Structure of 2065-66-9
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CAS No. : | 2065-66-9 |
Formula : | C19H18IP |
M.W : | 404.22 |
SMILES Code : | C[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[I-] |
MDL No. : | MFCD00066175 |
InChI Key : | JNMIXMFEVJHFNY-UHFFFAOYSA-M |
Pubchem ID : | 638159 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 21 |
Num. arom. heavy atoms | 18 |
Fraction Csp3 | 0.05 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 105.03 |
TPSA ? Topological Polar Surface Area: Calculated from |
13.59 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.65 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.26 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.61 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
5.85 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.74 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.82 |
Log S (ESOL):? ESOL: Topological method implemented from |
-5.47 |
Solubility | 0.00138 mg/ml ; 0.00000342 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.26 |
Solubility | 0.0224 mg/ml ; 0.0000553 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-7.93 |
Solubility | 0.00000475 mg/ml ; 0.0000000117 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
Yes |
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) |
Yes |
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) |
Yes |
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 |
-5.74 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
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 |
2.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
4.53 |
* 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 |
---|---|---|
67% | Potassium tert-butoxide (24 gm, 0.22 moles) and triphenylphosphine methyl iodide (78 gm, 28.22 moles) were dissolved in dry tetrahydrofuran (150 ml). The mixture was cooled to -780C and stirred at the same temperature for about 15 minutes. Ethyl 4- oxocyclohexane carboxylate (25 gm, 0.147 moles) in tetrahydrofuran was added drop wise and the mixture was stirred at the same temperature for about 30 minutes and then it was warmed to room temperature and stirred overnight, extraction was done with ethyl acetate and water. The organic layer was dried over sodium sulfate and concentrated. Purification was done by column chromatography using 5% ethyl acetate in hexane. Yield: 19 gm (67%); m/z: (M++l) 169.26NMR: (delta, CDCl3) : 4.64 (2H, s), 4.09- 4.15 (2H, q), 2.42- 2.47 (IH, m), 2.31- 2.39 (2H, m), 1.96- 2.09 (4H, m), 1.43- 1.62 (2H, m), 1.23- 1.26 (3H, t) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.49 g | At first, KOBut (2.60 g, 19.3 mmol) was added to a solution of methyl triphenylphosphonium iodide (7.4 g, 23.2 mmol) in dry THF (50 mL) at -15 C and stirred for 3 h. A solution of crude aldehyde (1.88 g, 7.73 mmol) in THF (10 mL) was added dropwise and stirred for 5 h at room temperature. Saturated aqueous NH4Cl solution (30 mL) was added and extracted with EtOAc (3 × 40 mL). The organic layer was washed with water (50 mL), brine (50 mL), dried over Na2SO4, and evaporated on a rotavapor. The residue was purified by column chromatography (silica gel 60-120 mesh, EtOAc/hexane, 3:97) to furnish olefin 7 (1.49 g, 80%) as a pale yellow syrupy liquid. (c 1, CHCl3). IR (neat): numax 3448, 2977, 2931, 1697, 1454, 1386, 1253, 1175, 1092, 917, 850, 770 cm-1. 1H NMR (CDCl3, 400 MHz): delta 1.43-1.59 (m, 15H), 2.16-2.32 (m, 1H), 2.38-2.62 (m, 1H), 3.69-3.99 (m, 3H), 5.02-5.11 (m, 2H), 5.64, 5.82 (m, 1H). 13C NMR (CDCl3, 75 MHz): delta 23.67, 26.88, 28.24(×3), 37.40, 56.65, 66.22, 79.62, 93.46, 117.46, 134.42, 151.74. ESIMS: m/z 264 [M+Na]+. HRMS calcd for C13H23NO3Na: [M+Na]+ 264.1575, found: 264.1582. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.6% | With potassium tert-butylate; In N,N-dimethyl-formamide; at 20 - 50℃; for 17h;Inert atmosphere; | 4-(Di-p-tolylamino)benzaldehyde (1.8 g, 6 mmol) and methyltriphenylphosphonium iodide (2.7 g, 6.78 mmol) were dissolved in DMF (15 mL) and the solution was stirred at room temperature for 30 min under nitrogen atmosphere. Then potassium tert-butoxide (0.76 g, 6.78 mmol) was dissolved in DMF (20 mL) and added dropwise to the solution. The reaction mixture was stirred for 5 h atroom temperature, and then was heated to 50 °C for 12 h. After cooling to room temperature, the reaction mixture was extracte dwith dichloromethane and washed with dilute aqueous HCl solution. The organic phase was dried over anhydrous MgSO4, and then the solvent was removed by rotary evaporation. The crude product was purified using silica gel column chromatography (eluent:petroleum ether/dichloromethane = 5:1) to give 1.5 g 1 as a light yellow liquid (yield: 83.6percent). 1H NMR (CDCl3, 400 MHz, d/ppm): 7.24(d, 2H), 7.05-7.07 (d, 4H), 6.96-7.00 (m, 6H), 6.61-6.68 (dd, 1H), 5.59-5.63 (d, 1H), 5.11-5.14 (d, 1H), 2.31-2.35 (s, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Wittig Reaction (0166) To a solution of the Wittig salt from iodomethane (3.5 mmol) in anhydrous THF (10 mL) at -78 C. was added slowly n-BuLi (3 mL of a 1.5M solution in hexane, 3.0 mmol). After 45 min, a solution of B1 (3.5 mmol) in THF (10 mL) was added dropwise. The resulting solution was stirred for 40 min at -78 C. Then, the reaction mixture was allowed to reach room temperature and quenched with saturated NH4Cl solution. The aqueous phase was extracted with Et2O (3×30 mL), and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, and evaporated under reduced pressure. The crude was purified by column chromatography (hexane) on silica gel affording 1B (90%) as a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | Example 57 2-Chloro-4-methoxy-1-vinylbenzene To a suspension of phosphonium salt (2.05 g, 5 mmol) in THF (50 mL), was added t-BuOK (0.84 g, 7.5 mmol). The mixture turned to yellow and was kept stirring at RT for 1 h. 2-Chloro-4-methoxybenzaldehyde (0.85 g, 5 mmol) was added to the mixture. The mixture was stirred for 24 h, diluted with sat. NaHCO3 and then extracted with hexane. Organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by Isolera One (100percent hexanes to afford the desired product (0.45 g, 53percent yield). 1H NMR (CDCl3, delta): 7.49 (d, J=6.8 Hz, 1H), 7.03 (dd, J=8.8, 14.0 Hz, 1H), 6.90 (d, J=2.0, 1H), 6.79 (dd, J=2.0, 6.8 Hz, 1H), 5.62 (d, J=14.0 Hz, 1H), 5.26 (d, J=8.8 Hz, 1H), 3.80 (s, 3H). | |
53% | To a suspension of phosphonium salt (2.05 g, 5 mmol) in THF (50 mL), was added t-BuOK (0.84g, 7.5 mmol). The mixture turned to yellow and was kept stirring at RT for lh. 2-Chloro-4-methoxybenzaldehyde (0.85g, 5 mmol) was added tothe mixture. The mixture was stirred for 24h, diluted with sat. NaHCO3 and then extracted with hexane. Organic layer was dried over Na2504, filtered and concentrated in vacuo. The residue was purified by Isolera One (100percent hexanes to afford the desired product (0.45g, 53percent yield). ?H NMR (CDC13, oe): 7.49 (d, J 6.8Hz, 1H), 7.03 (dd, J 8.8, 14.0 Hz, 1H), 6.90 (d, J 2.0, 1H), 6.79 (dd, J 2.0, 6.8 Hz, 1H), 5.62 (d, J= 14.0Hz, 1H), 5.26 (d, J 8.8 Hz, 1H), 3.80 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65.75 g | With sodium t-butanolate; In toluene; at 25 - 55℃; | Example-1 Preparation of 4-(2,4-difluorophenyl)pent-4-enoic acid (Formula-2) To a mixture of <strong>[110931-77-6]4-(2,4-difluorophenyl)-4-oxobutanoic acid</strong> (100 g) and toluene (1000 ml), added methyl triphenylphosphine iodide (377.5 g) and sodium tertiary butoxide (183 g) at 25-30 C. Heated the reaction mixture to 50-55 C. and stirred for 6-8 hours at the same temperature. After completion of the reaction, cooled the reaction mixture to 25-30 C. Water was added to the reaction mixture and both organic and aqueous layers were separated. pH of aqueous layer was adjusted to 11 using 50% hydrochloric acid. Extracted the aqueous layer with toluene and washed the aqueous layer with dichloromethane. pH of the aqueous layer was further adjusted to 2.5 using 50% HCl and the reaction mixture was stirred for 45 minutes. Filtered the obtained solid, washed with water and then dried to get the title compound. Cyclohexane (500 ml) was added to the obtained solid and heated to 45-50 C. Carbon (10 g) was added to the reaction mixture and stirred for 15 minutes. Filtered the reaction mixture and washed with hot cyclohexane. Distilled off half of the solvent under reduced pressure. Cooled the reaction mixture to 10-15 C. and stirred for 60 minutes at the same temperature. Filtered the solid and washed with chilled cyclohexane and dried to get the title compound. Yield: 65.75 g |
95 g | With sodium t-butanolate; In dimethyl sulfoxide; at 10 - 30℃; for 2h; | Example-2: Preparation of 4-(2,4-difluorophenyl)pent-4-enoic acid (Formula-3)Methyl triphenylphoshonium iodide (220 gin) and dimethylsulfoxide.(500 ml) was added to <strong>[110931-77-6]4-(2,4-difluorophenyl)-4-oxobutanoic acid</strong> (100 gm) at 25-30C. Cooled the reaction mixture to 10-15C. Sodium tertiary butoxide (112 gin) was slowly added tothe reaction mixture at 10- 15C. Raised the temperature of the reaction mixture to 25-30C and stirred for 2 hours at thesame temperature. After completion of th reaction, cooled the reaction mixture to 10-1 5C Water was slowly added to the reaction mixture at 10-1 5C Further cooled the reaction mixture to 0-5C and stirred for 1 hour at the same temperature. Filtered the reaction mixture and washed with water. Heated the obtained filtrate to 25-30C and washed with dichioromethane. The aqueous layer and cooled to 0-5C. Adjusted the pH of the aqueous layer to 2-3 using dilutehydrochloric acid. Stirred the reaction mixture to 1 hour at 0-5C. Filtered the precipitated solid, washed with water. To the obtained wet compound, water was added at 25-30C and stirred for 45 minutes at the same temperature. Filtered the solid, washed with water and dried to get the title compound. Yield: 95 gin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With potassium tert-butylate; In tetrahydrofuran; at 20℃;Inert atmosphere; | A THF solution (40 mL) of 1 (0.81 g, 3.00 mmol)was added to a THF solution of potassium tert-butoxide(3.60 mL, 3.60 mmol) and methyl triphenyl phosphoniumiodide (1.46 g, 3.60 mmol). The solution was then stirredat room temperature for 4 h under nitrogen. The solutionwas poured into methylene chloride and washed withdistilled water. The organic layer was purified by columnchromatography on silica gel using n-hexane as an eluent.After removal of the solvent, the residue was precipitatedin methanol to give 2 as a white solid. Yield (630 mg,78%). mp 120-122 C. 1H NMR (400 MHz, DMSO-d6) 5.38 (d, 1 H, -CH CH2), 5.96 (d, 1 H, -CH CH2),6.88 (dd, 1 H, -CH CH2), 7.28 (t, 2 H, -Ph-carbazole),7.42 (m, 4 H, -Ph-carbazole), 7.60 (d, 2 H, -carbazole-Ph), 7.76 (d, 2 H, -carbazole-Ph), 8.24 (d, 2 H, -Ph-carbazole); 13C NMR (100.64 MHz, DMSO-d6) 115.08,120.67, 125.51, 125.82, 126.06, 128.16, 131.68, 132.18,133.23, 141.26, 141.78, 145.44. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; | Ph3P (94.4mg, 0.36mmol) and <strong>[1088-00-2]9-phenyl-9-phosphafluorene</strong> (93.6mg, 0.36mmol) were dissolved in dry THF (3mL) under nitrogen in a 10mm NMR tube. The solution was cooled to 0C and DIAD (18μL, 0.09mmol) then added dropwise over 1min to the swirled, cooled solution. A cap was placed on the tube and sealed with Parafilm before recording the 31P NMR spectrum at 10C on a 300MHz instrument within 5min. The experiment was repeated using methyl iodide in place of DIAD. All spectra were acquired at an operating frequency of 121.47MHz using a 45 flip angle, 3s recycle delay, and a 0.33s acquisition time with gated decoupling. Negative 31P chemical shifts are upfield of external phosphoric acid (85%). |
Tags: 2065-66-9 synthesis path| 2065-66-9 SDS| 2065-66-9 COA| 2065-66-9 purity| 2065-66-9 application| 2065-66-9 NMR| 2065-66-9 COA| 2065-66-9 structure
A1228280 [81826-67-7]
(Methyl-13C)triphenylphosphonium iodide
Reason: Stable Isotope
Precautionary Statements-General | |
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Code | Phrase |
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H202 | Explosive; severe projection hazard |
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H220 | Extremely flammable gas |
H221 | Flammable gas |
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H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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