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[ CAS No. 31465-36-8 ] {[proInfo.proName]}

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Chemical Structure| 31465-36-8
Chemical Structure| 31465-36-8
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Product Details of [ 31465-36-8 ]

CAS No. :31465-36-8 MDL No. :MFCD00044105
Formula : C13H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :VTYZDTAGEMAJMM-UHFFFAOYSA-N
M.W : 215.25 Pubchem ID :101402
Synonyms :

Calculated chemistry of [ 31465-36-8 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.08
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 63.85
TPSA : 44.48 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.44
Log Po/w (XLOGP3) : 2.01
Log Po/w (WLOGP) : 3.08
Log Po/w (MLOGP) : 2.34
Log Po/w (SILICOS-IT) : 2.32
Consensus Log Po/w : 2.44

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.8
Solubility : 0.343 mg/ml ; 0.00159 mol/l
Class : Soluble
Log S (Ali) : -2.57
Solubility : 0.578 mg/ml ; 0.00268 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.43
Solubility : 0.008 mg/ml ; 0.0000372 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.65

Safety of [ 31465-36-8 ]

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 [ 31465-36-8 ]

* 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 [ 31465-36-8 ]
  • Downstream synthetic route of [ 31465-36-8 ]

[ 31465-36-8 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 6337-24-2 ]
  • [ 31465-36-8 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen In ethyl acetate for 18 h; Step 2.
4-(4-Methoxyphenoxy)aniline
To a solution of 1-methoxy-4-(4-nitrophenoxy)benzene (12.0 g, 49 mmol) in EtOAc (250 mL) was added 5percent Pt/C (1.5 g) and the resulting slurry was shaken under a H2 atmosphere (50 psi) for 18 h.
The reaction mixture was filtered through a pad of Celite.(R). with the aid of EtOAc and concentrated in vacuo to give an oil which slowly solidified (10.6 g, 100percent): 1H-NMR (CDCl3) δ 3.54 (br s, 2H), 3.78 (s, 3H), 6.65 (d, J=8.8 Hz, 2H), 6.79-6.92 (m, 6H); EI-MS m/z 215 (M+).
100% With hydrogen In ethyl acetate for 18 h; To a solution of 1-methoxy-4-(4-nitrophenoxy)benzene (12.0 g, 49 mmol) in EtOAc (250 mL) was added 5percent Pt/C (1.5 g) and the resulting slurry was shaken under a H2 atmosphere (50 psi) for 18 h. The reaction mixture was filtered through a pad of Celite with the aid of EtOAc and concentrated in vacuo to give an oil which slowly solidified (10.6 g, 100percent): 1H-NMR (CDCl3) ? 3.54 (br s, 2H), 3.78 (s, 3H), 6.65 (d, J=8.8 Hz, 2H), 6.79-6.92 (m, 6H); EI-MSm/z 215 (M+).
100% With hydrogen In ethyl acetate for 18 h; Step 2. 4-(4-Methoxyphenoxy)aniline; To a solution of 1-methoxy-4-(4-nitrophenoxy)benzene (12.0 g, 49 mmol) in EtOAc (250 mL) was added 5percent Pt/C (1.5 g) and the resulting slurry was shaken under a H2 atmosphere (50 psi) for 18 h. The reaction mixture was filtered through a pad of Celite.(R). with the aid of EtOAc and concentrated in vacuo to give an oil which slowly solidified (10.6 g, 100percent): 1H-NMR (CDCl3) δ 3.54 (br s, 2H), 3.78 (s, 3H), 6.65 (d, J=8.8 Hz, 2H), 6.79-6.92 (m, 6H); EI-MS m/z 215 (M+).
100% With hydrogen In ethyl acetate for 18 h; Step 2. 4-(4-Methoxyphenoxy)aniline; To a solution of 1-methoxy-4-(4-nitrophenoxy)benzene (12.0 g, 49 mmol) in EtOAc (250 mL) was added 5percent Pt/C (1.5 g) and the resulting slurry was shaken under a H2 atmosphere (50 psi) for 18 h. The reaction mixture was filtered through a pad of Celite.(R). with the aid of EtOAc and concentrated in vacuo to give an oil which slowly solidified (10.6 g, 100percent): 1H-NMR (CDCl3) δ 3.54 (br s, 2H), 3.78 (s, 3H), 6.65 (d, J=8.8 Hz, 2H), 6.79-6.92 (m, 6H); EI-MS m/z 215 (M+).
100% With hydrogen In ethyl acetate for 18 h; Step 2.
4-(4-Methoxyphenoxy)aniline

To a solution of 1-methoxy-4-(4-nitrophenoxy)benzene (12.0 g, 49 mmol) in EtOAc (250 mL) was added 5percent Pt/C (1.5 g) and the resulting slurry was shaken under a H2 atmosphere (50 psi) for 18 h.
The reaction mixture was filtered through a pad of Celite.(R). with the aid of EtOAc and concentrated in vacuo to give an oil which slowly solidified (10.6 g, 100percent): 1H-NMR (CDCl3) δ 3.54 (br s, 2H), 3.78 (s, 3H), 6.65 (d, J=8.8 Hz, 2H), 6.79-6.92 (m, 6H); EI-MS m/z 215 (M+).
100% With hydrogen In ethyl acetate for 18 h; Step 2.
4-(4-Methoxyphenoxy)aniline
To a solution of 1-methoxy-4-(4-nitrophenoxy)benzene (12.0 g, 49 mmol) in EtOAc (250 mL) was added 5percent Pt/C (1.5 g) and the resulting slurry was shaken under a H2 atmosphere (50 psi) for 18 h.
The reaction mixture was filtered through a pad of Celite.(R). with the aid of EtOAc and concentrated in vacuo to give an oil which slowly solidified (10.6 g, 100percent): 1H-NMR (CDCl3) δ 3.54 (br s, 2H), 3.78 (s, 3H), 6.65 (d, J 8.8 Hz, 2H), 6.79-6.92 (m, 6H); EI-MS m/z 215 (M+).
100% With hydrogen In ethyl acetate for 18 h; To a solution of 1-methoxy-4-(4-nitrophenoxy)benzene (12.0 g, 49 mmol) in EtOAc (250 mL) was added 5percent Pt/C (1.5 g) and the resulting slurry was shaken under a H2 atmosphere (50 psi) for 18 h.
The reaction mixture was filtered through a pad of Celite.(R). with the aid of EtOAc and concentrated in vacuo to give an oil which slowly solidified (10.6 g, 100percent): 1H-NMR (CDCl3) δ 3.54 (br s, 2H), 3.78 (s, 3H), 6.65 (d, J=8.8 Hz, 2H), 6.79-6.92 (m, 6H); EI-MSm/z 215 (M+).
73% at 90℃; for 0.333333 h; General procedure: To a solution of 2{1,1}(2.90 g, 10.2 mmol) in AcOH (15 mL) was added Fe powder (2.86 g, 51.0 mmol) and the mixture was heated at 90 °C for 20 min. Then the reaction mixture was cooled to rt and poured into ice water followed by neutralization with saturated NaHCO3 solution. The precipitated solid was separated by filtration through a Celite bed which was repeatedly washed with EtOAc (4 x 10 mL). The organic layer was pooled, washed with brine (50 mL), dried (Na2SO4) and concentrated to obtain a residue. Crystallization of the residue from EtOAc-Hexanes furnished the pure products 3{1,1} as a white solid (1.8 g, 70percent).

Reference: [1] Patent: US2008/269265, 2008, A1, . Location in patent: Page/Page column 14
[2] Patent: EP1449834, 2004, A2, . Location in patent: Page 22
[3] Patent: EP1042305, 2005, B1, . Location in patent: Page/Page column 27
[4] Patent: US2007/244120, 2007, A1, . Location in patent: Page/Page column 17
[5] Patent: US2003/207914, 2003, A1, . Location in patent: Page/Page column 8
[6] Patent: US2012/46290, 2012, A1, . Location in patent: Page/Page column 17
[7] Patent: EP1047418, 2005, B1, . Location in patent: Page/Page column 28
[8] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 7, p. 1719 - 1723
[9] Journal of the American Chemical Society, 1938, vol. 60, p. 94
[10] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1931, vol. 201, p. 142,146
[11] Monatshefte fuer Chemie, 1931, vol. 57, p. 31,38
[12] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1978, vol. 16, p. 810 - 814
[13] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 4, p. 1023 - 1026
[14] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 16, p. 4477 - 4492
[15] Chemical Communications, 2005, # 19, p. 2486 - 2488
[16] Patent: WO2005/35507, 2005, A2, . Location in patent: Page/Page column 59-60
[17] Patent: US2002/65296, 2002, A1,
[18] Patent: US2004/102636, 2004, A1,
[19] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 14, p. 3895 - 3898
[20] Patent: WO2006/99231, 2006, A1, . Location in patent: Page/Page column 44-45
[21] Letters in Drug Design and Discovery, 2012, vol. 9, # 4, p. 379 - 388
[22] Asian Journal of Chemistry, 2013, vol. 25, # 7, p. 3863 - 3866
[23] MedChemComm, 2015, vol. 6, # 4, p. 671 - 676
  • 2
  • [ 150-76-5 ]
  • [ 31465-36-8 ]
Reference: [1] Chemical Communications, 2005, # 19, p. 2486 - 2488
[2] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 16, p. 4477 - 4492
[3] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 4, p. 1023 - 1026
[4] Letters in Drug Design and Discovery, 2012, vol. 9, # 4, p. 379 - 388
[5] Asian Journal of Chemistry, 2013, vol. 25, # 7, p. 3863 - 3866
[6] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 7, p. 1719 - 1723
[7] MedChemComm, 2015, vol. 6, # 4, p. 671 - 676
  • 3
  • [ 350-46-9 ]
  • [ 31465-36-8 ]
Reference: [1] Chemical Communications, 2005, # 19, p. 2486 - 2488
[2] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 16, p. 4477 - 4492
[3] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 4, p. 1023 - 1026
[4] Letters in Drug Design and Discovery, 2012, vol. 9, # 4, p. 379 - 388
[5] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 7, p. 1719 - 1723
[6] MedChemComm, 2015, vol. 6, # 4, p. 671 - 676
  • 4
  • [ 459-60-9 ]
  • [ 31465-36-8 ]
Reference: [1] Chemical Communications, 2005, # 19, p. 2486 - 2488
  • 5
  • [ 100-02-7 ]
  • [ 31465-36-8 ]
Reference: [1] Chemical Communications, 2005, # 19, p. 2486 - 2488
  • 6
  • [ 459-60-9 ]
  • [ 123-30-8 ]
  • [ 31465-36-8 ]
Reference: [1] Chemical Communications, 2005, # 19, p. 2486 - 2488
  • 7
  • [ 150-76-5 ]
  • [ 371-40-4 ]
  • [ 31465-36-8 ]
Reference: [1] Chemical Communications, 2005, # 19, p. 2486 - 2488
  • 8
  • [ 150-76-5 ]
  • [ 106-40-1 ]
  • [ 31465-36-8 ]
Reference: [1] Synlett, 2011, # 2, p. 268 - 272
  • 9
  • [ 1122-93-6 ]
  • [ 31465-36-8 ]
Reference: [1] Monatshefte fuer Chemie, 1931, vol. 57, p. 31,38
[2] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1931, vol. 201, p. 142,146
[3] Journal of the American Chemical Society, 1938, vol. 60, p. 94
  • 10
  • [ 100-00-5 ]
  • [ 31465-36-8 ]
Reference: [1] Monatshefte fuer Chemie, 1931, vol. 57, p. 31,38
[2] Journal of the American Chemical Society, 1938, vol. 60, p. 94
[3] Asian Journal of Chemistry, 2013, vol. 25, # 7, p. 3863 - 3866
  • 11
  • [ 150-76-5 ]
  • [ 350-46-9 ]
  • [ 31465-36-8 ]
Reference: [1] Patent: US2012/46290, 2012, A1,
[2] Patent: EP1047418, 2005, B1,
  • 12
  • [ 67-56-1 ]
  • [ 139-59-3 ]
  • [ 31465-36-8 ]
Reference: [1] Gazzetta Chimica Italiana, 1985, vol. 115, # 6, p. 343 - 346
  • 13
  • [ 586-78-7 ]
  • [ 31465-36-8 ]
Reference: [1] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1931, vol. 201, p. 142,146
  • 14
  • [ 31465-36-8 ]
  • [ 65948-19-8 ]
  • [ 129121-43-3 ]
Reference: [1] Patent: US5002942, 1991, A,
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