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[ CAS No. 1615-02-7 ] {[proInfo.proName]}

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Chemical Structure| 1615-02-7
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Product Details of [ 1615-02-7 ]

CAS No. :1615-02-7 MDL No. :MFCD00004396
Formula : C9H7ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :GXLIFJYFGMHYDY-ZZXKWVIFSA-N
M.W : 182.60 Pubchem ID :637797
Synonyms :

Calculated chemistry of [ 1615-02-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.12
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.81
Log Po/w (XLOGP3) : 2.44
Log Po/w (WLOGP) : 2.33
Log Po/w (MLOGP) : 2.47
Log Po/w (SILICOS-IT) : 2.34
Consensus Log Po/w : 2.28

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.75
Solubility : 0.327 mg/ml ; 0.00179 mol/l
Class : Soluble
Log S (Ali) : -2.87
Solubility : 0.248 mg/ml ; 0.00136 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.48
Solubility : 0.609 mg/ml ; 0.00333 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.78

Safety of [ 1615-02-7 ]

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 [ 1615-02-7 ]

* 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 [ 1615-02-7 ]
  • Downstream synthetic route of [ 1615-02-7 ]

[ 1615-02-7 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 1615-02-7 ]
  • [ 6282-88-8 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran for 12 h; Inert atmosphere; Cooling with ice; Reflux
Stage #2: With hydrogenchloride; water In tetrahydrofuran at 0 - 20℃; for 0.5 h;
9.1 3-(4-Chloro-phenyl)-propan-1-olTo a suspension of lithium aluminium hydride (20.26 g, 37.95 mmol) in THF (tetrahy- drofuran) (300 mL) under nitrogen atmosphere was slowly added a solution of 3-(4- chloro-phenyl)-acrylic acid (65.00 g, 355.96 mmol) in THF (500 mL) under cooling with an ice bath. The resulting mixture was stirred until it reached room temperature and then refluxed for 12 h. After cooling to room temperature, a 10percent HCI solution was added at 0° C and the resultant solution was stirred for 0.5 h. The mixture was then extracted with MTBE (methyl tert-butyl ether) and the organic layers were washed with water, dried and evaporated. The title compound was obtained as a brown oil (70.0 g, 98percent).
Reference: [1] Patent: WO2010/146111, 2010, A1, . Location in patent: Page/Page column 113-114
[2] Organic Letters, 2012, vol. 14, # 17, p. 4394 - 4397
[3] Tetrahedron Letters, 2015, vol. 56, # 8, p. 1045 - 1048
  • 2
  • [ 1615-02-7 ]
  • [ 6282-88-8 ]
YieldReaction ConditionsOperation in experiment
54.7%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; Inert atmosphere; Cooling with ice
Stage #2: for 4 h; Reflux; Inert atmosphere
Yield: 23.3-88.0percent .Take 3-(4-chlorophenyl)propan-1-ol (3c) for example. To a suspension of lithium aluminum hydride (1.71 g, 45 mmol) in THF (30 mL), under nitrogen atmosphere and ice bath, the solution of 2.74 g (15 mmol) 3-(4-chlorophenyl)acrylic acid (2c) in THF was gently added in 30 min. the resulting mixture stirred until it reached ambient temperature and then it was reflux for 4h. When TLC analyses indicated the disappearance of the starting material, after cooling to ambient temperature, 15 ml methanol and 15 ml water was dropped slowly to quench the reaction, then the PH was adjusted to 3 with 10percent hydrochloric acid, The crude mixture was extracted with ethyl acetate (3 × 30 ml), organic layer was combined and dried over anhydrous MgSO4 and concentrated in vacuo. The resulting yellow oil was purified by chromatography on silica-gel column (n-hexane: ethyl acetate = 4:1, v/v) to obtain the product, yellow oil, yield 54.7percent. 1H NMR (300 MHz, CDCl3) δ: 7.27-7.22(m, 2H), 7.15-7.10 (m, 2H), 3.66(t, J=6.4Hz, 2H), 2.68(t, J=7.44Hz, 2H), 1.91-1.81(m, 2H).
54.7% With lithium aluminium tetrahydride In tetrahydrofuran for 4.5 h; Inert atmosphere; Reflux; Cooling with ice General procedure: To a suspension of lithium aluminum hydride (1.71g, 45mmol) in THF (30mL), under nitrogen atmosphere and ice bath, the solution of 15mmol 3-(4-substituted phenyl)acrylic acid (2a-h) in THF was gently added in 30min. the resulting mixture stirred until it reached ambient temperature and then it was reflux for 4h. When TLC analyses indicated the disappearance of the starting material, after cooling to ambient temperature, 15ml methanol and 15ml water was dropped slowly to quench the reaction, then the PH was adjusted to 3 with 10percent hydrochloric acid, The crude mixture was extracted with ethyl acetate (3×30 ml), organic layer was combined and dried over anhydrous MgSO4 and concentrated in vacuo. The resulting yellow oil was purified by chromatography on silica-gel column (n-hexane: ethyl acetate = 4:1, v/v) to obtain the product.
Reference: [1] Chinese Chemical Letters, 2016, vol. 27, # 4, p. 555 - 558
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 7, p. 1849 - 1853
[3] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 18, p. 4752 - 4756
  • 3
  • [ 1615-02-7 ]
  • [ 6282-88-8 ]
  • [ 24583-70-8 ]
Reference: [1] Synthesis, 2011, # 9, p. 1375 - 1382
  • 4
  • [ 1615-02-7 ]
  • [ 14548-38-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 5, p. 1333 - 1336
[2] Patent: WO2017/150904, 2017, A1,
  • 5
  • [ 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
  • 6
  • [ 1615-02-7 ]
  • [ 19947-39-8 ]
Reference: [1] Australian Journal of Chemistry, 1997, vol. 50, # 6, p. 523 - 527
  • 7
  • [ 1615-02-7 ]
  • [ 64473-35-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 18, p. 4752 - 4756
  • 8
  • [ 2019-34-3 ]
  • [ 1615-02-7 ]
  • [ 18655-50-0 ]
Reference: [1] Patent: EP525360, 1993, A2,
  • 9
  • [ 1336-21-6 ]
  • [ 2019-34-3 ]
  • [ 1615-02-7 ]
  • [ 18655-50-0 ]
Reference: [1] Patent: US5242944, 1993, A,
  • 10
  • [ 1615-02-7 ]
  • [ 18655-50-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 1997, vol. 5, # 8, p. 1675 - 1683
  • 11
  • [ 1615-02-7 ]
  • [ 51301-86-1 ]
Reference: [1] Journal of Organic Chemistry, 1994, vol. 59, # 9, p. 2304 - 2313
  • 12
  • [ 1615-02-7 ]
  • [ 131690-60-3 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 40, p. 12977 - 12983
  • 13
  • [ 1615-02-7 ]
  • [ 14173-39-8 ]
  • [ 131690-60-3 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 40, p. 12977 - 12983
  • 14
  • [ 1615-02-7 ]
  • [ 14173-39-8 ]
  • [ 131690-60-3 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 40, p. 12977 - 12983
  • 15
  • [ 1615-02-7 ]
  • [ 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
  • 16
  • [ 1615-02-7 ]
  • [ 1028252-13-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 5, p. 1730 - 1752
  • 17
  • [ 1615-02-7 ]
  • [ 1251832-81-1 ]
Reference: [1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 14-15, p. 3255 - 3261
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