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[ CAS No. 3549-23-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 3549-23-3
Chemical Structure| 3549-23-3
Structure of 3549-23-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 3549-23-3 ]

CAS No. :3549-23-3 MDL No. :MFCD00051913
Formula : C13H18O2 Boiling Point : -
Linear Structure Formula :- InChI Key :HXVTYMWVMVKVTF-UHFFFAOYSA-N
M.W : 206.28 Pubchem ID :605629
Synonyms :

Calculated chemistry of [ 3549-23-3 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.46
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 61.58
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.85
Log Po/w (XLOGP3) : 3.5
Log Po/w (WLOGP) : 2.7
Log Po/w (MLOGP) : 3.13
Log Po/w (SILICOS-IT) : 3.32
Consensus Log Po/w : 3.1

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.36
Solubility : 0.0909 mg/ml ; 0.000441 mol/l
Class : Soluble
Log S (Ali) : -3.74
Solubility : 0.0379 mg/ml ; 0.000184 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.09
Solubility : 0.0166 mg/ml ; 0.0000804 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.57

Safety of [ 3549-23-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3549-23-3 ]

* 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 [ 3549-23-3 ]
  • Downstream synthetic route of [ 3549-23-3 ]

[ 3549-23-3 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 39895-55-1 ]
  • [ 3549-23-3 ]
Reference: [1] ACS Catalysis, 2018, vol. 8, # 1, p. 738 - 741
  • 2
  • [ 19692-45-6 ]
  • [ 3549-23-3 ]
Reference: [1] Farmaco, 1999, vol. 54, # 10, p. 684 - 694
  • 3
  • [ 67-56-1 ]
  • [ 3288-99-1 ]
  • [ 3549-23-3 ]
Reference: [1] Farmaco, 1999, vol. 54, # 10, p. 684 - 694
  • 4
  • [ 3549-23-3 ]
  • [ 32857-63-9 ]
YieldReaction ConditionsOperation in experiment
39% With sodium hydroxide In methanol; water at 20℃; Methyl 4-tert-butylphenylacetate (4.13g, 20 mmol) was dissolved in MeOH (160 mL) and treated with water (40 mL) and NaOH(1.2 g, 30 mmol). The reaction was stirred at room temperature overnight. Thevolatiles were removed under reduced pressure and the remaining residue wasdiluted with water and acidified to pH 4 with 1 N sulfuric acid. The resultingsolids were filtered, washed with water and dried to give 4-tert-butylphenylacetic acid 8a as a white solid (39percent). 1H NMR (400 MHz, CDCl3) δH 1.32 (s, 9 H), 3.60 (s,2 H), 7.22 (d, J = 8.2 Hz, 2 H), 7.35(d, J = 8.2 Hz, 2 H), 8.48 (s, 1 H)ppm; 13C NMR (101 MHz, CDCl3) δC 31.49 (3),34.62, 40.84, 125.70 (2), 129.16 (2), 130.57, 150.29, 177.92 ppm.
9.32 g With sodium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 3 h; (1)
To a solution of 4-tert-butylphenyl acetic acid methyl ester (10.0 g, 48.5 mmol) in a mixture of tetrahydrofuran (50 mL) and methanol (50 mL) was added 6 mol/L aqueous sodium hydroxide solution (16.2 mL, 97.0 mmol), and the mixture was stirred at room temperature for 3 hr.
The mixture was concentrated under reduced pressure and 6 mol/L hydrochloric acid was added thereto while cooling in ice, to adjust the pH to 4 to 5.
A precipitated solid was collected by filtration to afford (4-tert-butylphenyl)acetic acid as a colorless powder (9.32 g).
Reference: [1] Tetrahedron Asymmetry, 2016, vol. 27, # 19, p. 936 - 942
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 9, p. 2047 - 2050
[3] Journal of Medicinal Chemistry, 2000, vol. 43, # 23, p. 4354 - 4358
[4] Patent: WO2004/69792, 2004, A2, . Location in patent: Page 125
[5] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 9, p. 2386 - 2391
[6] Patent: EP2687507, 2014, A1, . Location in patent: Paragraph 0283
  • 5
  • [ 3549-23-3 ]
  • [ 32857-63-9 ]
YieldReaction ConditionsOperation in experiment
99% With sulfuric acid In methanol; water EXAMPLE 3
(Method H):
Synthesis of 5-tert-butyl-2-(1H-pyrazol-4-yl)aniline
Methyl 4-t-butylphenylacetate (20 mmol) was dissolved in MeOH (160 mL) and treated with water (40 mL) and LiOH monohydrate (30 mmol).
The reaction was allowed to stir at room temperature overnight.
The volatiles were removed under reduced pressure and the remaining residue was diluted with water and neutralized to pH 4 with 1 N sulfuric acid.
The resulting solids were filtered, washed with water and dried to leave 4-t-butylphenylacetic acid as an off-white solid (3.8 g, 99percent).
Reference: [1] Patent: US6492393, 2002, B1,
  • 6
  • [ 3549-23-3 ]
  • [ 5406-86-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 49, p. 15364 - 15368[2] Angew. Chem., 2016, # 128, p. 15590 - 15594,5
[3] Journal of Organic Chemistry, 2009, vol. 74, # 6, p. 2598 - 2600
[4] Farmaco, 1999, vol. 54, # 10, p. 684 - 694
[5] European Journal of Organic Chemistry, 2013, # 11, p. 2061 - 2065
[6] Journal of Medicinal Chemistry, 2002, vol. 45, # 7, p. 1395 - 1398
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