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[ CAS No. 17496-14-9 ] {[proInfo.proName]}

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Chemical Structure| 17496-14-9
Chemical Structure| 17496-14-9
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Product Details of [ 17496-14-9 ]

CAS No. :17496-14-9 MDL No. :MFCD00192303
Formula : C10H10O Boiling Point : -
Linear Structure Formula :- InChI Key :BEKNOGMQVKBMQN-UHFFFAOYSA-N
M.W : 146.19 Pubchem ID :249262
Synonyms :

Calculated chemistry of [ 17496-14-9 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.3
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) : -5.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.93
Log Po/w (XLOGP3) : 2.24
Log Po/w (WLOGP) : 2.06
Log Po/w (MLOGP) : 2.01
Log Po/w (SILICOS-IT) : 2.83
Consensus Log Po/w : 2.22

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.56
Solubility : 0.402 mg/ml ; 0.00275 mol/l
Class : Soluble
Log S (Ali) : -2.23
Solubility : 0.853 mg/ml ; 0.00583 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.25
Solubility : 0.0822 mg/ml ; 0.000562 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.89

Safety of [ 17496-14-9 ]

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 [ 17496-14-9 ]

* 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 [ 17496-14-9 ]
  • Downstream synthetic route of [ 17496-14-9 ]

[ 17496-14-9 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 17496-14-9 ]
  • [ 2177-47-1 ]
YieldReaction ConditionsOperation in experiment
82% With sodium tetrahydroborate In toluene EXAMPLE G
2-Methylindene (6)
Analogously to Example D, 5.0 g (34 mmol) of 2-methyl-1-indanone (5) were reduced with 1.94 g (51 mmol) of NaBH4.
The alcohol, which was not purified further, was then further reacted in the presence of 0.2 g of p-toluene-sulfonic acid in 100 ml of toluene at 80° C.
Chromatography on 100 g of silica gel (hexane/methylene chloride 9:1) gave 3.68 g (82percent) of 2-methylindene (6).
1 H-NMR spectrum (100 MHz, CDCl3): 7.2 (4,m), 6.45 (1,m), 3.25 (2,m), 2.1 (3,m).
Mass spectrum: 130 M+, correct disintegration pattern.
Reference: [1] Journal of Chemical Research, 2010, # 6, p. 325 - 329
[2] Journal of Organic Chemistry, 1980, vol. 45, # 23, p. 4564 - 4572
[3] Journal of Organic Chemistry, 1984, vol. 49, # 22, p. 4226 - 4237
[4] Journal of Organic Chemistry, 1982, vol. 47, # 6, p. 1051 - 1058
[5] Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 1, p. 60 - 70
[6] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1974, vol. 28, p. 969 - 980
[7] Patent: US2002/77507, 2002, A1,
[8] Patent: US5840948, 1998, A,
  • 2
  • [ 17496-14-9 ]
  • [ 33223-84-6 ]
  • [ 7732-18-5 ]
  • [ 2177-47-1 ]
YieldReaction ConditionsOperation in experiment
48% With MeMgBr; toluene-4-sulfonic acid; hydroquinone In toluene Part 1
2-methylindene
To an ether solution of MeMgBr (260 ml, 3M) diluted with ether (300 ml) and cooled to 03 C., 2-methylindanone (99.16 g) was added dropwise as an ether solution over 2.5 hours.
After stirring 2.0 hours, the reaction mixture was hydrolyzed with aqueous HCl.
The water phase was separated and extracted twice with ether (300 ml).
The combined organic phases were dried over sodium sulfate.
Evaporation of the solvent gave a crude brown product (107 g) which was distilled under reduced pressure to give 2-methyl-2-indanol (66.2 g) as a white crystalline solid.
2-Methyl-2-indanol (66.2 g) was dissolved in toluene (500 ml) in a 1 liter flask equipped with a Dean-Stark trap.
To this solution p-toluene sulfonic acid (2 g) and a small amount of hydroquinone were added, and the mixture was refluxed for 2.5 hours.
After 8 ml of H2 O was generated, the reaction mixture was cooled to 0° C. and H2 O (1 liter), also cooled to 03 C., was added.
The organic phase was separated and washed three times with water (500 ml).
The toluene was evaporated and the residue (with trace of hydroquinone added) was distilled at reduced pressure to give 2-methylindene (47.2 g, 48percent) as clear slightly green liquid.
Reference: [1] Patent: US5541350, 1996, A,
  • 3
  • [ 147437-87-4 ]
  • [ 29727-02-4 ]
  • [ 2177-47-1 ]
  • [ 17496-14-9 ]
Reference: [1] Journal of the American Chemical Society, 2003, vol. 125, # 11, p. 3248 - 3259
  • 4
  • [ 17496-14-9 ]
  • [ 91817-66-2 ]
Reference: [1] Patent: US2011/124559, 2011, A1,
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