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[ CAS No. 2222-33-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 2222-33-5
Chemical Structure| 2222-33-5
Chemical Structure| 2222-33-5
Structure of 2222-33-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 2222-33-5 ]

CAS No. :2222-33-5 MDL No. :MFCD00003588
Formula : C15H10O Boiling Point : -
Linear Structure Formula :- InChI Key :SNVTZAIYUGUKNI-UHFFFAOYSA-N
M.W : 206.24 Pubchem ID :16679
Synonyms :

Calculated chemistry of [ 2222-33-5 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 67.72
TPSA : 17.07 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) : -4.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.31
Log Po/w (XLOGP3) : 4.15
Log Po/w (WLOGP) : 3.35
Log Po/w (MLOGP) : 2.93
Log Po/w (SILICOS-IT) : 4.11
Consensus Log Po/w : 3.37

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.43
Solubility : 0.00772 mg/ml ; 0.0000374 mol/l
Class : Moderately soluble
Log S (Ali) : -4.22
Solubility : 0.0125 mg/ml ; 0.0000608 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.08
Solubility : 0.000172 mg/ml ; 0.000000836 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.5

Safety of [ 2222-33-5 ]

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 [ 2222-33-5 ]

* 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 [ 2222-33-5 ]
  • Downstream synthetic route of [ 2222-33-5 ]

[ 2222-33-5 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 2222-33-5 ]
  • [ 10354-00-4 ]
YieldReaction ConditionsOperation in experiment
98% With sodium hydroxide; sodium tetrahydroborate In methanol; water [0407] 4 ml of water, 0.45 ml of 1 N aqueous sodium hydroxide solution and 20 ml of a suspension of 1.50 g (7.27 mmol) of dibenzosuberenone in methanol were added to 200 mg (5.29 mmol) of sodium borohydride, and they were stirred overnight. Crystals thus precipitated were taken by the filtration, washed with water and dissolved in ethyl acetate. After drying over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure to obtain the title compound. [0408] Yield: 1.48 g (7.11 mmol), 98percent 1H-NMR (CDCl3): 2.41 (1H, d), 5.43 (1H, d), 7.11 (2H, s), 7.25-7.31 (2H, m), 7.36-7.44 (4H, m), 7.66 (2H, d).
98% With sodium borohydrid In diethyl ether; water A.
5H-Dibenzo[a,d]cyclohepten-5-ol.
5H-Dibenzo[a,d]cyclohepten-5-one (10 g) is dissolved in 80 ml of isopropyl alcohol and sodium borohydride (1.8 g) is added at once.
The mixture is stirred at room temperature for two hr. 5 ml of water are added to quench the reaction and the solvent is evaporated.
The residue is taken up in diethyl ether and washed with water, dried over MgSO4 and evaporated. 9.8 g (98percent yield) of 5H-dibenzo-[a,d]-cyclohepten-5-ol is obtained.
98% With sodium borohydrid In diethyl ether; water A.
5H-Dibenzo[a,d]cyclohepten-5-ol.
5H-Dibenzo[a,d]cyclohepten-5-one (10 g) is dissolved in 80 ml of isopropyl alcohol and sodium borohydride (1.8 g) is added at once.
The mixture is stirred at room temperature for two hr. 5 ml of water are added to quench the reaction and the solvent is evaporated.
The residue is taken up in diethyl ether and washed with water, dried over MgSO4 and evaporated. 9.8 g (98percent yield) of 5H-dibenzo[a,d]cyclohepten-5-ol is obtained.
98% With sodium borohydrid In diethyl ether; water A.
5H-Dibenzo[a,d]cyclohepten-5-ol.
5H-Dibenzo[a,d]cyclohepten-5-one (10 g) is dissolved in 80 ml of isopropyl alcohol and sodium borohydride (1.8 g) is added at once.
The mixture is stirred at room temperature for two hr. 5 ml of water are added to quench the reaction and the solvent is evaporated.
The residue is taken up in diethyl ether and washed with water, dried over MgSO4 and evaporated. 9.8 g (98percent yield) of 5H-dibenzo-[a,d]cyclohepten-5-ol is obtained.
98% With sodium hydroxide; sodium tetrahydroborate In methanol; water 4 ml of water, 0.45 ml of 1 N aqueous sodium hydroxide solution and 20 ml of a suspension of 1.50 g (7.27 mmol) of dibenzosuberenone in methanol were added to 200 mg (5.29 mmol) of sodium borohydride, and they were stirred overnight. Crystals thus precipitated were taken by the filtration, washed with water and dissolved in ethyl acetate. After drying over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure to obtain the title compound. Yield: 1.48 g (7.11 mmol), 98 percent1H-NMR (CDCl3): 2.41 (1H, d), 5.43 (1H, d), 7.11 (2H, s), 7.25-7.31 (2H, m), 7.36-7.44 (4H, m), 7.66 (2H, d).
84% With sodium tetrahydroborate In methanol at 20℃; for 1 h; Large scale Dibenzosuberenone (5H-dibenzo[a,d]cyclohepten-5-one) (1) (12.37 g, 60 mmol) would only partly dissolve in MeOH (200 mL) at room temperature, but upon treatment with sodium borohydride (1.70 g,3 equiv.) and manual swirling, the mixture warmed up to give a homogeneous solution within 0.25 h. After 1 h, acetone (4 mL) was added to destroy the excess borohydride. Most of the solvent was then evaporated off under suction and water (100 mL) was then added tothe residue (30 mL). The precipitate so formed was isolated, dried and recrystallised from petroleum ether–CH2Cl2 to yield the alcohol (2): yield 10.5 g (84percent); m.p. 120–122 °C [lit.4 120 °C]; 1H NMR (CDCl3): δ (ppm) 2.62 (brs, OH), 5.38 (s, 5H), 7.11 (s, 10(11)H2), 7.26–7.46(m, ArH6), 7.67 (d, ArH2); 13C NMR (CDCl3): δ (ppm) 74.6 (CHOH),124.8, 126.8, 128.6, 128.7, 130.9, 132.6, 140.6.

Reference: [1] Patent: US2004/167118, 2004, A1, . Location in patent: Page 29-30
[2] Patent: US4910312, 1990, A,
[3] Patent: US4772615, 1988, A,
[4] Patent: EP221572, 1991, B1,
[5] Patent: EP1481673, 2004, A1, . Location in patent: Page/Page column 42-43
[6] Revue Roumaine de Chimie, 2002, vol. 47, # 3-4, p. 239 - 248
[7] Australian Journal of Chemistry, 1994, vol. 47, # 5, p. 837 - 852
[8] Journal of Chemical Research, 2018, vol. 42, # 3, p. 153 - 155
[9] Journal of the American Chemical Society, 1989, vol. 111, # 13, p. 4887 - 4895
[10] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1978, vol. 16, p. 220 - 225
[11] Gazzetta Chimica Italiana, 1957, vol. 87, p. 293,305
[12] Journal of Organic Chemistry, 1967, vol. 32, p. 472 - 473
[13] Tetrahedron, 1986, vol. 42, # 6, p. 1815 - 1822
[14] Journal of Medicinal Chemistry, 1992, vol. 35, # 22, p. 4238 - 4248
[15] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 3, p. 311 - 314
[16] Chimia, 2003, vol. 57, # 4, p. 187 - 190
[17] Journal of Molecular Structure, 2003, vol. 661-662, # 1-3, p. 121 - 139
[18] Revue Roumaine de Chimie, 2010, vol. 55, # 10, p. 711 - 714
  • 2
  • [ 920-39-8 ]
  • [ 2222-33-5 ]
  • [ 10354-00-4 ]
  • [ 123299-71-8 ]
Reference: [1] Chemical Communications, 2010, vol. 46, # 15, p. 2674 - 2676
[2] Journal of Organic Chemistry, 2010, vol. 75, # 15, p. 5008 - 5016
[3] Chemical Communications, 2010, vol. 46, # 15, p. 2674 - 2676
  • 3
  • [ 2222-33-5 ]
  • [ 931-50-0 ]
  • [ 10354-00-4 ]
  • [ 260416-00-0 ]
Reference: [1] Chemical Communications, 2010, vol. 46, # 15, p. 2674 - 2676
[2] Journal of Organic Chemistry, 2010, vol. 75, # 15, p. 5008 - 5016
[3] Chemical Communications, 2010, vol. 46, # 15, p. 2674 - 2676
  • 4
  • [ 18099-45-1 ]
  • [ 2222-33-5 ]
  • [ 10354-00-4 ]
Reference: [1] Patent: US3965181, 1976, A,
  • 5
  • [ 925-90-6 ]
  • [ 2222-33-5 ]
  • [ 10354-00-4 ]
  • [ 1971-54-6 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 15, p. 5008 - 5016
[2] Journal of Organic Chemistry, 2010, vol. 75, # 15, p. 5008 - 5016
  • 6
  • [ 931-51-1 ]
  • [ 2222-33-5 ]
  • [ 10354-00-4 ]
  • [ 260416-00-0 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 15, p. 5008 - 5016
[2] Journal of Organic Chemistry, 2010, vol. 75, # 15, p. 5008 - 5016
  • 7
  • [ 109-54-6 ]
  • [ 2222-33-5 ]
  • [ 18029-54-4 ]
Reference: [1] Journal of Organic Chemistry, 1962, vol. 27, p. 230 - 240
[2] Patent: WO2012/98563, 2012, A2, . Location in patent: Page/Page column 7
  • 8
  • [ 2222-33-5 ]
  • [ 1027338-06-2 ]
Reference: [1] ChemBioChem, 2011, vol. 12, # 12, p. 1912 - 1921
[2] Patent: US2016/159732, 2016, A1,
[3] Patent: US2016/159732, 2016, A1,
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