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CAS No. : | 111-12-6 | MDL No. : | MFCD00009530 |
Formula : | C9H14O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FRLZQXRXIKQFNS-UHFFFAOYSA-N |
M.W : | 154.21 | Pubchem ID : | 8092 |
Synonyms : |
|
Chemical Name : | Methyl oct-2-ynoate |
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.67 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 44.82 |
TPSA : | 26.3 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.0 cm/s |
Log Po/w (iLOGP) : | 2.56 |
Log Po/w (XLOGP3) : | 3.16 |
Log Po/w (WLOGP) : | 1.82 |
Log Po/w (MLOGP) : | 2.17 |
Log Po/w (SILICOS-IT) : | 2.02 |
Consensus Log Po/w : | 2.35 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.52 |
Solubility : | 0.463 mg/ml ; 0.003 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.38 |
Solubility : | 0.0639 mg/ml ; 0.000414 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.03 |
Solubility : | 1.44 mg/ml ; 0.00933 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.68 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280 | UN#: | N/A |
Hazard Statements: | H302-H315 | 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 |
---|---|---|
With sulfuric acid | ||
8.9 g | With hydrogenchloride | [11,11-2H2]18:2n - 6 2-Octynoic acid (9.2 g; Sigma-Aldrich) was refluxed for 1 h with 200 ml of methanol containing 2 ml conc. hydrochloric acid. The resulting methyl ester (8.9 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 7% 2: 12% | With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; methyllithium; diisobutylaluminium hydride In tetrahydrofuran; hexane at -50℃; for 1h; | |
With quinoline; hydrogen In ethyl acetate Yield given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With lithium aluminium tetrahydride; In tetrahydrofuran; at -5℃; for 3h; | A suspension of LiAlH4 (3.00 g, 78.70 mmol) in anhydrous THF (40 mL) was cooled to -5C, stirred,treated with a solution of 2 (10.03 g, 65.00 mmol) in anhydrous THF (5 mL), stirred at -5C for 3 h, decomposed by cold H2O(100 mL), acidified by H2SO4 solution (1 M) to pH 2-3, and extracted by Et2O (3 50 mL). The extract was washed withsaturated NaCl solution. The combined organic fraction was dried over Na2SO4 and decanted. The solvent was removedin vacuo. The residue was chromatographed over a column of silica gel using a gradient of Et2O-petroleum ether (1:3, 1:2, 1:1).The yield of 3 was 6.25 g (76%), Rf 0.37 (Et2O-hexane, 1:1). 1 NMR spectrum (300 MHz, CDCl3, , ppm, J/Hz): 4.25 (2H,m, H-1), 2.25 (2H, t, J = 6.8, H-4), 1.55 (2H, m, H-5), 1.2-1.4 (4H, m, H-6, 7), 0.87 (1H, t, J = 7, H-8). 13C NMR spectrum(75 MHz, CDCl3, , ppm): 87.13 (s, -3), 78.52 (s, -2), 51.01 (s, -1), 31.29 (s, -6), 28.11 (s, -5), 21.78 (s, -7), 19.15(s, -4), 14.11 (s, -8). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7.8 g | With lithium aluminium deuteride; In diethyl ether; at 0℃; for 1h; | methyl ester (8.9 g) was dissolved in 30 ml of diethyl ether and slowly added at 0 C under magnetic stirring to a suspension of 1.8 g LiAlD4 in 50 ml of diethyl ether. After stirring at 0 C for 1 h, the reaction was quenched by slow addition of tetrahydrofuran/water and the alcohol (7.8 g) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | Stage #1: methyl 2-octynoate; benzyl ethyl malonate With sodium hydroxide In 1,4-dioxane at 20℃; for 4h; Stage #2: formaldehyd In 1,4-dioxane at 20℃; for 1h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With oxygen; copper(ll) bromide; palladium dichloride In water; toluene at 60℃; for 16h; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With copper(ll) bromide; palladium dichloride; In tetrahydrofuran; at 25℃; for 12h; | General procedure: Palladium chloride (9 mg, 0.05 mmol), CuBr2 (221mg, 1 equiv.) were mixed with THF(2.0 mL)in a test tube (10 mL) equipped with a magnetic stirring bar. Then, alkyne (1.0 mmol) and allylic alcohol (1.0 mmol)were added. The mixture was stirred at room temperature for 12 h. The reactionmixture was taken up by in ether (10 mL) and washed with brine (10mL). The organic layer was dried (MgSO4), concentrated in vacuo andpurified by flash silica gel chromatography using petroleum ether/ethyl acetate100:1 to give the desired products. The stereochemistry of 3ma and 3aa was further confirmed by NOESY methods. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With copper(II) choride dihydrate; palladium dichloride; In tetrahydrofuran; at 25℃; for 12h; | General procedure: Palladium chloride (9 mg, 0.05 mmol), CuBr2 (221mg, 1 equiv.) were mixed with THF(2.0 mL)in a test tube (10 mL) equipped with a magnetic stirring bar. Then, alkyne (1.0 mmol) and allylic alcohol (1.0 mmol)were added. The mixture was stirred at room temperature for 12 h. The reactionmixture was taken up by in ether (10 mL) and washed with brine (10mL). The organic layer was dried (MgSO4), concentrated in vacuo andpurified by flash silica gel chromatography using petroleum ether/ethyl acetate100:1 to give the desired products. The stereochemistry of 3ma and 3aa was further confirmed by NOESY methods. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With copper(ll) bromide; palladium dichloride; In tetrahydrofuran; at 25℃; for 12h; | General procedure: Palladium chloride (9 mg, 0.05 mmol), CuBr2 (221mg, 1 equiv.) were mixed with THF(2.0 mL)in a test tube (10 mL) equipped with a magnetic stirring bar. Then, alkyne (1.0 mmol) and allylic alcohol (1.0 mmol)were added. The mixture was stirred at room temperature for 12 h. The reactionmixture was taken up by in ether (10 mL) and washed with brine (10mL). The organic layer was dried (MgSO4), concentrated in vacuo andpurified by flash silica gel chromatography using petroleum ether/ethyl acetate100:1 to give the desired products. The stereochemistry of 3ma and 3aa was further confirmed by NOESY methods. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With copper(ll) bromide; palladium dichloride; In tetrahydrofuran; at 25℃; for 12h; | General procedure: Palladium chloride (9 mg, 0.05 mmol), CuBr2 (221mg, 1 equiv.) were mixed with THF(2.0 mL)in a test tube (10 mL) equipped with a magnetic stirring bar. Then, alkyne (1.0 mmol) and allylic alcohol (1.0 mmol)were added. The mixture was stirred at room temperature for 12 h. The reactionmixture was taken up by in ether (10 mL) and washed with brine (10mL). The organic layer was dried (MgSO4), concentrated in vacuo andpurified by flash silica gel chromatography using petroleum ether/ethyl acetate100:1 to give the desired products. The stereochemistry of 3ma and 3aa was further confirmed by NOESY methods. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With copper(ll) bromide; palladium dichloride; In tetrahydrofuran; at 25℃; for 12h; | General procedure: Palladium chloride (9 mg, 0.05 mmol), CuBr2 (221mg, 1 equiv.) were mixed with THF(2.0 mL)in a test tube (10 mL) equipped with a magnetic stirring bar. Then, alkyne (1.0 mmol) and allylic alcohol (1.0 mmol)were added. The mixture was stirred at room temperature for 12 h. The reactionmixture was taken up by in ether (10 mL) and washed with brine (10mL). The organic layer was dried (MgSO4), concentrated in vacuo andpurified by flash silica gel chromatography using petroleum ether/ethyl acetate100:1 to give the desired products. The stereochemistry of 3ma and 3aa was further confirmed by NOESY methods. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With copper(ll) bromide; palladium dichloride; In tetrahydrofuran; at 25℃; for 12h; | General procedure: Palladium chloride (9 mg, 0.05 mmol), CuBr2 (221mg, 1 equiv.) were mixed with THF(2.0 mL)in a test tube (10 mL) equipped with a magnetic stirring bar. Then, alkyne (1.0 mmol) and allylic alcohol (1.0 mmol)were added. The mixture was stirred at room temperature for 12 h. The reactionmixture was taken up by in ether (10 mL) and washed with brine (10mL). The organic layer was dried (MgSO4), concentrated in vacuo andpurified by flash silica gel chromatography using petroleum ether/ethyl acetate100:1 to give the desired products. The stereochemistry of 3ma and 3aa was further confirmed by NOESY methods. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In benzene; for 2h;Reflux; Inert atmosphere; | General procedure: Representative procedure for the [222] cycloaddition of diyne 1a with alkynyl ester 4.Aflask was charged with [Ir(cod)Cl]2(7.0 mg, 0.01 mmol) and rac-BINAP (12.2 mg, 0.02 mmol). The flask was evacuated and filled with argon. To the flask were added benzene (5 mL) and methyl 2-undecynoate (4c) (444 mg, 2.3 mmol). Diyne1a(234 mg, 1.0 mmol) was added to the reaction mixture. The mixture was stirred under reflux for 2 h. The progress of the reaction was monitored by GLC. After the reaction was complete, the solvent was evaporated invacuo. Column chromatography of the residue gave 5ac(n-hexane/AcOEt 85:15, 378 mg, 0.87 mmol, 88% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 16h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 16h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 16h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With CoH(P(CH3)3)4; In toluene; at 160℃; for 0.5h;Glovebox; Inert atmosphere; Sealed tube; | General procedure: In a glove box, a microwave reaction vial (0.5-2 mL) was charged with HCo(PMe3)4 (18.2 mg, 0.05 mmol, 5 mol%) and then sealed. Next, a degassed mixture of the corresponding alkyne (1.00 mmol, 1 equiv) and pinacolborane (97%, 157 muL 1.05 mmol, 1.05 equiv) in toluene (1mL) was added via syringe. The reaction mixture was heated in an oilbath at 160 C for 30 min. The mixture was diluted with petroleum ether (2 mL), filtered through a plug of silica gel, and washed with Et2O (3 × 10 mL). The crude product was purified by silica gel chromatography (mixtures of pentane/Et2O as eluents) to afford the final products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With N-iodo-succinimide; acetic acid; lithium chloride; In dichloromethane; at 20℃; for 48h; | General procedure: A 10 mL glass vial with a screw cap was charged with alkynes (0.2 mmol), NIS (0.3 mmol, 1.5equiv.), LiCl (0.4 mmol, 2 equiv) and a solvent mixture of DCM (0.5 mL) and HOAc (0.5 mL).The reaction mixture was stirred at -25 oC for 24 h. Upon completion, the reaction mixture was quenched with saturated NaCl solution and was extracted with EtOAc, the combined organic layers were dried with anhydrous Na2SO4 and the solvent was removed in vacuum. The residue was purified by flash column chromatography on silica gel (eluted with hexanes and ethyl acetate)to give the desired products. |
Tags: 111-12-6 synthesis path| 111-12-6 SDS| 111-12-6 COA| 111-12-6 purity| 111-12-6 application| 111-12-6 NMR| 111-12-6 COA| 111-12-6 structure
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