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[ CAS No. 16382-15-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 16382-15-3
Chemical Structure| 16382-15-3
Chemical Structure| 16382-15-3
Structure of 16382-15-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 16382-15-3 ]

CAS No. :16382-15-3 MDL No. :MFCD00022703
Formula : C12H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :KMVFKXFOPNKHEM-UHFFFAOYSA-N
M.W : 203.24 Pubchem ID :232919
Synonyms :

Calculated chemistry of [ 16382-15-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 59.35
TPSA : 42.09 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) : -5.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.41
Log Po/w (XLOGP3) : 2.97
Log Po/w (WLOGP) : 2.65
Log Po/w (MLOGP) : 1.95
Log Po/w (SILICOS-IT) : 3.19
Consensus Log Po/w : 2.63

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.22
Solubility : 0.123 mg/ml ; 0.000606 mol/l
Class : Soluble
Log S (Ali) : -3.52
Solubility : 0.0618 mg/ml ; 0.000304 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.16
Solubility : 0.0142 mg/ml ; 0.0000697 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.88

Safety of [ 16382-15-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16382-15-3 ]

* 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 [ 16382-15-3 ]
  • Downstream synthetic route of [ 16382-15-3 ]

[ 16382-15-3 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 609-14-3 ]
  • [ 106-49-0 ]
  • [ 16382-15-3 ]
YieldReaction ConditionsOperation in experiment
25%
Stage #1: With hydrogenchloride; sodium nitrite In water at -5℃; for 0.25 h;
Stage #2: With potassium hydroxide; sodium acetate In ethanol; water at 0℃; for 18 h;
Stage #3: With toluene-4-sulfonic acid In toluene at 110℃; for 5 h;
7.2 g (0.104 mol) of sodium nitrite dissolved in 40 ml of water are added, at 5 C., to a mixture of 10.7 g (0.1 mol) of 4-methylaniline, 74 ml of 12 N hydrochloric acid and 140 ml of water. The reaction mixture is stirred for 15 minutes at 5 C. and is neutralized by addition of 8.1 g of sodium acetate. 12.33 g (0.085 mol) of ethyl a-methyl acetoacetate and 80 ml of ethanol are introduced into a three-necked Uask, followed, at 0 C., by 4.8 g (0.085 mol) ofpotassium hydroxide dissolved in 20ml ofwater and 100 g of ice. The diazonium solution prepared above is added dropwise, at 0 C., to this reaction mixture and the resulting mixture is left for 18 hours at 0 C. The aqueous phase is extracted 4 times with 50 ml of ethyl acetate and the organic phases are combined and dried over anhydrous sodium sulphate. The residue is taken up in 100 ml of toluene and 16.3 g (0.085 mol) of para-toluene sulphonic acid monohy drate. The mixture is then heated slowly to 110 C. and maintained at this temperature for S hours. After cooling and then addition of saturated sodium carbonate solution, the insoluble material is removed by ltration and the organic phase is separated out after settling has taken place, dried over anhydrous sodium sulphate and concentrated. The residue is chromatographed on a column of silica gel, eluent:30/70 (v/v) dichloromethane/cyclohexane, to give beige coloured crystals; m.p.=94 C.; yield=25percent.
Reference: [1] Patent: US2004/43995, 2004, A1, . Location in patent: Page 13
  • 2
  • [ 91462-34-9 ]
  • [ 16382-15-3 ]
Reference: [1] Heterocycles, 1984, vol. 22, # 5, p. 1211 - 1216
[2] Justus Liebigs Annalen der Chemie, 1887, vol. 239, p. 227
[3] Gazzetta Chimica Italiana, 1957, vol. 87, p. 949,953, 958
  • 3
  • [ 2999-46-4 ]
  • [ 90221-55-9 ]
  • [ 16382-15-3 ]
Reference: [1] Chemical Communications, 2009, # 48, p. 7581 - 7583
  • 4
  • [ 617-35-6 ]
  • [ 106-49-0 ]
  • [ 16382-15-3 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 23, p. 14472 - 14488
  • 5
  • [ 22121-86-4 ]
  • [ 29289-13-2 ]
  • [ 16382-15-3 ]
Reference: [1] European Journal of Organic Chemistry, 2011, # 34, p. 6902 - 6908
  • 6
  • [ 952016-37-4 ]
  • [ 16382-15-3 ]
Reference: [1] Catalysis Science and Technology, 2015, vol. 5, # 2, p. 697 - 704
  • 7
  • [ 235759-00-9 ]
  • [ 16382-15-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1999, vol. 47, # 6, p. 791 - 797
  • 8
  • [ 16382-10-8 ]
  • [ 16382-15-3 ]
Reference: [1] Tetrahedron, 2016, vol. 72, # 22, p. 3014 - 3021
  • 9
  • [ 64-17-5 ]
  • [ 89314-29-4 ]
  • [ 16382-15-3 ]
Reference: [1] Journal of Biological Chemistry, 1925, vol. 62, p. 507
  • 10
  • [ 5858-28-6 ]
  • [ 16382-15-3 ]
Reference: [1] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 12, p. 4309 - 4315
  • 11
  • [ 66424-92-8 ]
  • [ 16382-15-3 ]
Reference: [1] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 12, p. 4309 - 4315
  • 12
  • [ 89693-79-8 ]
  • [ 16382-15-3 ]
Reference: [1] Tetrahedron, 2016, vol. 72, # 22, p. 3014 - 3021
  • 13
  • [ 637-60-5 ]
  • [ 16382-15-3 ]
Reference: [1] Tetrahedron, 2016, vol. 72, # 22, p. 3014 - 3021
  • 14
  • [ 106-49-0 ]
  • [ 16382-15-3 ]
Reference: [1] Tetrahedron, 2016, vol. 72, # 22, p. 3014 - 3021
  • 15
  • [ 2028-84-4 ]
  • [ 16382-15-3 ]
Reference: [1] Journal of Biological Chemistry, 1925, vol. 62, p. 507
  • 16
  • [ 539-44-6 ]
  • [ 16382-15-3 ]
Reference: [1] Journal of Biological Chemistry, 1925, vol. 62, p. 507
  • 17
  • [ 89-87-2 ]
  • [ 16382-15-3 ]
Reference: [1] Catalysis Science and Technology, 2015, vol. 5, # 2, p. 697 - 704
  • 18
  • [ 108-38-3 ]
  • [ 16382-15-3 ]
Reference: [1] Journal of the Chemical Society, 1949, p. Spl. 231
  • 19
  • [ 89-87-2 ]
  • [ 95-92-1 ]
  • [ 16382-15-3 ]
Reference: [1] Journal of the Chemical Society, 1949, p. Spl. 231
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