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CAS No. : | 24470-78-8 | MDL No. : | MFCD00031595 |
Formula : | C21H22IP | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HHBXWXJLQYJJBW-UHFFFAOYSA-M |
M.W : | 432.28 | Pubchem ID : | 2723783 |
Synonyms : |
|
Num. heavy atoms : | 23 |
Num. arom. heavy atoms : | 18 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 114.65 |
TPSA : | 13.59 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.34 cm/s |
Log Po/w (iLOGP) : | 4.67 |
Log Po/w (XLOGP3) : | 5.06 |
Log Po/w (WLOGP) : | 1.39 |
Log Po/w (MLOGP) : | 6.28 |
Log Po/w (SILICOS-IT) : | 5.31 |
Consensus Log Po/w : | 4.54 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -6.02 |
Solubility : | 0.00041 mg/ml ; 0.000000948 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -5.09 |
Solubility : | 0.00354 mg/ml ; 0.00000818 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -8.35 |
Solubility : | 0.00000191 mg/ml ; 0.0000000044 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 4.62 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
83% | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; cyclohexane at 0℃; for 1h; Inert atmosphere; Stage #2: tetrahydro-2H-2-pyranol In tetrahydrofuran; cyclohexane at 20℃; for 4h; Inert atmosphere; | |
48% | With potassium hydride In tetrahydrofuran for 3h; Heating; | |
With methyllithium In diethyl ether |
With potassium hexamethylsilazane In tetrahydrofuran at 0 - 20℃; | ||
1.39 g | With potassium <i>tert</i>-butylate In tetrahydrofuran at 23℃; for 23h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium In tetrahydrofuran at -15℃; for 0.5h; | ||
0.825 g | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: 4-chlorobutyraldehyde In tetrahydrofuran at 0 - 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2h; Stage #2: 2-(3-methoxyphenyl)acetaldehyde In tetrahydrofuran; hexane at 20℃; | |
With n-butyllithium 1) THF, 2) THF, 4h; Yield given. Multistep reaction; | ||
Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2h; Inert atmosphere; Stage #2: 2-(3-methoxyphenyl)acetaldehyde In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With n-butyllithium In tetrahydrofuran; hexane at 0℃; | |
58% | With n-butyllithium In tetrahydrofuran 0 deg C to rt; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium 1) THF, hexane, 15 min, 2) 1h; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66.7% | Stage #1: isopropyltriphenylphosphonium iodide With sodium hydride In dimethyl sulfoxide; mineral oil at 50℃; for 0.75h; Inert atmosphere; Stage #2: cyclohexanedione monoethylene ketal In dimethyl sulfoxide; mineral oil at 50℃; for 16.75h; | 1 Exam le 1 : Synthesis of Jso-PGH The reaction scheme is the following: Preparation of 44wp pyHdet -l, 4^tima-tipim{ 4, SJ eca (2) : isopropyltriphenylphosphonium iodide (83.02 g, 1 2 lnmol) was added to NaH (60%, in mineral oil, 8.38 g, 1 2 mmol) in dry dimethyl sulfoxide (120 mL) at room temperature under a nitrogen atmosphere. The reaction mixture was slowly heated to 50 "C over a period of 15 min and maintained at 50 °C until the reaction mass became a red color (approximately 30 min). A solution of 1 ,4-cyclohexaned.ione monoethytene ketal (1 , 30 g, 192 mmol) in dry dimethyl sulfoxide was added over a period of 45 min while keeping the temperature below 50 °C and the reaction was maintained at 50 "C for 16 h. The reaction mixture was cooled to room temperature, quenched with cold water (1 0 ml), and extracted with ethyl acetate (2x 160 mL). The combined organic layer was washed with water (2*200 mL), followed by brine (10%, 250 mL) and dried over sodium sulfate. The filtered organic layer was concentrated to give a solid which was triturated with hexanes (300 mL) and the precipitated triphenylphosphine oxide was filtered off. The hexane layer was concentrated to give an oil which was purified by column chromatography. [Column dimensions: dia: 6.0 cm, height: 12 cm, silica: 200 mesh, eluted hexanes (1.0 L) followed by hexane: ethyl acetate (97:3, 2.0 L)] The hexane: ethyl acetate fractions were combined and concentrated under vacuum to give an oil. Weight: 23.36 g. Weight yield: 66.7%. 'H-NMR (400 MHz, CDCb): |
60% | With sodium hydride In dimethyl sulfoxide at 50℃; for 16h; | |
With n-butyllithium 1.) ether, 0 degC, 30 min then room t.; 2.) 0 degC, 1 h then warning up; Yield given. Multistep reaction; |
Stage #1: isopropyltriphenylphosphonium iodide With sodium hydride In dimethyl sulfoxide; mineral oil at 50℃; Stage #2: cyclohexanedione monoethylene ketal In dimethyl sulfoxide; mineral oil at 50℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; cyclohexane at -78 - 0℃; for 0.5h; Inert atmosphere; Stage #2: ethyl cinnamate In tetrahydrofuran; cyclohexane at -78 - 20℃; | General Procedure A: Cyclopropanation of α,β-unsaturated esters General procedure: To a suspension of the phosphonium halide (A4) (1.2 equiv.) in anhydrous THF (0.3 M) at -78°C was added n-BuLi (2.0 M in cyclohexane, 1.1 equiv.) under an nitrogen atmosphere. The resulting mixture was warmed to 0°C and stirred for 30 min. The reaction mixture was cooled to -78°C followed by the addition of a solution of the α,β -unsaturated ester (A3) (1.0 equiv.) in anhydrous THF (0.5 M). The reaction mixture was stirred for 2 h at 0°C, then slowly warmed to ambient temperature and stirred overnight. The solution was poured onto IN HC1. The aqueous layer was extracted with ethyl acetate and the combined organic layers were sequentially washed with saturated NaHC03, brine, dried over Na2S04, and concentrated in vacuo. The crude cyclopropane was purified by column chromatography to furnish the pure cyclopropyl ester (A5). |
Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: ethyl cinnamate In tetrahydrofuran; hexane at 0 - 25℃; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With n-butyllithium In tetrahydrofuran at -78 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: 2-bromo-5-fluorobenzaldehyde In tetrahydrofuran; hexane at 0℃; | |
Stage #1: isopropyltriphenylphosphonium iodide With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; Stage #2: 2-bromo-5-fluorobenzaldehyde In tetrahydrofuran Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: 6-bromo-3,4-methylenedioxybenzaldehyde In tetrahydrofuran; hexane at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: triphenyl(propan-2-yl)phosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; Stage #2: ortho-bromobenzaldehyde In tetrahydrofuran; hexane at 0 - 20℃; for 2h; | 4.3.15. 1-Bromo-2-(2-methylprop-1-en-1-yl)benzene (36). In a procedure adapted from Liu et al.,43 to a solution of isopropyltriphenylphosphoniumiodide (3.86 g, 8.92 mmol) in THF(50 mL) at 0 C was added n-BuLi (2.5 M in hexanes, 3.73 mL,9.32 mmol) dropwise. The reaction mixture was maintained at 0 C and 2-bromobenzaldehyde (35) (0.95 mL, 8.11 mmol) was added dropwise. The solution was allowed to warm to room temperature over 2 h, before the reaction mixture was diluted with hexane (15 mL). The reaction mixturewas then filtered through a silica plug and the solvent removed in vacuo to afford the product as a clear oil (1.71 g, quant.), with spectral data in accordance with the literature.44 Rf 0.55 (hexane).1H NMR (CDCl3) d: 7.56 (d, J7.6 Hz, 1H),7.28e7.21 (m, 2H), 7.06 (m, 1H), 6.24 (m, 1H), 1.93 (d, J1.2 Hz, 3H),1.75 (d, J1.2 Hz, 3H). LRMS (EI): m/z 212.0 [M] (81Br, 13%), 210.0[M] (79Br, 13%), 169.0 [MC3H5] (100%). |
89% | Stage #1: triphenyl(propan-2-yl)phosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: ortho-bromobenzaldehyde In tetrahydrofuran; hexane at 0℃; for 2h; | |
88% | Stage #1: triphenyl(propan-2-yl)phosphonium iodide With n-butyllithium In tetrahydrofuran; hexane; cyclohexane at 0℃; for 0.5h; Inert atmosphere; Stage #2: ortho-bromobenzaldehyde In tetrahydrofuran; hexane; cyclohexane at 0 - 20℃; for 3.5h; Inert atmosphere; |
75% | Stage #1: triphenyl(propan-2-yl)phosphonium iodide With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.5h; Sealed tube; Stage #2: ortho-bromobenzaldehyde In tetrahydrofuran at 20℃; | |
Stage #1: triphenyl(propan-2-yl)phosphonium iodide With potassium-t-butoxide In tetrahydrofuran at 20℃; Stage #2: ortho-bromobenzaldehyde In tetrahydrofuran Reflux; | ||
Stage #1: triphenyl(propan-2-yl)phosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: ortho-bromobenzaldehyde In tetrahydrofuran; hexane for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With n-butyllithium; In tetrahydrofuran; hexane; | Example 1c Preparation of ethyl 2- (4-chlorophenyl) -3-methylbut-2-enoate) A solution of n-butyl lithium in hexane (20 ml, 0.03 mol) was added dropwise to a stirred solution of ethyl 4-chlorophenylglyoxylate (6.4 g, 0.03 mol) prepared in Example 1b, at -10 C. under nitrogen, during which time an exothermic reaction occurred and a red-brown suspension was formed. A solution of iso-propyltriphenylphosphonium iodide (13.0 g, 0.03 mol) in tetrahydrofuran (10 ml) was then added dropwise to the stirred mixture at -10 C. over 10 minutes. An exothermic reaction occurred and the solution became colourless. Stirring was continued for a further 15 minutes at -10 C. after the addition was complete, and the mixture was then allowed to warm to room temperature and stirred for a further 4 hours at this temperature. The reaction mixture was poured onto ice and extracted with isopropyl ether. The organic solution was evaporated in vacuo. The residue was stirred with isopropyl ether and the precipitate was filtered off. The solution was evaporated in vacuo and the product purified by flash silica column chromatography, eluding with petroleum ether/acetone (9:1) to give the title compound as a yellow oil (4.0 g, 56%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexanes at 0℃; for 1h; Stage #2: (S)-5-Oxopyrrolidine-3-carbaldehyde In tetrahydrofuran; hexanes at 0 - 20℃; for 3h; | 2.3 n-BuLi 2.5 M in hexanes (2.5 mL, 6.2 mmol) was added to a stirred ice-cooled solution of triphenylphosphonium iodide (1.9 g, 4.5 mmol) in anhydrous THF (60 mL) under nitrogen atmosphere. The mixture was stirred at 0°C for 1 h. Then a solution of (S)-5-Oxopyrrolidine-3-carbaldehyde (III) (200 mg, 1.8 mmol) in THF (10+5 mL) was added via canula, and the mixture was allowed to arrive to room temperature and stirred for 3 h. The solvent was evaporated under pressure and the residue was poured into EtOAc (25 mL) and was successively washed with saturated aqueous NaHCO3. The organic phase was dried over MgSO4 and solvent was removed. The residue (320 mg) was chromatographed on Baker silica gel using EtOAc as eluent to afford pure (R)-4-(2-Methylprop-1-enyl)pyrrolidin-2-one (IV) (100 mg, 41% yield). Characterization of (IV) (R=H): 1H-NMR (250 MHz, CDCl3) 1.7 (d, 4JH-H = 1.25 Hz, 3H), 1.8 (d, 4JH-H = 1. 25 Hz, 3H), 2.1 (dd, 3JH-H =8.75 Hz, 2JH-H = 17 Hz, 2H), 2.5 (dd, 3JH-H =8.75 Hz, 2JH-H =16.5 Hz, 1H), 3.0 (dd, 3JH-H = 7 Hz, 2JH-H = 9 Hz, 1H), 3.3 (sept, JH-H = 9 Hz, 1H), 3.5 (t, JH-H = 7.5 Hz, 1H), 5.1 (d, 3JH-H = 7.5 Hz, 1H), 6.1 (broad singlet, 1H).13C-NMR (62.5 MHz, CDCl3) 18.0 (1C), 25.5 (1C), 34.2 (1C), 37.2 (1C), 48.3 (1C), 125.5 (1C), 131.4 (1C), 178.3 (1C).appearance: colourless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: o-(phenylethynyl)benzaldehyde In tetrahydrofuran at 0 - 20℃; for 16h; Inert atmosphere; | |
67% | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: o-(phenylethynyl)benzaldehyde In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere; | |
24% | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran at 0℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: o-(phenylethynyl)benzaldehyde In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Schlenk technique; |
With n-butyllithium In tetrahydrofuran at 0 - 20℃; | ||
Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; Stage #2: o-(phenylethynyl)benzaldehyde In tetrahydrofuran; hexane at 0 - 20℃; | ||
Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Inert atmosphere; Stage #2: o-(phenylethynyl)benzaldehyde In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere; Stage #2: Methyl 4-benzoylbutanoate In tetrahydrofuran; hexane at -30 - -25℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; cyclohexane at -78 - 0℃; for 0.5h; Inert atmosphere; Stage #2: ethyl 3-phenyl-2-propenoate In tetrahydrofuran at -78 - 25℃; Inert atmosphere; | B General Procedure B: Cyclopropanation of α,β-unsaturated esters; To a suspension of the alkylphosphonium iodide (1.0 equiv.) in anhydrous THF (0.3 M) at -78°C was added n-BuLi (2.0 M In cyclohexane, 1.0 equiv.) under an argon atmosphere. The resulting mixture was warmed to 0°C and stirred for 30 min. The reaction mixture was cooled to -78'C followed by the addition of a solution of the α,β-unsaturated ester (1.0 equiv.) in anhydrous THF (0.5 M). The reaction mixture was stirred for 2 h at 0°C, then slowly warmed to 25'C, and stirred overnight. The solution was poured onto 1 HCI. The aqueous layer was extracted with EtOAc. The combined organic layers were sequentially washed with saturated NaHC03> brine, dried over NazS04, and concentrated in vacuo. The crude cyclopropane was purified by flash chromatography (Si02, cyclohexane/ChfeCb) to furnish the pure cyclopropyl ester.; Ethyl 2^-dimethyl-.^iis^-phenylcvclopropariecarboxylate; Isopropyitriphenylphosphonium iodide (21.6 g, 50 mmol) and ethyl cinnamate (8.81 g, 50 mmol) were reacted as described under General Procedure B to furnish the title compound (6.58 g, 60%) as a colorless oil. 1H NMR (300 MHz, CDCb) δ 7.31-7.15 (m, 5H), 4.18 (q, J - 7.3 Hz, 2H), 2.70 (d, J = 5.6 Hz, 1H), 1.96 (d, J = 5.6 Hz, 1H), 1.38 (s, 3H), 1.31 (t, J • 7.3 Hz, 3H), 0.93 (s. 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: isopropyltriphenylphosphonium iodide With sodium amide In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; Stage #2: myrtenal In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; | |
82% | Stage #1: isopropyltriphenylphosphonium iodide With sodium amide In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Stage #2: myrtenal In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; | |
With sodium amide In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; cyclohexane at -78 - 0℃; for 0.5h; Inert atmosphere; Stage #2: ethyl 3-phenyl-2-propenoate In tetrahydrofuran; cyclohexane at -78 - 20℃; Inert atmosphere; | G Cyclopropanatlon of α,β-unsaturated esters General procedure: To a suspension of the alkylphosphonium halide (1.2 equiv.) in anhydrous THF (0.3 M) at -78°C was added /7-BuLi (2.0 M in cyclohexane, 1.1 equiv ) under an argo atmosphere. The resulting mixture was warmed to 0*C and stirred for 30 min. The reaction mixture was cooled to -78"C followed by the addition of a solution of the α,β-unsaturated ester (1.0 equiv.) in anhydrous THF (0.5 ). The reaction mixture was stirred for 2 h at OX, then slowly warmed to ambient temperature and stirred overnight. The solution was poured onto 1N HCI. The aqueous layer was extracted with ethyl acetate and the combined organic layers were sequentially washed with saturated NaHC03, brine, dried over a2S04, and concentrated in vacuo. The crude cyclopropane was purified by column chromatography (Si02, cyclohexane/CH2CI2) to furnish the pure cyclopropyl ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere; Stage #2: 3-phenylisoxazole-5-carbaldehyde In tetrahydrofuran; hexane for 5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Stage #1: triphenyl(propan-2-yl)phosphonium iodide With potassium-t-butoxide In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: o-carboxybenzaldehyde In tetrahydrofuran for 21h; Heating; Inert atmosphere; | Procedure for C2-C3 benzo-fused morphamide S20 Isopropyl(triphenyl)phosphonium iodide (3.46 g, 8.00 mmol) was dissolved in 15 mL dry THF in a dry flaskunder nitrogen then cooled to 0 °C (ice/water). Potassium tert-butoxide (1.0 M in THF; 12 mL, 12.0 mmol) was addedvia syringe dropwise down the side of the vial over the course of 90 s, quickly turning the mixture bright red. The icebath was removed and the mixture was stirred at room temp for 30 min. 2-Formylbenzoic acid (S19; 600 mg, 4.00mmol) was added in one portion, then the flask was fitted with a reflux condenser. The mixture was heated to 70 °Cfor 21 hrs under a balloon of Ar. Upon cooling to room temp, the reaction was quenched by pouring into 20 mL sat.NH4Cl, then diluting with 20 mL ethyl acetate. The phases were separated, and the organic phase was extracted withsix 20 mL portions of 2 M NaOH. The combined aqueous phases were acidified to pH ~1 with concentrated HCl, thenextracted with six 40 mL portions of ethyl acetate. The combined organics were dried over anhydrous sodium sulfate,filtered to remove solids, and concentrated in vacuo. The crude residue was purified via flash chromatography oversilica (4 to 20% ethyl acetate:hexanes, increasing in 4% increments; loaded residue with PhMe). Obtained 655 mg ofa white solid (93.0% yield).69 |
92% | Stage #1: triphenyl(propan-2-yl)phosphonium iodide With potassium-t-butoxide In tetrahydrofuran at 20℃; for 1.5h; Stage #2: o-carboxybenzaldehyde In tetrahydrofuran Reflux; | |
Stage #1: triphenyl(propan-2-yl)phosphonium iodide With potassium-t-butoxide In tetrahydrofuran at 20℃; for 1.5h; Stage #2: o-carboxybenzaldehyde In tetrahydrofuran Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 6-chlorohexanal In tetrahydrofuran at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: 3-methyl-4-anisaldehyde In tetrahydrofuran at 40℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2h; Stage #2: 2-bromophenylacetaldehyde In tetrahydrofuran; hexane at 20℃; | |
Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2h; Inert atmosphere; Stage #2: 2-bromophenylacetaldehyde In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2h; Stage #2: (2-methoxy-phenyl)-acetaldehyde In tetrahydrofuran; hexane at 20℃; | |
Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2h; Inert atmosphere; Stage #2: (2-methoxy-phenyl)-acetaldehyde In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2h; Stage #2: 4-fluorophenylacetaldehyde In tetrahydrofuran; hexane at 20℃; | |
Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2h; Inert atmosphere; Stage #2: 4-fluorophenylacetaldehyde In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2h; Stage #2: 4-methylphenylacetaldehyde In tetrahydrofuran; hexane at 20℃; | |
Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2h; Inert atmosphere; Stage #2: 4-methylphenylacetaldehyde In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2h; Stage #2: 4-Methoxyphenylacetaldehyde In tetrahydrofuran; hexane at 20℃; | |
Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2h; Inert atmosphere; Stage #2: 4-Methoxyphenylacetaldehyde In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With potassium <i>tert</i>-butylate In dimethyl sulfoxide Schlenk technique; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667h; Stage #2: 2-methoxy-6-nitrobenzaldehyde In tetrahydrofuran at -78 - 0℃; | 1 1-Methoxy-2-(2-methyl-propenyl)-3-nitro-benzene (3.5): (2- Propyl)triphenylphosphonium iodide (1.55 g, 3.59 mmol) was dissolved in dry THF (20 mL), then it was cooled to -78 °C under N2 and n-BuLi (1.5 mL, 3.82 mmol, 2.5 mol/L in THF) was added dropwise to the reaction system in 10 min. Then the temperature was allowed to reach 0 °C slowly. Then it was cooled to -78 °C again, 2-methoxy-6-nitro-benzaldehyde (3.4) (0.49 g,2.7 mmol) in THF was added dropwise in 30 min. After the addition, the reaction was monitored by TLC. Then it was quenched with water (20 mL), extracted with EtOAc (3x30 mL). The organic phase was combined, dried over anhydrous sodium sulfate, then concentrated and purified on silica gel column chromatography using EtOAc/Petroether (v/v 1 :5) as eluent to provide l-methoxy-2-(2-methyl-propenyl)-3-nitro-benzene (3.5) (400 mg, 70% yield) as a yellow oil. [MS m/z: 208 (M+l)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: triphenyl(propan-2-yl)phosphonium iodide With potassium-t-butoxide In tetrahydrofuran at 20℃; for 1.5h; Stage #2: 4-bromo-2-formylbenzoic acid In tetrahydrofuran Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | Stage #1: triphenyl(propan-2-yl)phosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Inert atmosphere; Stage #2: 1-tert-butyl 2-methyl (2S)2,5-dihydro-1H-pyrrole-1,2-dicarboxylate In tetrahydrofuran; hexane at 20℃; | 5 Preparation of Compound V Under nitrogen atmosphere, n-butyllithium (2.5M solution in hexane, 880 mL) was added dropwise to a solution (3 L) of isopropyltriphenylphosphonium iodide (864 g) in tetrahydrofuran. The reaction was stirred at 0°C for 30 minutes, then a solution of compound IV (455 g) in tetrahydrofuran (1 L) was added dropwise. After the dropwise addition, the mixture was stirred at room temperature until Compound IV disappeared (TLC), quenched by adding 10% dilute hydrochloric acid, extracted and separated, the aqueous phase was extracted once with ethyl acetate (2 L), and the combined organic phases were dried over anhydrous magnesium sulfate, Dry under reduced pressure. The obtained crude product was stirred with methyl tertiary ether (2 L), the solid was removed by suction filtration, and the filtrate was concentrated to dryness under reduced pressure to obtain 496 g of compound V with a yield of 92%. |
Tags: 24470-78-8 synthesis path| 24470-78-8 SDS| 24470-78-8 COA| 24470-78-8 purity| 24470-78-8 application| 24470-78-8 NMR| 24470-78-8 COA| 24470-78-8 structure
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Code | Phrase |
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Prevention | |
Code | Phrase |
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P220 | Keep/Store away from clothing/combustible materials. |
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P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
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Response | |
Code | Phrase |
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P304 | IF INHALED: |
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P306 | IF ON CLOTHING: |
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P321 | |
P322 | |
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P337 | If eye irritation persists: |
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P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
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P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
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P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
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P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
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P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
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Disposal | |
Code | Phrase |
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P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
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 |
Sorry,this product has been discontinued.
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