Structure of 13329-40-3
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CAS No. : | 13329-40-3 |
Formula : | C8H7IO |
M.W : | 246.05 |
SMILES Code : | CC(C1=CC=C(I)C=C1)=O |
MDL No. : | MFCD00045320 |
InChI Key : | JZJWCDQGIPQBAO-UHFFFAOYSA-N |
Pubchem ID : | 72869 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 49.35 |
TPSA ? Topological Polar Surface Area: Calculated from |
17.07 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.39 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.49 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.67 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.12 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.53 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.25 |
Solubility | 0.139 mg/ml ; 0.000563 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.39 |
Solubility | 1.0 mg/ml ; 0.00408 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.69 |
Solubility | 0.0504 mg/ml ; 0.000205 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.1 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.6 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With potassium hydroxide In dimethyl sulfoxide at 120℃; Inert atmosphere | General procedure: A mixture of amine (2.0 mmol), aryl halides (1.0 mmol), catalyst (1.0 molpercent Pd), and DMSO (6 ml) was stirred for 16 h under nitrogen atmosphere at 120 ◦C. The progress of reaction was monitored by gas chromatography. After completion, the reaction mixture was cooled and filtered to remove the catalyst which could be used for further reaction. The filtrate obtained was purified by flash column chromatography on silica gel to afford the desired product, which was confirmed by GC–MS. All the prepared compounds are known and compared with authentic samples. |
83 %Chromat. | With C35H34N3OP2PdS(1+)*NO3(1-); sodium t-butanolate In 1,4-dioxane at 100℃; for 7 h; | General procedure: In a typical run, an oven-dried 10 ml round bottom flask was charged with a known mole percent of catalyst, NaOtBu (1.3 mmol), amine (1.2 mmol) and aryl halide (1 mmol) with the appropriate solvent(s) (4 ml). The flask was placed in a preheated oil bath at required temp. After the specified time the flask was removed from the oil bath, water (20 ml) was added, and extraction with ether (4×10 ml) was done. The combined organic layers were washed with water (3×10 ml), dried over anhydrous Na2SO4, and filtered. Solvent was removed under vacuum. The residue was dissolved in acetonitrile and analyzed by GC–MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 80℃; under 760.051 Torr; for 6h; | General procedure: The catalytic reactions were carried out in a 10 mL reaction flask and fitted with condenser and carbon monoxide balloon. In a typical run, a catalyst containing 1.0 mol% Pd, aryl iodide (0.5 mmol) and DBU (1.5 mmol) were added to solvent and allowed to react under CO atmosphere at 80 C temperature for 6-10 h. After the reaction,the flask was cooled to room temperature and carbon monoxide balloon was removed. The reaction mixture was then centrifuged and the clear supernatant was analyzed with GC by using n-butanol as an internal standard. For the study of substrate scope, after completion of the reaction, the catalyst was centrifuged and extracted with copious ethanol. The obtained liquid was concentrated. For phenoxycarbonylation, the obtained liquid was diluted with saturated NH4Cl and extracted with diethyl ether. The organic layer was dried over anhydrous Na2SO4 and then concentrated. The product was obtained by preparative thin-layer chromatography (PTLC) using petroleum ether and ethyl acetate (30:1, v/v) as eluting solvent. The purity of products was checked by NMR and yields were based on aryl iodides. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.7% | With potassium hydroxide; In ethanol; water; at 20℃; for 3.0h; | Synthesis of 3-(5-dimethylamino-2-thienyl)-1-(4-iodophenyl)-prop-2-en-1-one (33) 4-Iodoacetophenone (246 mg, 1.00 mmol) and Compound 30 (155 mg, 1.00 mmol) were dissolved in ethanol (5 mL), followed by addition of 10% aqueous potassium hydroxide (7.5 mL). The mixture was reacted at room temperature for 3 h, the layers were separated with ethyl acetate (50 mL x 2), and the ethyl acetate layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to medium-pressure preparative chromatography using ethyl acetate/hexane (1/4) as an elution solvent to obtain Compound 33. Yield 18 mg (yield rate 4.7%). 1H NMR (300 MHz, CDCl3) delta 3.04 (s, 6H), 5.22 (d, J = 3.9 Hz, 1H), 6.80 (d, J = 3.6 Hz, 1H), 6.89 (d, J = 15.0 Hz, 1H), 7.46 (d, J = 14.7 Hz, 1H), 7.70 (d, J = 8.1 Hz, 2H), 7.81 (d, J = 8.7 Hz, 2H). MS m/z 383 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.7% | In ethanol; hexane; ethyl acetate; | Synthesis of 3-(5-dimethylamino-2-thienyl)-1-(4-iodophenyl)-prop-2-en-1-one (33) 4-Iodoacetophenone (246 mg, 1.00 mmol) and Compound 30 (155 mg, 1.00 mmol) were dissolved in ethanol (5 mL), followed by addition of 10% aqueous potassium hydroxide (7.5 mL). The mixture was reacted at room temperature for 3 h, the layers were separated with ethyl acetate (50 mL*2), and the ethyl acetate layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to medium-pressure preparative chromatography using ethyl acetate/hexane (1/4) as an elution solvent to obtain Compound 33. Yield 18 mg (yield rate 4.7%). 1H NMR (300 MHz, CDCl3) delta 3.04 (s, 6H), 5.22 (d, J=3.9 Hz, 1H), 6.80 (d, J=3.6 Hz, 1H), 6.89 (d, J=15.0 Hz, 1H), 7.46 (d, J=14.7 Hz, 1H), 7.70 (d, J=8.1 Hz, 2H), 7.81 (d, J=8.7 Hz, 2H). MS m/z 383 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With C35H20F34NO3(1-)*Pd(2+)*Cl(1-); N-ethyl-N,N-diisopropylamine; In neat (no solvent); at 130℃; for 0.283333h;Microwave irradiation; | General procedure: A mixture of the aryl halide (1.0 mmol), alcohol (5.0 equiv), Mo(CO)6 (0.5 equiv), DIPEA (1.5 equiv) and palladacycle 1 (1 mol % Pd) was heated in a pressure tube at 130 C under microwave irradiation. The reaction was monitored by TLC. When the reaction has completed, the reaction mixture was cooled to room temperature and the alcohol was removed. The crude mixture was subjected to F-SPE to remove palladacycle 1 (see general procedure for the recycling of palladacycle 1) and the solution of crude product was concentrated, diluted with EtOAc (20 mL) and washed successively with 2 M HCl (210 mL) and water (10 mL). The organic layer was driedover anhydrous MgSO4, filtered and concentrated to give pure 6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With acetic acid; In ethanol;Reflux; | General procedure: 6-Fluoro-2-[2-(1-(substituted phenyl)ethylidene)hydraizno]benzothiazoles 7a-d. General Procedure E. A mixture of compound 2 (0.183 g, 0.001 mol), the appropriate acetophenone (0.001 mol) and glacial acetic acid (0.1 mL) in ethanol (20 mL) was heated at reflux temperature for 6-8 h. On cooling, the precipitated solid was collected by filtration, washed with ethanol, dried and crystallized from ethyl acetate : ethanol (3:1) to furnish compounds 7a-d. |
Tags: 13329-40-3 synthesis path| 13329-40-3 SDS| 13329-40-3 COA| 13329-40-3 purity| 13329-40-3 application| 13329-40-3 NMR| 13329-40-3 COA| 13329-40-3 structure
A290841 [6136-66-9]
(4-Iodophenyl)(phenyl)methanone
Similarity: 0.95
A261860 [340825-13-0]
6-Iodo-3,4-dihydronaphthalen-1(2H)-one
Similarity: 0.90
A290841 [6136-66-9]
(4-Iodophenyl)(phenyl)methanone
Similarity: 0.95
A261860 [340825-13-0]
6-Iodo-3,4-dihydronaphthalen-1(2H)-one
Similarity: 0.90
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