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[ CAS No. 90401-84-6 ] {[proInfo.proName]}

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Chemical Structure| 90401-84-6
Chemical Structure| 90401-84-6
Structure of 90401-84-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 90401-84-6 ]

CAS No. :90401-84-6 MDL No. :MFCD02179289
Formula : C11H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :FGWRKZJKRYCDOF-UHFFFAOYSA-N
M.W : 171.20 Pubchem ID :10899132
Synonyms :

Calculated chemistry of [ 90401-84-6 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.27
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.01
TPSA : 40.86 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) : -6.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.81
Log Po/w (XLOGP3) : 1.74
Log Po/w (WLOGP) : 2.08
Log Po/w (MLOGP) : 1.29
Log Po/w (SILICOS-IT) : 2.97
Consensus Log Po/w : 1.98

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.34
Solubility : 0.784 mg/ml ; 0.00458 mol/l
Class : Soluble
Log S (Ali) : -2.21
Solubility : 1.04 mg/ml ; 0.0061 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.48
Solubility : 0.0572 mg/ml ; 0.000334 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.77

Safety of [ 90401-84-6 ]

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 [ 90401-84-6 ]

* 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 [ 90401-84-6 ]
  • Downstream synthetic route of [ 90401-84-6 ]

[ 90401-84-6 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 90401-84-6 ]
  • [ 3470-46-0 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1984, vol. 32, # 1, p. 130 - 151
[2] Journal of Organic Chemistry, 1962, vol. 27, p. 70 - 76
[3] Patent: US7115750, 2006, B1, . Location in patent: Page/Page column 163-164
  • 2
  • [ 557-21-1 ]
  • [ 144464-64-2 ]
  • [ 90401-84-6 ]
YieldReaction ConditionsOperation in experiment
41% at 135℃; Step 2:
5-Oxo-5,6,7,8-tetrahydro-naphthalene-2-carbonitrile
A mixture of 5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (11.5 g, 39.0 mmol), prepared in the previous step, and zinc cyanide (2.7 g, 23.5 mmol) in dry dimethylformamide (100 mL) was degassed and put under a nitrogen atmosphere. Tetrakis(triphenylphosphine)palladium(0) (1.7 g, 1.5 mmol) was added and the mixture again degassed and put under a nitrogen atmosphere.
The mixture was stirred at 135° C. overnight.
An additional 171 mg of tetrakis(triphenylphosphine)palladium(0) was added and the reaction stirred for another 4 h.
The reaction mixture was filtered through the Celite.(TM). reagent and rinsed with ethyl acetate.
The filtrate was washed with water.
The layers were separated and the organic layer was dried over anhydrous sodium sulfate.
The organic layer was filtered and concentrated in vacuo to give 8.1 g of crude product.
Purification of the crude product on silica gel using a step-wise gradient of 5percent to 15percent ethyl acetate: hexane as the eluent gave 5-oxo-5,6,7,8-tetrahydro-naphthalene-2-carbonitrile (2.8 g, 41percent), MS(ES) m/z 172 [M+H]+.
41% at 135℃; Step 2:
5-Oxo-5,6,7,8-tetrahydro-naphthalene-2-carbonitrile
A mixture of 5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (11.5 g, 39.0 mmol), prepared in the previous step, and zinc cyanide (2.7 g, 23.5 mmol) in dry dimethylformamide (100 mL) was degassed and put under a nitrogen atmosphere. Tetrakis(triphenylphosphine)palladium(0) (1.7 g, 1.5 mmol) was added and the mixture again degassed and put under a nitrogen atmosphere.
The mixture was stirred at 135° C. overnight.
An additional 171 mg of tetrakis(triphenylphosphine)palladium(0) was added and the reaction stirred for another 4 h.
The reaction mixture was filtered through the Celite.(TM). reagent and rinsed with ethyl acetate.
The filtrate was washed with water.
The layers were separated and the organic layer was dried over anhydrous sodium sulfate.
The organic layer was filtered and concentrated in vacuo to give 8.1 g of crude product.
Purification of the crude product on silica gel using a step-wise gradient of 5percent to 15percent ethyl acetate:hexane as the eluent gave 5-oxo-5,6,7,8-tetrahydro-naphthalene-2-carbonitrile (2.8 g, 41percent), MS (ES) m/z 172 [M+H]+.
Reference: [1] Patent: US2008/45578, 2008, A1, . Location in patent: Page/Page column 18
[2] Patent: US2008/45556, 2008, A1, . Location in patent: Page/Page column 41-42
  • 3
  • [ 151-50-8 ]
  • [ 144464-64-2 ]
  • [ 90401-84-6 ]
Reference: [1] Synthetic Communications, 1993, vol. 23, # 21, p. 2965 - 2971
  • 4
  • [ 3470-53-9 ]
  • [ 151-50-8 ]
  • [ 90401-84-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1984, vol. 32, # 1, p. 130 - 151
  • 5
  • [ 3470-50-6 ]
  • [ 90401-84-6 ]
Reference: [1] Synthetic Communications, 1993, vol. 23, # 21, p. 2965 - 2971
[2] Patent: US2008/45578, 2008, A1,
[3] Patent: US2008/45556, 2008, A1,
  • 6
  • [ 1078-19-9 ]
  • [ 90401-84-6 ]
Reference: [1] Synthetic Communications, 1993, vol. 23, # 21, p. 2965 - 2971
  • 7
  • [ 50878-03-0 ]
  • [ 90401-84-6 ]
Reference: [1] Journal of Organic Chemistry, 1962, vol. 27, p. 70 - 76
  • 8
  • [ 3470-53-9 ]
  • [ 544-92-3 ]
  • [ 90401-84-6 ]
Reference: [1] Journal of Organic Chemistry, 1962, vol. 27, p. 70 - 76
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