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[ CAS No. 1849-36-1 ] {[proInfo.proName]}

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Chemical Structure| 1849-36-1
Chemical Structure| 1849-36-1
Structure of 1849-36-1 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations

?ukasz Gutowski ; Malwina Liszewska ; Bartosz Bartosewicz , et al. DOI: PubMed ID:

Abstract: Surface-enhanced Raman spectroscopy (SERS) and self-assembled monolayer (SAM) approaches were used to investigate the reactions of organic monoradicals with methanol. An attempt was made to generate monoradicals from thiophenols and phenylmethanethiols substituted with bromine, iodine, and nitro groups by irradiation with UV light. Monolayers of radical precursors were deposited on SERS substrates, which were then immersed in methanol and irradiated for 1 and/or 3, 6, 12 and 24 h in a UV photochemical reactor. Pre- and postreaction SERS spectra were obtained by using a confocal Raman microscope and compared with the spectra of expected products of the radical reaction with methanol. Our studies have shown that the efficiency of monoradical generation is highly dependent on the chemical structure of the precursor. In addition, it is shown that both the SERS substrate and experimental conditions used strongly influence the obtained results.

Keywords: SERS ; SERS substrates ; Self-assembled monolayer ; Reactive intermediates ; Organic monoradicals ; Reactivity

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Product Details of [ 1849-36-1 ]

CAS No. :1849-36-1 MDL No. :MFCD00007343
Formula : C6H5NO2S Boiling Point : -
Linear Structure Formula :NO2(C6H4)SH InChI Key :AXBVSRMHOPMXBA-UHFFFAOYSA-N
M.W : 155.17 Pubchem ID :15809
Synonyms :

Calculated chemistry of [ 1849-36-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 42.52
TPSA : 84.62 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.67 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.12
Log Po/w (XLOGP3) : 2.22
Log Po/w (WLOGP) : 1.88
Log Po/w (MLOGP) : 1.11
Log Po/w (SILICOS-IT) : -0.03
Consensus Log Po/w : 1.26

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.58
Solubility : 0.409 mg/ml ; 0.00264 mol/l
Class : Soluble
Log S (Ali) : -3.63
Solubility : 0.0362 mg/ml ; 0.000233 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.87
Solubility : 2.07 mg/ml ; 0.0134 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.71

Safety of [ 1849-36-1 ]

Signal Word:Danger Class:9
Precautionary Statements:P264-P270-P280-P301+P312-P305+P351+P338-P310-P330-P501 UN#:3335
Hazard Statements:H302-H318 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1849-36-1 ]

* 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 [ 1849-36-1 ]
  • Downstream synthetic route of [ 1849-36-1 ]

[ 1849-36-1 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 36684-47-6 ]
  • [ 1849-36-1 ]
  • [ 431980-38-0 ]
YieldReaction ConditionsOperation in experiment
63% With potassium carbonate; ethylene glycol In isopropyl alcohol at 20℃; for 1 h; microwave irradiation Method A: Synthesis of 2-(4-Nitrophenylthio)-N-(2-methoxyphenyl)benzamide (1) Vif inhibitor 1 was synthesized using the procedure outlined in Scheme 9. The key step in this reaction scheme is the copper catalyzed coupling reaction of 2-iodo-N-(2-methoxyphenyl)benzamide 3 with 4-nitrothiophenol 4 by microwave irradiation. The intermediate compound 3 was obtained in excellent yield by the reaction of 2-methoxyaniline 5 with 2-iodobezoyl chloride 2. Scheme 9: (a) Et3N, CH2Cl2, 0° C. to r. t. overnight, 98percent; (b) K2CO3, Cu(I)I (cat.), HOCH2CH2OH, 2-propanol, microwave-150 W, 80° C., 30 min (2.x.), 63percent. 2-(4-Nitrophenylthio)-N-(2-methoxyphenyl)benzamide (1) 2-Iodo-N-(2-methoxyphenyl)benzamide 3 (0.355 g, 1.0 mmol), Cu(I) iodide (20 mg, 0.1 mmol), K2CO3 (0.276 g, 2.0 mmol), and 4-nitrothiophenol (0.155 g, 1 mmol) were added to a 10 mL reaction vessel with Teflon-lined septum. The tube was evacuated and backfilled with dry N2 (3 cycles). Ethylene glycol (0.1 mL, 2.0 mmol) and 2-propanol (1 mL) were added by syringe at room temperature. The reaction vessel was heated in a microwave reactor (CEM, Explorer) at 80° C. and 150 W power for 30 min (2.x.). The reaction mixture was then allowed to reach room temperature. Ethyl acetate (approx. 10 mL) was added; the reaction mixture was filtered and concentrated. The crude product was purified by flash column chromatography on silica, eluting with 20percent EtOAc in hexanes. This procedure provided 2-(4-nitrophenylthio)-N-(2-methoxyphenyl)benzamide 1 as pale yellow crystalline solid (0.24 g, 63percent); 1H NMR (400 MHz, CDCl3) δ 8.40 (d, J=8.0 Hz, 1H), 8.39 (s, 1H, overlapping signal), 8.05 (ddd, J=9.2, 2.4, 1.6 Hz, 2H), 7.77 (dd, J=6.4, 2.4 Hz, 1H), 7.56-7.49 (m, 3H), 7.29-7.25 (m, 2H), 7.06 (ddd, J=9.2, 7.6, 1.6 Hz, 1H), 6.95 (dt, J=8.8, 0.8, 1.2 Hz, 1H), 6.85 (dd, J=8.0, 0.8 Hz, 1H), 3.78 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 165.44, 148.22, 146.87, 146.15, 140.63, 135.76, 131.66, 130.09, 129.87, 129.49, 128.79 (2C), 127.54, 124.54, 124.35 (2C), 121.37, 120.05, 110.19, 55.88; MS (ESI): m/z 402.99 (M+Na)+.
Reference： [1] Patent: US2007/99919, 2007, A1, . Location in patent: Page/Page column 26; 27
[2] ChemMedChem, 2012, vol. 7, # 7, p. 1217 - 1229
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