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[ CAS No. 35212-22-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 35212-22-7
Chemical Structure| 35212-22-7
Chemical Structure| 35212-22-7
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Product Details of [ 35212-22-7 ]

CAS No. :35212-22-7 MDL No. :MFCD00221719
Formula : C18H16O3 Boiling Point : -
Linear Structure Formula :(C3H7O)C15H9O2 InChI Key :SFBODOKJTYAUCM-UHFFFAOYSA-N
M.W : 280.32 Pubchem ID :3747
Synonyms :
7-Isopropoxyisoflavone;Osteofix;TC 80;Yambolap;FL-113
Chemical Name :7-Isopropoxy-3-phenyl-4H-chromen-4-one

Calculated chemistry of [ 35212-22-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.17
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 84.03
TPSA : 39.44 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.27
Log Po/w (XLOGP3) : 3.95
Log Po/w (WLOGP) : 4.25
Log Po/w (MLOGP) : 2.39
Log Po/w (SILICOS-IT) : 4.59
Consensus Log Po/w : 3.69

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.43
Solubility : 0.0104 mg/ml ; 0.000037 mol/l
Class : Moderately soluble
Log S (Ali) : -4.48
Solubility : 0.00932 mg/ml ; 0.0000332 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.69
Solubility : 0.0000574 mg/ml ; 0.000000205 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.03

Safety of [ 35212-22-7 ]

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 [ 35212-22-7 ]

* 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 [ 35212-22-7 ]
  • Downstream synthetic route of [ 35212-22-7 ]

[ 35212-22-7 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 13057-72-2 ]
  • [ 75-26-3 ]
  • [ 35212-22-7 ]
YieldReaction ConditionsOperation in experiment
42% With potassium carbonate In DMF (N,N-dimethyl-formamide) at 80℃; for 4 h; To a solution of 2.50 g of analog 1 (10.5 mmol) in 30 ml of DMF was added 1.80 g of anhydrous IL2CO3 (13.0 mmol) and 3.0 ml of 2-bromopropane (32.0 mmol). The mixture was stirred at 80 °C for 4 hours and then poured into ice water. Precipitates were collected by filtration, washed with small portions of water, and dried to give a residue of crude product. The residue was loaded onto a Sephadex LH-20 column (chloroform : methanol, 7: 3) and fractions that contained pure product were pooled, concentrated, and recrystallized from acetone to give 1.05 g of crystalline analog 5, a yield of 42 percent (w/w): mp 110-111 °C. 1H NMR (DMSO-d6) 8 1.33 (-CH3), 1.34 (-CH3), 4.86 (m, 1H, >CH2-), 7.05 (dd, 1H, J= 8. 86, 2.20 Hz, 6-H), 7.16 (d, 1H, J= 2. 50 Hz, 8H), 7.38 (t, 1H, J= 6.78 Hz, 4'-H), 7.44 (t, 2H, J= 7.76, 1.6 Hz, 3', 5'-H), 7.59 (d, 2H, J= 8.09, 1.6 Hz, 2', 6'-H), 8. 02 (d, IH, J= 8. 86 Hz, 5-H), 8. 46 (s, 1H, 2-H). 13C NMR (DMSO-d6) 8 21.5 (-CH3), 21.5 (-CH3), 70.4 (-CH2-O-), 101. 8 (C-8), 115.7 (C-6), 117.3 (C-10), 123.7 (C-3), 127.0 (C-1'), 127.8 (C-5), 128.1 (C-3', 5'), 128.9 (C-2', 6'), 132.0 (C4'), 154.0 (C-2), 157.5 (C-9), 162.0 (C-7), 174.1 (C-4). MS (m/z) 281.4 (M + H) +, 303. 3 (M + Na) +, 319.4 (M + K) +, 279.5 (M-H)-. Anal. (C23H2405) for C, H. Cacld : 77.12, 5.75 ; found: 76.50, 5.69.
Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 1999, vol. 42, # 5, p. 497 - 504
[2] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 18, p. 4069 - 4081
[3] Patent: WO2004/2470, 2004, A1, . Location in patent: Page/Page column 22-23
[4] Patent: US3949085, 1976, A,
  • 2
  • [ 13057-72-2 ]
  • [ 75-26-3 ]
  • [ 78-92-2 ]
  • [ 35212-22-7 ]
YieldReaction ConditionsOperation in experiment
96.6% With potassium carbonate In <i>N</i>-methyl-acetamide; ethanol; water EXAMPLE 1D
Preparation of Ipriflavone (I)
7-Hydroxyisoflavone (35 kg), dimethylformamide (35 kg), potassium carbonate (35 kg) and isopropyl bromide (25 kg) were fed to a reactor.
The reaction mass was heated to 70° C. for 6 h and added, at said temperature, with sec-butyl alcohol (90 kg) and water (300 kg).
Then it was cooled.
The solid was filtered and washed with water.
The wet solid was dissolved in ethanol (200 kg) at boiling.
The solution was cooled and the solid precipitate was filtered, washed with ethanol and dried at 70° C.
39.7 kg of 7-isopropoxy-isoflavone was obtained.
Stoichiometric yield =96.6percent.
Chromatographic purity: (HPLC) >=99.9percent.
Reference: [1] Patent: US5973169, 1999, A,
  • 3
  • [ 75-30-9 ]
  • [ 13057-72-2 ]
  • [ 35212-22-7 ]
Reference: [1] Pharmaceutical Chemistry Journal, 1990, vol. 24, # 9, p. 641 - 645[2] Khimiko-Farmatsevticheskii Zhurnal, 1990, vol. 24, # 9, p. 38 - 41
  • 4
  • [ 595-90-4 ]
  • [ 35212-22-7 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 19, p. 9422 - 9427
  • 5
  • [ 1092975-69-3 ]
  • [ 35212-22-7 ]
Reference: [1] Synthetic Communications, 2008, vol. 38, # 22, p. 3875 - 3883
  • 6
  • [ 3669-41-8 ]
  • [ 35212-22-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 18, p. 4069 - 4081
[2] Pharmaceutical Chemistry Journal, 1990, vol. 24, # 9, p. 641 - 645[3] Khimiko-Farmatsevticheskii Zhurnal, 1990, vol. 24, # 9, p. 38 - 41
  • 7
  • [ 38111-44-3 ]
  • [ 35212-22-7 ]
Reference: [1] Journal of Molecular Structure, 2017, vol. 1149, p. 235 - 242
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