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[ CAS No. 522-17-8 ] {[proInfo.proName]}

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Chemical Structure| 522-17-8
Chemical Structure| 522-17-8
Structure of 522-17-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 522-17-8 ]

CAS No. :522-17-8 MDL No. :MFCD01740600
Formula : C23H22O6 Boiling Point : -
Linear Structure Formula :- InChI Key :ORDAZKGHSNRHTD-UXHICEINSA-N
M.W : 394.42 Pubchem ID :107935
Synonyms :
(-)-Deguelin;(-)-cis-Deguelin;(−)-cis-Deguelin

Calculated chemistry of [ 522-17-8 ]

Physicochemical Properties

Num. heavy atoms : 29
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.35
Num. rotatable bonds : 2
Num. H-bond acceptors : 6.0
Num. H-bond donors : 0.0
Molar Refractivity : 106.98
TPSA : 63.22 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.86
Log Po/w (XLOGP3) : 3.72
Log Po/w (WLOGP) : 3.9
Log Po/w (MLOGP) : 1.93
Log Po/w (SILICOS-IT) : 4.11
Consensus Log Po/w : 3.5

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.8
Solubility : 0.00621 mg/ml ; 0.0000157 mol/l
Class : Moderately soluble
Log S (Ali) : -4.74
Solubility : 0.00719 mg/ml ; 0.0000182 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.97
Solubility : 0.00042 mg/ml ; 0.00000106 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.67

Safety of [ 522-17-8 ]

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 [ 522-17-8 ]

* 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 [ 522-17-8 ]
  • Downstream synthetic route of [ 522-17-8 ]

[ 522-17-8 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 70191-71-8 ]
  • [ 522-17-8 ]
YieldReaction ConditionsOperation in experiment
61%
Stage #1: With Phenylselenyl chloride In dichloromethane at -30 - 20℃; for 3.16667 h; Inert atmosphere
Stage #2: With dihydrogen peroxide In tetrahydrofuran; water at 0℃;
Comparative Example 1:
Preparation of (7aS,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one (Deguelin)
Phenylselenyl chloride (68 mg, 0.35 mmol) was added to anhydrous CH2Cl2 solution (4.0 mL) containing the compound 8 (128 mg, 0.32 mmol) prepared in Example 1 at -30°C under argon atmosphere, followed by stirring for 10 minutes with maintaining the temperature at -30°C.
The temperature was raised to room temperature with stirring for 2 hours, and then additional stirring was performed for 1 more hour.
The solvent was eliminated from the reaction mixture under reduced pressure and the obtained residue was dissolved in THF (4.0 mL), to which hydrogen peroxide (30percent in water, 0.06 mL) was added 0°C.
The reaction mixture was stirred until the temperature of the mixture reached to room temperature, during which the reaction was monitored with TLC. EtOAc (8.0 mL) and water (4.0 mL) were added thereto.
The organic layer was separated, washed with 5percent NaHCO3 aqueous solution and brine, dried over MgSO4, filtered, and then concentrated.
The obtained non-purified residue was purified by flash column chromatography (EtOAc:n-hexane=1:2) to give deguelin as a light-yellow solid (yield: 61percent, 78 mg).
1H-NMR (CDCl3, 400 MHz) δ 7.72 (d, 1H, J = 8.7 Hz), 6.77 (s, 1H), 6.62 (d, 1H, J = 10.0 Hz), 6.43 (s, 1H), 6.43 (d, 1H, J = 8.7 Hz), 5.53 (d, 1H, J = 10.0 Hz), 4.89 (m, 1H), 4.61 (dd, 1H, J = 12.0, 3.1 Hz), 4.17 (d, 1H, J = 12.0 Hz), 3.82 (d, 1H, J = 4.1 Hz), 3.78 (s, 3H), 3.75 (s, 3H), 1.43 (s, 3H), 1.36 (s, 3 H) ;
13C-NMR (CDCl3, 100 MHz) δ 189.2, 160.0, 156.9, 149.4, 147.4, 143.8, 128.6, 128.5, 115.7, 112.7, 111.4, 110.4, 109.1, 104.7, 100.9, 77.6, 72.4, 66.2, 56.3, 55.8, 44.3, 28.4, 28.1;
HRMS (FAB) Calcd for C23H23O6 (M+H+) : 395.1495, Found: 395.1495.
61%
Stage #1: With Phenylselenyl chloride In dichloromethane at -30 - 20℃; for 3 h; Inert atmosphere
Stage #2: With dihydrogen peroxide In tetrahydrofuran at 0 - 20℃;
Phenylselenyl chloride (68 mg, 0.35 mmol) was added to anhydrous CH2Cl2 solution (4.0 mL) containing the compound 8 (128 mg, 0.32 mmol) prepared in Example 1 at −30° C. under argon atmosphere, followed by stirring for 10 minutes with maintaining the temperature at −30° C. The temperature was raised to room temperature with stirring for 2 hours, and then additional stirring was performed for 1 more hour. The solvent was eliminated from the reaction mixture under reduced pressure and the obtained residue was dissolved in THF (4.0 mL), to which hydrogen peroxide (30percent in water, 0.06 mL) was added 0° C. The reaction mixture was stirred until the temperature of the mixture reached to room temperature, during which the reaction was monitored with TLC. EtOAc (8.0 mL) and water (4.0 mL) were added thereto. The organic layer was separated, washed with 5percent NaHCO3 aqueous solution and brine, dried over MgSO4, filtered, and then concentrated. The obtained non-purified residue was purified by flash column chromatography (EtOAc:n-hexane=1:2) to give deguelin as a light-yellow solid (yield: 61percent, 78 mg). [0584] 1H-NMR (CDCl3, 400 MHz) δ 7.72 (d, 1H, J=8.7 Hz), 6.77 (s, 1H), 6.62 (d, 1H, J=10.0 Hz), 6.43 (s, 1H), 6.43 (d, 1H, J=8.7 Hz), 5.53 (d, 1H, J=10.0 Hz), 4.89 (m, 1H), 4.61 (dd, 1H, J=12.0, 3.1 Hz), 4.17 (d, 1H, J=12.0 Hz), 3.82 (d, 1H, J=4.1 Hz), 3.78 (s, 3H), 3.75 (s, 3H), 1.43 (s, 3H), 1.36 (s, 3H); [0585] 13C-NMR (CDCl3, 100 MHz) δ 189.2, 160.0, 156.9, 149.4, 147.4, 143.8, 128.6, 128.5, 115.7, 112.7, 111.4, 110.4, 109.1, 104.7, 100.9, 77.6, 72.4, 66.2, 56.3, 55.8, 44.3, 28.4, 28.1; [0586] HRMS (FAB) Calcd for C23H23O6 (M+H+): 395.1495. Found: 395.1495.
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 24, p. 10863 - 10884
[2] Patent: EP2871187, 2015, A1, . Location in patent: Paragraph 0482-0486
[3] Patent: US2015/183797, 2015, A1, . Location in patent: Paragraph 0582-0586
[4] Journal of the Chemical Society, Chemical Communications, 1986, # 4, p. 352 - 353
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 13, p. 1685 - 1698
[6] Patent: US2005/191238, 2005, A1, . Location in patent: Page/Page column 34; 35
[7] Organic and Biomolecular Chemistry, 2017, vol. 15, # 7, p. 1593 - 1596
  • 2
  • [ 70145-45-8 ]
  • [ 522-17-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 13, p. 1685 - 1698
  • 3
  • [ 83-79-4 ]
  • [ 522-17-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 24, p. 10863 - 10884
[2] Patent: EP2871187, 2015, A1,
[3] Patent: US2015/183797, 2015, A1,
[4] Organic and Biomolecular Chemistry, 2017, vol. 15, # 7, p. 1593 - 1596
  • 4
  • [ 76-80-2 ]
  • [ 522-17-8 ]
Reference: [1] Chemistry - A European Journal, 2010, vol. 16, # 32, p. 9767 - 9771
  • 5
  • [ 145455-05-6 ]
  • [ 522-17-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 13, p. 1685 - 1698
  • 6
  • [ 70191-70-7 ]
  • [ 522-17-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 24, p. 10863 - 10884
[2] Patent: EP2871187, 2015, A1,
[3] Patent: US2015/183797, 2015, A1,
  • 7
  • [ 58277-58-0 ]
  • [ 522-17-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 7, p. 1593 - 1596
  • 8
  • [ 139006-28-3 ]
  • [ 522-17-8 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1993, vol. 41, # 1, p. 187 - 190
  • 9
  • [ 124571-94-4 ]
  • [ 522-17-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 13, p. 1685 - 1698
  • 10
  • [ 124571-93-3 ]
  • [ 522-17-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 13, p. 1685 - 1698
  • 11
  • [ 2033-89-8 ]
  • [ 522-17-8 ]
  • [ 110508-99-1 ]
Reference: [1] Chemical Communications, 2015, vol. 51, # 43, p. 9026 - 9029
[2] Chemical Communications, 2015, vol. 51, # 43, p. 9026 - 9029
  • 12
  • [ 139006-28-3 ]
  • [ 522-17-8 ]
  • [ 3466-23-7 ]
  • [ 147807-70-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1993, vol. 41, # 1, p. 187 - 190
  • 13
  • [ 186581-53-3 ]
  • [ 147807-70-3 ]
  • [ 522-17-8 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1993, vol. 41, # 1, p. 187 - 190
  • 14
  • [ 73630-64-5 ]
  • [ 123853-56-5 ]
  • [ 522-17-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 13, p. 1685 - 1698
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