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[ CAS No. 69047-36-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 69047-36-5
Chemical Structure| 69047-36-5
Chemical Structure| 69047-36-5
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Product Details of [ 69047-36-5 ]

CAS No. :69047-36-5 MDL No. :MFCD11109329
Formula : C10H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :JOBIAZYEJOMXEP-UHFFFAOYSA-N
M.W : 159.19 Pubchem ID :11040979
Synonyms :

Calculated chemistry of [ 69047-36-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.1
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.59
TPSA : 22.0 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) : -6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.74
Log Po/w (XLOGP3) : 1.46
Log Po/w (WLOGP) : 1.99
Log Po/w (MLOGP) : 1.18
Log Po/w (SILICOS-IT) : 2.09
Consensus Log Po/w : 1.69

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.24
Solubility : 0.925 mg/ml ; 0.00581 mol/l
Class : Soluble
Log S (Ali) : -1.53
Solubility : 4.72 mg/ml ; 0.0296 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.78
Solubility : 0.264 mg/ml ; 0.00166 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.05

Safety of [ 69047-36-5 ]

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 [ 69047-36-5 ]

* 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 [ 69047-36-5 ]
  • Downstream synthetic route of [ 69047-36-5 ]

[ 69047-36-5 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 1074-88-0 ]
  • [ 74-88-4 ]
  • [ 69047-36-5 ]
YieldReaction ConditionsOperation in experiment
91%
Stage #1: With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide for 0.333333 h; Inert atmosphere
Stage #2: at 20℃; for 12 h;
EXAMPLE I
1-methyl-1H-indole-7-carbaldehyde
20 g 1H-indole-7-carbaldehyde are dissolved in 160 ml N,N-dimethylformamide and combined batchwise with 15.5 g potassium-tert.-butoxide under argon.
After the addition has ended the mixture is left for 20 minutes with stirring and then 8.7 ml methyl iodide are added dropwise.
Then the mixture is left for 12 hours at ambient temperature with stirring and then distributed between water and ethyl acetate.
The aqueous phase is twice extracted with ethyl acetate and the combined organic phases are washed with saturated aqueous sodium chloride solution.
After drying with magnesium sulphate the solvents are eliminated in vacuo.
The residue is extracted from water.
The solid thus obtained is suction filtered and dried in vacuo.
Yield: 20 g (91percent of theory)
Mass spectrum (ESI+): m/z=160 [M+H]+
84%
Stage #1: With caesium carbonate In acetonitrile at 60℃; for 2 h;
Stage #2: at 60℃; for 1 h;
General procedure: To a solution of indole-aldehyde (435mg 3mmol) in CH3CN (30mL) was added Cs2CO3 (829mg, 6mmol), and the mixture was refluxed for 2h. To this solution, alkyl halide (3.3mmol) was added, and the mixture was heated under reflux for 1h. After the completion of the reaction, the solvent was evaporated under reduced pressure and water was added to the reaction mixture and extracted 3 times for ethyl acetate. The combined organic layers were dried over Na2SO4 and concentrated under vacuum. The residue was purified by flash chromatography.
Reference: [1] Patent: US2011/269737, 2011, A1, . Location in patent: Page/Page column 40
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 7, p. 2060 - 2079
[3] Patent: WO2004/52890, 2004, A1, . Location in patent: Page 92-93
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4533 - 4539
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 12, p. 5115 - 5129
  • 2
  • [ 1074-88-0 ]
  • [ 77-78-1 ]
  • [ 69047-36-5 ]
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 14, p. 2903 - 2905
[2] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 14, p. 2261 - 2267
[3] Patent: WO2009/143058, 2009, A1, . Location in patent: Page/Page column 64
  • 3
  • [ 69047-35-4 ]
  • [ 69047-36-5 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995, vol. 34, # 4, p. 285 - 288
  • 4
  • [ 577-19-5 ]
  • [ 69047-36-5 ]
Reference: [1] Journal of Organometallic Chemistry, 2011, vol. 696, # 5, p. 1072 - 1083
  • 5
  • [ 53951-34-1 ]
  • [ 69047-36-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4533 - 4539
  • 6
  • [ 552-89-6 ]
  • [ 69047-36-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4533 - 4539
  • 7
  • [ 51417-51-7 ]
  • [ 69047-36-5 ]
Reference: [1] Journal of Organometallic Chemistry, 2011, vol. 696, # 5, p. 1072 - 1083
  • 8
  • [ 68-12-2 ]
  • [ 280752-68-3 ]
  • [ 69047-36-5 ]
Reference: [1] Journal of Organometallic Chemistry, 2011, vol. 696, # 5, p. 1072 - 1083
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