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[ CAS No. 24188-74-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 24188-74-7
Chemical Structure| 24188-74-7
Chemical Structure| 24188-74-7
Structure of 24188-74-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 24188-74-7 ]

CAS No. :24188-74-7 MDL No. :MFCD08436984
Formula : C9H6ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :YWUCOQGBXQHOJM-UHFFFAOYSA-N
M.W : 179.60 Pubchem ID :10012505
Synonyms :

Calculated chemistry of [ 24188-74-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.78
TPSA : 33.12 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) : -5.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.44
Log Po/w (XLOGP3) : 2.71
Log Po/w (WLOGP) : 2.59
Log Po/w (MLOGP) : 2.16
Log Po/w (SILICOS-IT) : 2.6
Consensus Log Po/w : 2.3

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.28
Solubility : 0.0948 mg/ml ; 0.000528 mol/l
Class : Soluble
Log S (Ali) : -3.06
Solubility : 0.157 mg/ml ; 0.000873 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.74
Solubility : 0.0327 mg/ml ; 0.000182 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.35

Safety of [ 24188-74-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 24188-74-7 ]

* 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 [ 24188-74-7 ]
  • Downstream synthetic route of [ 24188-74-7 ]

[ 24188-74-7 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 1615-02-7 ]
  • [ 26386-88-9 ]
  • [ 24188-74-7 ]
YieldReaction ConditionsOperation in experiment
53%
Stage #1: With triethylamine In benzene for 2 h;
Stage #2: at 90℃; for 3.5 h; Reflux
Step 1To a solution of (is)-3-(4-chlorophenyl)acrylic acid (18.3 g, 0.1 mol) and Et3 (20.2 g, 0.2 mol) in benzene (100 mL) was added dropwise DPPA (27.5 g, 0.1 mol). After stirring for 2 h, the solution was concentrated and purified by chromatography (Biotage, mobile phase 20/80 EtOAc/hexanes) to give 16 g of an intermediate azide as a solid. This intermediate was dissolved in 100 mL of PI12CH2 and the resulting mixture was slowly heated to 90 °C over a 30 min time period. The reaction mixture was heated to reflux and maintained at this temperature for 3h. After cooling to RT, a solid precipitated which was collected by filtration and washed with toluene to provide 9.5 g of 7-chloroisoquinolin-l(2H)-one (53percent). XH NMR (400 MHz, CD3OD) δ ppm 6.66 (d, J=7.05 Hz, 1 H), 7.18 (d, J=7.05 Hz, 1 H), 7.66 (s, 1 H) 7.67 (d, J=2.01 Hz, 1 H), 8.24 (d, J=2.27 Hz, 1 H); 13C NMR (101 MHz, DMSO-D6) δ ppm 104.05, 125.62, 127.21, 128.54, 129.52, 130.77, 132.43, 136.55, 160.72; LC/MS, MS m/z (M+H)+ 180.
Reference: [1] Patent: WO2012/166459, 2012, A1, . Location in patent: Page/Page column 23-24
  • 2
  • [ 1028252-12-1 ]
  • [ 24188-74-7 ]
Reference: [1] Patent: US2010/56792, 2010, A1, . Location in patent: Page/Page column 6
  • 3
  • [ 131002-05-6 ]
  • [ 24188-74-7 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 5, p. 1419 - 1424
  • 4
  • [ 130874-98-5 ]
  • [ 24188-74-7 ]
Reference: [1] Helvetica Chimica Acta, 1990, vol. 73, # 4, p. 763 - 781
  • 5
  • [ 131002-02-3 ]
  • [ 24188-74-7 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 5, p. 1419 - 1424
  • 6
  • [ 83421-78-7 ]
  • [ 24188-74-7 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 29, p. 5761 - 5766
  • 7
  • [ 50712-70-4 ]
  • [ 24188-74-7 ]
Reference: [1] Helvetica Chimica Acta, 1990, vol. 73, # 4, p. 763 - 781
  • 8
  • [ 24188-74-7 ]
  • [ 630420-16-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 5, p. 1730 - 1752
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 5, p. 1730 - 1752
  • 9
  • [ 24188-74-7 ]
  • [ 630420-16-5 ]
Reference: [1] Patent: WO2012/166459, 2012, A1,
  • 10
  • [ 24188-74-7 ]
  • [ 1028252-13-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 5, p. 1730 - 1752
[2] Patent: US2009/274652, 2009, A1, . Location in patent: Page/Page column 36-37
[3] Patent: US2009/285773, 2009, A1, . Location in patent: Page/Page column 15-16
[4] Patent: US2008/119461, 2008, A1, . Location in patent: Page/Page column 62-63
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