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[ CAS No. 573-20-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 573-20-6
Chemical Structure| 573-20-6
Chemical Structure| 573-20-6
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Product Details of [ 573-20-6 ]

CAS No. :573-20-6 MDL No. :MFCD00021469
Formula : C15H14O4 Boiling Point : -
Linear Structure Formula :- InChI Key :RYWSYCQQUDFMAU-UHFFFAOYSA-N
M.W : 258.27 Pubchem ID :11310
Synonyms :
Acetomenaphthone;Menadiol diacetate;Vitamin K diacetate;NSC 403062;Kapilin
Chemical Name :2-Methylnaphthalene-1,4-diyl diacetate

Calculated chemistry of [ 573-20-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.2
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 71.91
TPSA : 52.6 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.66
Log Po/w (XLOGP3) : 3.04
Log Po/w (WLOGP) : 3.0
Log Po/w (MLOGP) : 2.98
Log Po/w (SILICOS-IT) : 3.28
Consensus Log Po/w : 2.99

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.48
Solubility : 0.0851 mg/ml ; 0.00033 mol/l
Class : Soluble
Log S (Ali) : -3.81
Solubility : 0.04 mg/ml ; 0.000155 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.62
Solubility : 0.00624 mg/ml ; 0.0000242 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.84

Safety of [ 573-20-6 ]

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

Application In Synthesis of [ 573-20-6 ]

* 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 [ 573-20-6 ]
  • Downstream synthetic route of [ 573-20-6 ]

[ 573-20-6 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 58-27-5 ]
  • [ 108-24-7 ]
  • [ 573-20-6 ]
YieldReaction ConditionsOperation in experiment
84.2% With dmap; palladium on activated charcoal; hydrogen In ethyl acetate at 20℃; for 4 h; 2-methyl-l,4-naphthoquinone (1) (20.0 g) was dissolved in ethyl acetate (200 g). Acetic anhydride (29.65 g), DMAP (1.42 g) and Pd/C (0.6 g) were added. The mixture was stirred at room temperature under hydrogen overnight. Pd/ C was filtered out and the filtered liquor was washed with brine. The organic layer was concentrating and recrystallized in water (60 g) and IPA (80 g) solution, thereby obtaining 28.0 g of the title compound as white crystals (yield: 84.2percent, HPLC purity: 99.8percent). The compound was characterized by 'H-NMR: δ 2.27, s, 3H; 2.46, s, 3H; 2.50, s, 3H; 7.27, s, 1H; 7.55-7.62, m, 2H; 7.85-7.89, d, 2H.
84.2% With dmap; palladium on activated charcoal In ethyl acetate at 20℃; Inert atmosphere 2-methyl-l,4-naphthoquinone (1) (20.0 g) was dissolved in ethyl acetate (200 g). Acetic anhydride (29.65 g), DMAP (1.42 g) and Pd/C (0.6 g) were added. The mixture was stirred at room temperature under hydrogen overnight. Pd/ C was filtered out and the filtered liquor was washed with brine. The organic layer was concentrating and recrystallized in water (60 g) and IPA (80 g) solution, thereby obtaining 28.0 g of the title compound as white crystals (yield: 84.2percent, HPLC purity: 99.8percent).
Reference: [1] Patent: WO2016/60670, 2016, A1, . Location in patent: Paragraph 0036-0041
[2] Patent: TW2016/15603, 2016, A, . Location in patent: Paragraph 0049-0051
[3] Journal of Crystallographic and Spectroscopic Research, 1989, vol. 19, # 2, p. 307 - 316
[4] Archiv der Pharmazie, 1973, vol. 306, # 4, p. 257 - 267
  • 2
  • [ 58-27-5 ]
  • [ 64-19-7 ]
  • [ 573-20-6 ]
Reference: [1] Journal of the American Chemical Society, 1939, vol. 61, p. 3216,3220
[2] Gazzetta Chimica Italiana, 1943, vol. 73, p. 225,234
[3] Journal of the American Chemical Society, 1937, vol. 59, p. 662,664
[4] Recueil des Travaux Chimiques des Pays-Bas, 1940, vol. 59, p. 1029,1034
[5] Anales de la Real Sociedad Espanola de Fisica y Quimica, 1929, vol. 27, p. 647,685
[6] Journal of Biological Chemistry, 1933, vol. 103, p. 405,409
[7] Patent: US1984511, 1933, ,
[8] Journal of the American Chemical Society, 1939, vol. 61, p. 3216,3220
[9] Gazzetta Chimica Italiana, 1943, vol. 73, p. 225,234
[10] Journal of the American Chemical Society, 1937, vol. 59, p. 662,664
[11] Recueil des Travaux Chimiques des Pays-Bas, 1940, vol. 59, p. 1029,1034
[12] Anales de la Real Sociedad Espanola de Fisica y Quimica, 1929, vol. 27, p. 647,685
[13] Journal of Biological Chemistry, 1933, vol. 103, p. 405,409
[14] Patent: US1984511, 1933, ,
[15] Patent: US1984511, 1933, ,
[16] Patent: US1984511, 1933, ,
  • 3
  • [ 481-85-6 ]
  • [ 108-24-7 ]
  • [ 573-20-6 ]
Reference: [1] Chemische Berichte, 1921, vol. 54, p. 2917
[2] Advanced Synthesis and Catalysis, 2012, vol. 354, # 7, p. 1301 - 1306
[3] Organic Letters, 2018, vol. 20, # 1, p. 174 - 177
  • 4
  • [ 67-56-1 ]
  • [ 58-27-5 ]
  • [ 108-24-7 ]
  • [ 573-20-6 ]
  • [ 3526-72-5 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 7, p. 1765 - 1771
  • 5
  • [ 58-27-5 ]
  • [ 573-20-6 ]
Reference: [1] Patent: US2357172, 1941, ,
[2] Anales de la Real Sociedad Espanola de Fisica y Quimica, 1929, vol. 27, p. 647,685
[3] Patent: US2334669, 1941, ,
[4] Patent: US2357172, 1941, ,
[5] Anales de la Real Sociedad Espanola de Fisica y Quimica, 1929, vol. 27, p. 647,685
[6] Patent: US2334669, 1941, ,
[7] Chemische Berichte, 1921, vol. 54, p. 2917
  • 6
  • [ 110327-29-2 ]
  • [ 108-24-7 ]
  • [ 573-20-6 ]
Reference: [1] Australian Journal of Chemistry, 1986, vol. 39, p. 2067 - 2074
  • 7
  • [ 17735-17-0 ]
  • [ 573-20-6 ]
Reference: [1] Chemische Berichte, 1921, vol. 54, p. 2917
  • 8
  • [ 861331-93-3 ]
  • [ 573-20-6 ]
Reference: [1] Chemische Berichte, 1921, vol. 54, p. 2917
  • 9
  • [ 481-85-6 ]
  • [ 108-24-7 ]
  • [ 573-20-6 ]
  • [ 110327-29-2 ]
Reference: [1] Takeda Kenkyusho Nenpo, 1951, vol. 10, p. 1,3[2] Chem.Abstr., 1953, p. 3826
  • 10
  • [ 108170-78-1 ]
  • [ 573-20-6 ]
Reference: [1] Journal of the Chemical Society [Section] C: Organic, 1967, p. 949 - 952
  • 11
  • [ 7664-93-9 ]
  • [ 67597-84-6 ]
  • [ 108-24-7 ]
  • [ 573-20-6 ]
Reference: [1] Journal of the Chemical Society, 1950, p. 1737,1738, 1741[2] Journal of the Chemical Society, 1951, p. 1237
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