, # 1, p. 196 - 199
[28] Advanced Synthesis and Catalysis, 2017, vol. 359, # 8, p. 1373 - 1378
[29] Advanced Synthesis and Catalysis, 2017, vol. 359, # 11, p. 1844 - 1848
[30] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4054 - 4059
[31] Chemical Communications, 2017, vol. 53, # 61, p. 8533 - 8536
[32] Chemical Communications, 2017, vol. 53, # 64, p. 8980 - 8983
[33] Organic Letters, 2017, vol. 19, # 15, p. 3982 - 3985
[34] Organic Letters, 2017, vol. 19, # 22, p. 6128 - 6131
[35] Advanced Synthesis and Catalysis, 2018, vol. 360, # 18, p. 3460 - 3465
[36] Journal of Organic Chemistry, 2017, vol. 82, # 23, p. 12386 - 12394
[37] Journal of Organic Chemistry, 2018, vol. 83, # 17, p. 10453 - 10464
[38] Organic Letters, 2018,
  • 2
  • [ 52670-38-9 ]
  • [ 696-62-8 ]
  • [ 157869-15-3 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 43, p. 14441 - 14448
[2] European Journal of Organic Chemistry, 2010, # 5, p. 818 - 822
[3] Organic Letters, 2013, vol. 15, # 14, p. 3710 - 3713
[4] Organic Letters, 2014, vol. 16, # 14, p. 3720 - 3723
[5] Organic and Biomolecular Chemistry, 2015, vol. 13, # 16, p. 4652 - 4656
  • 3
  • [ 615-36-1 ]
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Reference: [1] Organic Letters, 2009, vol. 11, # 16, p. 3598 - 3601
  • 4
  • [ 615-43-0 ]
  • [ 157869-15-3 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 14, p. 3710 - 3713
[2] Organic Letters, 2014, vol. 16, # 14, p. 3720 - 3723
[3] Organic and Biomolecular Chemistry, 2015, vol. 13, # 16, p. 4652 - 4656
[4] Journal of the American Chemical Society, 2016, vol. 138, # 43, p. 14441 - 14448
  • 5
  • [ 103529-16-4 ]
  • [ 157869-15-3 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 14, p. 3710 - 3713
[2] Organic Letters, 2014, vol. 16, # 14, p. 3720 - 3723
[3] Organic and Biomolecular Chemistry, 2015, vol. 13, # 16, p. 4652 - 4656
[4] Journal of the American Chemical Society, 2016, vol. 138, # 43, p. 14441 - 14448
  • 6
  • [ 52670-38-9 ]
  • [ 623-12-1 ]
  • [ 157869-15-3 ]
Reference: [1] European Journal of Organic Chemistry, 2013, # 26, p. 5864 - 5870
  • 7
  • [ 149457-45-4 ]
  • [ 157869-15-3 ]
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 13, p. 4983 - 4986
  • 8
  • [ 696-62-8 ]
  • [ 157869-15-3 ]
Reference: [1] ChemMedChem, 2016, vol. 11, # 20, p. 2347 - 2360
  • 9
  • [ 3989-14-8 ]
  • [ 157869-15-3 ]
Reference: [1] ChemMedChem, 2016, vol. 11, # 20, p. 2347 - 2360
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