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[ CAS No. 79418-41-0 ] {[proInfo.proName]}

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Chemical Structure| 79418-41-0
Chemical Structure| 79418-41-0
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Product Details of [ 79418-41-0 ]

CAS No. :79418-41-0 MDL No. :MFCD19441226
Formula : C9H7NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :RQFHTIQNYJDJAH-UHFFFAOYSA-N
M.W :177.16 Pubchem ID :57345854
Synonyms :

Calculated chemistry of [ 79418-41-0 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 48.91
TPSA : 76.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.15
Log Po/w (XLOGP3) : 1.11
Log Po/w (WLOGP) : 1.09
Log Po/w (MLOGP) : 0.45
Log Po/w (SILICOS-IT) : 1.22
Consensus Log Po/w : 1.0

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.21
Solubility : 1.1 mg/ml ; 0.00621 mol/l
Class : Soluble
Log S (Ali) : -2.31
Solubility : 0.87 mg/ml ; 0.00491 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.67
Solubility : 0.374 mg/ml ; 0.00211 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.61

Safety of [ 79418-41-0 ]

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 [ 79418-41-0 ]

* 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 [ 79418-41-0 ]
  • Downstream synthetic route of [ 79418-41-0 ]

[ 79418-41-0 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 126940-57-6 ]
  • [ 79418-41-0 ]
YieldReaction ConditionsOperation in experiment
87.7%
Stage #1: With hydrogenchloride; water In propan-1-ol for 10 h; Heating / reflux
Stage #2: With sodium hydrogencarbonate In propan-1-ol; water
(1)
Preparation of 3-amino-7-hydroxy-2H-1-benzopyran-2-one.
A mixture of N-(7-hydroxy-2-oxo-2H-1-benzopyran-3-yl)benzamide (230 mg, 0.82 mmol), 1-propanol (6 ml) and concentrated hydrochloric acid (2 ml) was refluxed for 3 hours.
Then, hydrochloric acid (2 ml) was added and the mixture was refluxed for further 7 hours.
After cooling, the reaction mixture was poured into saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate.
The ethyl acetate layer was washed successively with water and saturated brine, and after the layer was dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (eluent: dichloromethane/ethyl acetate=2/1) to give the title compound as a yellow solid (127 mg, 87.7percent).
1H-NMR(DMSO-d6, δ): 5.23(2H, s), 6.65-6.70(3H, m), 7.23(1H, d, J=8.4 Hz), 9.81(1H, s).
Reference: [1] Patent: US2005/54717, 2005, A1, . Location in patent: Page/Page column 7
  • 2
  • [ 1616370-98-9 ]
  • [ 79418-41-0 ]
YieldReaction ConditionsOperation in experiment
98% With 1-methyl-piperazine In water; acetone for 9 h; Reflux General procedure: N-Methylpiperazine(0.29 g, 2.92 mmol, 330 ml, 5 equiv)was added to a suspensionof 1-(2-oxo-7-hydroxy-2H-cromen-3-yl)pyridinium chloride 4f,contaminated with NH4Cl in a 1:0.7 ratio (0.18 g, 0.58 mmol) inacetone (25 ml) and water (0.5 ml). The reaction mixture wasrefluxed for 9 h. The solvent was removed in the rotary evaporatorand flash chromatography was performed using ethyl acetate(30 ml) as eluent. The solvent was removed in the rotary evaporator,resulting in an orange solid, collected and identified as 3-amino-7-hydroxy-2H-chromen-2-one 5f (0.10 g, 0.57 mmol, 98percentyield). Mp 244e245 C; IR (Nujol mull) n 3438, 3347, 3173, 1680, 1609, 1556, 1460 cm1; 1H NMR (300 MHz, DMSO-d6): d 5.22 (s,2H), 6.63e6.69 (m, 3H), 7.22 (d, J8.7 Hz, 1H), 9.80 (s, 1H) ppm; 13CNMR (75 MHz, DMSO-d6): d 101.8, 109.8, 113.0, 113.5, 125.7, 130.2,149.3, 156.1, 159.0 ppm; Anal. Calcd for C9H7NO3: C, 61.02; H, 3.95;N, 7.91. Found: C, 61.31; H, 4.23; N, 8.12.
Reference: [1] Tetrahedron, 2014, vol. 70, # 33, p. 4869 - 4875
  • 3
  • [ 543-24-8 ]
  • [ 95-01-2 ]
  • [ 79418-41-0 ]
Reference: [1] Angewandte Chemie, International Edition, 2009, vol. 48, p. 4034 - 4037[2] Angewandte Chemie, 2009, vol. 121, p. 4094 - 4097
[3] Tetrahedron Letters, 2012, vol. 53, # 39, p. 5280 - 5283
[4] Chemical Communications, 2015, vol. 51, # 11, p. 2029 - 2032
[5] Tetrahedron Letters, 2015, vol. 56, # 42, p. 5761 - 5766
[6] Patent: CN105693674, 2016, A, . Location in patent: Paragraph 0024
[7] Chemical Communications, 2017, vol. 53, # 25, p. 3583 - 3586
  • 4
  • [ 69019-75-6 ]
  • [ 79418-41-0 ]
Reference: [1] Inorganic Chemistry Communications, 2012, vol. 15, p. 12 - 15
[2] Tetrahedron Letters, 2007, vol. 48, # 29, p. 5077 - 5080
[3] Chemistry - A European Journal, 2011, vol. 17, # 12, p. 3326 - 3331
[4] Organic and Biomolecular Chemistry, 2012, vol. 10, # 22, p. 4330 - 4336
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 2779 - 2790
[6] Journal of the American Chemical Society, 2014, vol. 136, # 20, p. 7205 - 7208
[7] Medicinal Chemistry Research, 2014, vol. 23, # 8, p. 3632 - 3643
[8] Tetrahedron, 2016, vol. 72, # 32, p. 4925 - 4930
  • 5
  • [ 79418-42-1 ]
  • [ 79418-41-0 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2011, vol. 46, # 12, p. 1514 - 1519
[2] Journal of Organic Chemistry, 2011, vol. 76, # 12, p. 4964 - 4972
[3] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2012, vol. 90, p. 40 - 44
[4] Bulletin of the Korean Chemical Society, 2014, vol. 35, # 8, p. 2400 - 2402
[5] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 24, p. 5737 - 5742
[6] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 22, p. 5557 - 5561
  • 6
  • [ 946833-00-7 ]
  • [ 79418-41-0 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 29, p. 5077 - 5080
  • 7
  • [ 1573010-11-3 ]
  • [ 79418-41-0 ]
Reference: [1] Medicinal Chemistry Research, 2014, vol. 23, # 8, p. 3632 - 3643
  • 8
  • [ 95-01-2 ]
  • [ 79418-41-0 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 29, p. 5077 - 5080
[2] Journal of Organic Chemistry, 2011, vol. 76, # 12, p. 4964 - 4972
[3] Chemistry of Heterocyclic Compounds, 2011, vol. 46, # 12, p. 1514 - 1519
[4] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2012, vol. 90, p. 40 - 44
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 2779 - 2790
[6] Journal of the American Chemical Society, 2014, vol. 136, # 20, p. 7205 - 7208
[7] Medicinal Chemistry Research, 2014, vol. 23, # 8, p. 3632 - 3643
[8] Bulletin of the Korean Chemical Society, 2014, vol. 35, # 8, p. 2400 - 2402
[9] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 24, p. 5737 - 5742
[10] Tetrahedron, 2016, vol. 72, # 32, p. 4925 - 4930
[11] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 22, p. 5557 - 5561
  • 9
  • [ 33259-31-3 ]
  • [ 79418-41-0 ]
Reference: [1] Journal of Pharmacy and Pharmacology, 2012, vol. 64, # 5, p. 742 - 746
  • 10
  • [ 108-46-3 ]
  • [ 79418-41-0 ]
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 39, p. 5280 - 5283
[2] Tetrahedron Letters, 2015, vol. 56, # 42, p. 5761 - 5766
  • 11
  • [ 673-22-3 ]
  • [ 79418-41-0 ]
Reference: [1] Journal of Pharmacy and Pharmacology, 2012, vol. 64, # 5, p. 742 - 746
  • 12
  • [ 88184-84-3 ]
  • [ 79418-41-0 ]
Reference: [1] Journal of Pharmacy and Pharmacology, 2012, vol. 64, # 5, p. 742 - 746
  • 13
  • [ 1616370-92-3 ]
  • [ 79418-41-0 ]
Reference: [1] Tetrahedron, 2014, vol. 70, # 33, p. 4869 - 4875
  • 14
  • [ 1573010-09-9 ]
  • [ 79418-41-0 ]
Reference: [1] Medicinal Chemistry Research, 2014, vol. 23, # 8, p. 3632 - 3643
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