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[ CAS No. 66-99-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 66-99-9
Chemical Structure| 66-99-9
Chemical Structure| 66-99-9
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Product Details of [ 66-99-9 ]

CAS No. :66-99-9 MDL No. :MFCD00004094
Formula : C11H8O Boiling Point : -
Linear Structure Formula :- InChI Key :PJKVFARRVXDXAD-UHFFFAOYSA-N
M.W :156.18 Pubchem ID :6201
Synonyms :

Calculated chemistry of [ 66-99-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.34
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.76
Log Po/w (XLOGP3) : 2.42
Log Po/w (WLOGP) : 2.65
Log Po/w (MLOGP) : 2.48
Log Po/w (SILICOS-IT) : 3.16
Consensus Log Po/w : 2.49

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.88
Solubility : 0.204 mg/ml ; 0.00131 mol/l
Class : Soluble
Log S (Ali) : -2.42
Solubility : 0.593 mg/ml ; 0.00379 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.01
Solubility : 0.0154 mg/ml ; 0.0000984 mol/l
Class : Moderately soluble

Medicinal Chemistry

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

Safety of [ 66-99-9 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 66-99-9 ]

* 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 [ 66-99-9 ]
  • Downstream synthetic route of [ 66-99-9 ]

[ 66-99-9 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 66-99-9 ]
  • [ 10315-07-8 ]
Reference: [1] Patent: EP520336, 1992, A2,
  • 2
  • [ 141-82-2 ]
  • [ 66-99-9 ]
  • [ 6342-87-6 ]
YieldReaction ConditionsOperation in experiment
4.2 g
Stage #1: at 80℃; for 6 h;
Stage #2: With 5%-palladium/activated carbon; hydrogen In tetrahydrofuran for 10 h;
Stage #3: at 80℃; for 2 h;
[0570] 2-Naphthalaldehyde (47 g) and malonic acid (62.4 g) were dissolved in pyridine (300 mL), piperidine (18 mL) was added dropwise thereto, and a reaction was then carried out at 80° C. for 6 hours. After leaving to cool, the reaction mixture was poured into a 1N HCl aqueous solution (1 L), and the crystals thus precipitated were filtered and then recrystallized from methanol, thus giving an unsaturated carboxylic acid (50 g). [0571] A 5percent palladium/activated carbon catalyst (0.5 g) was added to a suspension of the unsaturated carboxylic acid (10 g) thus obtained in tetrahydrofuran (100 mL), hydrogen was added using a rubber balloon at normal pressure (1 atm), and a reaction was carried out for 10 hours. The reaction mixture was filtered using Celite and then concentrated, and the crystals thus obtained was reslurried using a mixed solvent of hexane/ethyl acetate, thus giving a saturated carboxylic acid (7.7 g). [0572] The saturated carboxylic acid (7.6 g) thus obtained was dissolved in methanesulfonic acid (80 mL), and a reaction was carried out at 80° C. for 2 hours. The reaction mixture was poured into water (500 mL), and the crystals thus precipitated were filtered, washed with water, then reslurried with diisopropyl ether, filtered, and dried, thus giving a ketone compound (4.2 g).
Reference: [1] Patent: US2013/171415, 2013, A1, . Location in patent: Paragraph 0570; 0571; 0572
  • 3
  • [ 66-99-9 ]
  • [ 613-56-9 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 4, p. 912 - 915
[2] Patent: US9636670, 2017, B2,
  • 4
  • [ 4541-70-2 ]
  • [ 66-99-9 ]
  • [ 613-56-9 ]
Reference: [1] Chemical Physics Letters, 1997, vol. 266, # 5-6, p. 601 - 606
  • 5
  • [ 66-99-9 ]
  • [ 74-89-5 ]
  • [ 76532-33-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1981, vol. 24, # 2, p. 140 - 145
  • 6
  • [ 66-99-9 ]
  • [ 76532-33-7 ]
Reference: [1] Pharmaceutical Chemistry Journal, 2006, vol. 40, # 8, p. 452 - 454
[2] Helvetica Chimica Acta, 1952, vol. 35, p. 1348,1351
[3] Organic Letters, 2011, vol. 13, # 4, p. 600 - 603
  • 7
  • [ 141-82-2 ]
  • [ 66-99-9 ]
  • [ 129042-57-5 ]
YieldReaction ConditionsOperation in experiment
80% With ammonium acetate In butan-1-olReflux General procedure: A mixture of appropriate aldehyde 2.40 g (1-15), 2.44 g ofmalonic acid and 3.54 g of ammonium acetate (1:1.1:2.3), in 200mLof the 1-butanol was refluxed for 1.5-2 h until the evolution of CO2ceased. The precipitate formed was filtered and washed withboiling 1-butanol (2 x 50 mL), boiling ethanol (2 x 50 mL) and100mL of water. Precipitates were dried at 80-100 °C for 8-10 h.Purity of product was checked by TLC, and yield obtained about65-80percent in each reaction.
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 252 - 268
[2] Chemistry - A European Journal, 2006, vol. 12, # 7, p. 1855 - 1874
[3] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1952, p. 113,116[4] Chem.Abstr., 1953, p. 2157
[5] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1952, p. 113,116[6] Chem.Abstr., 1953, p. 2157
[7] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1952, p. 113,116[8] Chem.Abstr., 1953, p. 2157
[9] Journal of Medicinal Chemistry, 1996, vol. 39, # 17, p. 3238 - 3240
[10] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 11, p. 1420 - 1432
  • 8
  • [ 4488-22-6 ]
  • [ 66-99-9 ]
  • [ 18741-85-0 ]
  • [ 18531-95-8 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 14, p. 3684 - 3687[2] Angew. Chem., 2014, vol. 126, # 14, p. 3758 - 3761,4
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