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CAS No. : | 66990-30-5 | MDL No. : | MFCD00041683 |
Formula : | C23H38O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DIEDVCMBPCRJFQ-UHFFFAOYSA-N |
M.W : | 346.55 | Pubchem ID : | 538457 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | N/A |
Hazard Statements: | H315-H319 | 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 |
---|---|---|
(i) aq. NH2OH*HCl, CuCl2, EtNH2, KOH, (ii) /BRN= 1758339/, MeOH; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With potassium hydroxide; methylamine; copper(l) chloride In tetrahydrofuran; methanol; water 1) 20 deg C, 4 h, 2) 40 deg C, 1 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With oxalyl dichloride In dichloromethane at 20℃; for 3h; | |
With thionyl chloride; N,N-dimethyl-formamide In pentane Heating; | ||
With thionyl chloride In tetrahydrofuran Heating; |
With oxalyl dichloride In dichloromethane at 20℃; | ||
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide 2.) CH2Cl2, RT, 14 h; Multistep reaction. Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanol; dmap; trimethylsilyl bromide; water; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanol; dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide 2.) CH2Cl2, RT, 14 h; Multistep reaction. Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; Darkness; | |
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49.7% | With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With sulfuric acid for 5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70.4% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
UV-irradiation; circularly polarized light; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: oxalyl chloride / CH2Cl2 / 20 °C 2: 11 percent / pyridine / CH2Cl2 / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: oxalyl chloride / CH2Cl2 / 20 °C 2: 56 percent / pyridine / CH2Cl2 / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: oxalyl chloride / CH2Cl2 / 20 °C 2: 4 percent / pyridine / CH2Cl2 / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 81 percent / H2SO4 / 5 h / Heating 2: 59 percent / methanol / 20 h / 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride / CH2Cl2 2: hydrazine hydrate / CH2Cl2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) aq. p-TsOH, MeOH, 2.) DMAP, DCC, 3.) TMSBr, 4.) H2O 2: pyridine / various solvent(s) / 20 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: SOCl2, DMF / pentane / Heating 2: benzene / 1) 20 deg C, 3 h, 2) 60 deg C, 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.50 g (41%) | With pyridine In tetrahydrofuran | 11 Tetraethylene glycol mono- 10,12-tricosadiynoate EXAMPLE 11 Tetraethylene glycol mono- 10,12-tricosadiynoate 10,12-Tricosadiynoic acid (2.50 g, 0.007 mol) in tetrahydrofuran (30 ml) was reacted with oxalyl chloride (2.25 g, 0.017 mol) to obtain the corresponding acid chloride. This acid chloride (2.45 g, 0.007 mol) dissolved in anhydrous tetrahydrofuran (10 ml) was added dropwise to a mixture of tetraethylene glycol (1.32 g, 0.007 mol) and anhydrous pyridine (0.83 g, 0.01 mol) in anhydrous tetrahydrofuran (40 ml). The mixture was stirred overnight at room temperature. The precipitated pyridinium salt was filtered off and the solvent removed under vacuum. The resulting liquid was purified by flash chromatography (silica gel/ethyl acetate) to give 1.50 g (41%) of the title compound as a colour less oil. 1 H NMR (60 MHz, CDCl3): δ 0.88 (m, 3H, CH3 CH2), 1.30 (m, 28H, CH2), 2.20 (m, 6H, CH2), 3.65 (s, 11H, 7*CH2 O), 4.20 (m, 2H, CH2 CO). |
1.50 g (41%) | With pyridine In tetrahydrofuran | 11 Tetraethylene glycol mono-10,12-tricosadiynoate EXAMPLE 11 Tetraethylene glycol mono-10,12-tricosadiynoate 10,12-Tricosadiynoic acid (2.50 g, 0.007 mol) in tetrahydrofuran (30 ml) was reacted with oxalyl chloride (2.25 g, 0.017 mol) to obtain the corresponding acid chloride. This acid chloride (2.45 g, 0.007 mol) dissolved in anhydrous tetrahydrofuran (10 ml) was added dropwise to a mixture of tetraethylene glycol (1.32 g, 0.007 mol) and anhydrous pyridine (0.83 g, 0.01 mol) in anhydrous tetrahydrofuran (40 ml). The mixture was stirred overnight at room temperature. The precipitated pyridinium salt was filtered off and the solvent removed under vacuum. The resulting liquid was purified by flash chromatography (silica gel/ethyl acetate) to give 1.50 g (41%) of the title compound as a colourless oil. 1 H NMR (60 MHz, CDCl3): δ0.88 (m, 3H, CH3 CH2), 1.30 (m, 28H, CH2), 2.20 (m, 6H, CH2), 3.65 (s, 14H, 7*CH2 O), 4.20 (m, 2H, CH2 CO). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.68 g (74%) | With sulfuric acid In methanol | 13.a a a Methyl 10,12-tricosadiynoate 10,12- Tricosadiynoic acid (3.0 g, 0.0084 mol), methanol (15 ml) and concentrated sulfuric acid (0.8 ml) were heated to reflux and stirred for 1 hour. The cooled mixture was taken up in either (40 ml) and washed with 10% NaHCO3 (20 ml) and water (20 ml), and the organic phase was dried (MgSO4). Evaporation of the solvent gave 2.68 g (74%) of the title compound. 1 H NMR (60 MHz, CDCl3): δ 0.98 (m, 3H, CH3 CH2), 1.28 (m, 28H, CH2), 2.25 (m, 6H, CH2), 3.70 (s, 3H, CH2 O). |
2.68 g (74%) | With sulfuric acid In methanol | 13.a a a Methyl 10,12-tricosadiynoate 10,12-Tricosadiynoic acid (3.0 g, 0.0084 mol), methanol (15 ml) and concentrated sulfuric acid (0.8 ml) were heated to reflux and stirred for 1 hour. The cooled mixture was taken up in ether (40 ml) and washed with 10% NaHCO3 (20 ml) and water (20 ml), and the organic phase was dried (MgSO4). Evaporation of the solvent gave 2.68 g (74%) of the title compound. 1 H NMR (60 MHz, CDCl3): δ0.98 (m, 3H, CH3 CH2), 1.28 (m, 28H, CH2), 2.25 (m, 6H, CH2), 3.70 (s, 3H, CH3 O). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2 (2) (2) Tricosa-10,12-diynoic acid 10-Undecynoic acid (21.8 g, 0.120 mol) was neutralized with a solution of 57 mL 10 percent KOH in water and hydroxylamine hydrochloride (0.380 g) was added. Then a catalyst consisting of a solution of 1.9 g cuprous chloride in 16 g 70 percent aqueous ethylamine was added. A yellow precipitate formed immediately. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
UV-irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
UV-irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
for 0.166667h; UV-irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In various solvent(s) at 10℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57.8% | Stage #1: tricosa-10,12-diynoic acid With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1h; Inert atmosphere; Cooling with ice; Stage #2: hexa-tert-butyl 10,10'-(6-((2-aminoethyl)amino)-1,3,5-triazine-2,4-diyl)bis(1,4,7,10-tetraazacyclo-dodecane-1,4,7-tricarboxylate) In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Cooling with ice; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38.9% | Stage #1: Fmoc-Lys(tert-butoxycarbonyl) In dichloromethane; N,N-dimethyl-formamide at 45 - 55℃; for 0.333333h; Microwave irradiation; solid phase reaction; Stage #2: With piperidine In dichloromethane; N,N-dimethyl-formamide at 45 - 55℃; for 0.0833333h; Microwave irradiation; solid phase reaction; Stage #3: tricosa-10,12-diynoic acid; N-α-Fmoc-(4-morpholine-1,8-naphthalimido)-Lysine Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58.2% | Stage #1: Nα-(Fluoren-9-ylmethoxycarbonyl)-N(im)-(tert-butyloxycarbonyl)-L-histidine In dichloromethane; N,N-dimethyl-formamide at 45 - 55℃; for 0.333333h; Microwave irradiation; solid phase reaction; Stage #2: With piperidine In dichloromethane; N,N-dimethyl-formamide at 45 - 55℃; for 0.0833333h; Microwave irradiation; solid phase reaction; Stage #3: tricosa-10,12-diynoic acid Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: thionyl chloride / dichloromethane / 16 h / 20 - 25 °C / Inert atmosphere 1.2: 24.5 h / 20 °C / Inert atmosphere 2.1: N,N-dimethyl-formamide / 1 h / 50 °C / Inert atmosphere 2.2: 6 h / 50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | Stage #1: tricosa-10,12-diynoic acid With thionyl chloride In dichloromethane at 20 - 25℃; for 16h; Inert atmosphere; Stage #2: ethylenediamine In dichloromethane at 20℃; for 24.5h; Inert atmosphere; | |
Stage #1: tricosa-10,12-diynoic acid With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h; Stage #2: ethylenediamine In dichloromethane for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 96h; Inert atmosphere; Darkness; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h 2: pyridine / dichloromethane / 5 h / 0 - 20 °C / Darkness; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diphenyl phosphoryl azide; triethylamine In tetrahydrofuran at 60℃; for 2h; Darkness; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: diphenyl phosphoryl azide; triethylamine / tetrahydrofuran / 2 h / 60 °C / Darkness 2: tetrahydrofuran / 6 h / 20 °C / Darkness |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.56 g | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: oxalyl dichloride / dichloromethane / 3 h / 20 °C 2: triethylamine / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: oxalyl dichloride / dichloromethane / 3 h / 20 °C 2: triethylamine / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: oxalyl dichloride / dichloromethane / 3 h / 20 °C 2: triethylamine / dichloromethane; tetrahydrofuran / 18 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere; Darkness 2: dichloromethane / 24 h / 20 °C 3: potassium carbonate / acetonitrile / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere; Darkness 2: dichloromethane / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere; Darkness 2: triethylamine / dichloromethane / 24 h / 20 °C / Inert atmosphere; Darkness |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere; Darkness 2: triethylamine / dichloromethane / 24 h / 20 °C / Inert atmosphere; Darkness |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: oxalyl dichloride / dichloromethane / 3 h / 20 °C 2: triethylamine / dichloromethane / 6 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: tricosa-10,12-diynoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; Inert atmosphere; Stage #2: With ammonium hydroxide In tetrahydrofuran Inert atmosphere; Cooling with ice; Stage #3: With lithium aluminium tetrahydride In diethyl ether Inert atmosphere; Cooling with ice; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With copper(l) iodide; hydroxylamine hydrochloride; ethylamine; potassium hydroxide In tetrahydrofuran; methanol; water at 0 - 20℃; for 24h; |