ISO product Name Methoprene Synonyms S-Methoprene Molecular Formula C19H34O3 Molecular Weight 310.4715 InChI InChI=1/C19H34O3/c1-15(2)22-1
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inquirySynonyms: ALTOSID(R);11-METHOXY-3,7,11-TRIMETHYL-2E,4E-DODECADIENOIC ACID, ISOPROPYL ESTER;METHOPRENE (TM);METHOPRENE;ISOPROPYL (2E,4E)-11-METHOXY-3,7,11-TRIMETHYL-2,4-DODECADIENOATE;PRECOR;ZR-515;2,4-dodecadienoicacid,11-methoxy-3,7,11-trimethyl-,
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5-(6'-methoxy-2',6'-dimethylheptyl)-3-methyl-2,5-dihydrothiophene-2-carboxylic acid
A
Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate
B
methoprene
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | A n/a B n/a C 20% |
5-(6-Methoxy-2,6-dimethyl-heptyl)-3-methyl-2,5-dihydro-thiophene-2-carboxylic acid isopropyl ester
A
Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate
B
methoprene
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | A n/a B n/a C 20% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 12h; Product distribution; | A n/a B n/a C 90 mg |
A
Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate
B
methoprene
C
isopropyl 3,7,11-trimethyl-2ξ,4E,10-dodecatrienoate
Conditions | Yield |
---|---|
With lithium carbonate; lithium bromide In N,N-dimethyl-formamide for 1h; Heating; Yield given. Title compound not separated from byproducts; | A n/a B 0.18 g C 10% |
With lithium carbonate; lithium bromide In N,N-dimethyl-formamide for 1h; Heating; Yields of byproduct given; | A n/a B 0.18 g C 10% |
Conditions | Yield |
---|---|
(i) SOCl2, (ii) /BRN= 635639/; Multistep reaction; |
7-methoxy-3,7-dimethyloctanal
diisopropyl ester of 2-methyl-3-isopropoxycarbonyl-2-propenylphosphonic acid
A
Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate
B
methoprene
Conditions | Yield |
---|---|
With tetra(n-butyl)ammonium hydroxide In benzene other reagents; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
methyllithium
Isopropyl (2Z,4E)-3-Acetoxy-11-methoxy-7,11-dimethyl-2,4-dodecadienoate
methoprene
Conditions | Yield |
---|---|
With copper(l) iodide 1.) ether, -30 degC, 10 min; 2.) ether, -20 degC, 2h; Yield given. Multistep reaction; |
methyllithium
Isopropyl (4E)-3-Diethoxyphosphoryloxy-11-methoxy-7,11-dimethyl-2,4-dodecadienoate
A
Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate
B
methoprene
Conditions | Yield |
---|---|
With copper(l) iodide 1.) ether, -30 degC, 30 min; 2.) -78 degC, 1h; Yield given. Multistep reaction. Yields of byproduct given; |
2-(1-Bromo-7-methoxy-3,7-dimethyl-octyl)-3-methyl-cyclopropanecarboxylic acid isopropyl ester
methoprene
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc dibromide 1.) ether, -40 deg C to 0 deg C, 2 h, 2.) 50 deg C, 2 h; Multistep reaction; |
3-Methylthiophene
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 2: 77 percent / H2SO4 conc. / 4 h / Heating 3: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 4: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 5: diethyl ether / 0.5 h / 0 °C 6: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme | |
Multi-step reaction with 5 steps 1: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 2: 77 percent / H2SO4 conc. / 4 h / Heating 3: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 4: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 5: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme |
2-bromo-6-methylhept-5-ene
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: 68 percent / 1.) Br / 2.) THF, 2.) 25 deg C, 30 min 2: 73 percent / NaBH4 / methanol / 0.5 h / 25 °C 3: pyridine; diethyl ether / 6 h / Heating 4: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C 5: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 6: 77 percent / H2SO4 conc. / 4 h / Heating 7: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 8: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 9: diethyl ether / 0.5 h / 0 °C 10: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme | |
Multi-step reaction with 9 steps 1: 68 percent / 1.) Br / 2.) THF, 2.) 25 deg C, 30 min 2: 73 percent / NaBH4 / methanol / 0.5 h / 25 °C 3: pyridine; diethyl ether / 6 h / Heating 4: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C 5: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 6: 77 percent / H2SO4 conc. / 4 h / Heating 7: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 8: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 9: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme |
2,6-dimethyl-5-hepten-1-ol
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: pyridine; diethyl ether / 6 h / Heating 2: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C 3: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 4: 77 percent / H2SO4 conc. / 4 h / Heating 5: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 6: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 7: diethyl ether / 0.5 h / 0 °C 8: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1: pyridine; diethyl ether / 6 h / Heating 2: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C 3: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 4: 77 percent / H2SO4 conc. / 4 h / Heating 5: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 6: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 7: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme |
1-bromo-2,6-dimethylhept-5-ene
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 2: 77 percent / H2SO4 conc. / 4 h / Heating 3: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 4: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 5: diethyl ether / 0.5 h / 0 °C 6: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme | |
Multi-step reaction with 5 steps 1: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 2: 77 percent / H2SO4 conc. / 4 h / Heating 3: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 4: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 5: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme |
2,6-dimethyl-5-hepten-1-al
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 73 percent / NaBH4 / methanol / 0.5 h / 25 °C 2: pyridine; diethyl ether / 6 h / Heating 3: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C 4: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 5: 77 percent / H2SO4 conc. / 4 h / Heating 6: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 7: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 8: diethyl ether / 0.5 h / 0 °C 9: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme | |
Multi-step reaction with 8 steps 1: 73 percent / NaBH4 / methanol / 0.5 h / 25 °C 2: pyridine; diethyl ether / 6 h / Heating 3: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C 4: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 5: 77 percent / H2SO4 conc. / 4 h / Heating 6: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 7: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 8: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme |
2-(2',6'-dimethylhept-5'-enyl)-4-methylthiophene
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 77 percent / H2SO4 conc. / 4 h / Heating 2: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 3: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 4: diethyl ether / 0.5 h / 0 °C 5: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme | |
Multi-step reaction with 4 steps 1: 77 percent / H2SO4 conc. / 4 h / Heating 2: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 3: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 4: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme |
2-(6'-methoxy-2',6'-dimethylheptyl)-4-methylthiophene
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 2: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 3: diethyl ether / 0.5 h / 0 °C 4: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme | |
Multi-step reaction with 3 steps 1: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 2: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 3: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme |
5-(6'-methoxy-2',6'-dimethylheptyl)-3-methylthiophene-2-carboxylic acid
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 2: diethyl ether / 0.5 h / 0 °C 3: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 2: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme |
5-(6'-methoxy-2',6'-dimethylheptyl)-3-methyl-2,5-dihydrothiophene-2-carboxylic acid
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diethyl ether / 0.5 h / 0 °C 2: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme |
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C 2: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 3: 77 percent / H2SO4 conc. / 4 h / Heating 4: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 5: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 6: diethyl ether / 0.5 h / 0 °C 7: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme | |
Multi-step reaction with 6 steps 1: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C 2: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 3: 77 percent / H2SO4 conc. / 4 h / Heating 4: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 5: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 6: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme |
isopropyl acetoacetate
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 2: 61 percent / 4N HCl / dioxane / 0.25 h / 80 °C 3: 63 percent / p-toluenesulfonic acid / 6 h / Heating 4: 1.) copper(I) iodide / 1.) ether, -30 degC, 10 min; 2.) ether, -20 degC, 2h View Scheme | |
Multi-step reaction with 4 steps 2: 61 percent / 4N HCl / dioxane / 0.25 h / 80 °C 3: 1.) NaH / 1.) ether, 0.5h, room temp.; 2.) ether, 8h, reflux 4: 1.) copper(I) iodide / 1.) ether, -30 degC, 30 min; 2.) -78 degC, 1h View Scheme |
7-methoxy-3,7-dimethyloctanal
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: Et3N / N-(2-hydroxyethyl)-thiazolium bromide / dioxane / 20 h / 95 - 100 °C 2: sodium borohydride / tetrahydrofuran / 1 h / 0 °C 3: pyridine / 24 h / 25 °C 4: potassium t-butoxid, 18-Crown-6 / benzene / 0.5 h / Ambient temperature 5: sodium borohydride / propan-2-ol / 4 h / Heating 6: PBr3, LiBr, 2,4,6-collidine / 3 h / -40 - 0 °C 7: 1.) ZnBr, 2.) DBU / 1.) ether, -40 deg C to 0 deg C, 2 h, 2.) 50 deg C, 2 h View Scheme | |
Multi-step reaction with 4 steps 2: 61 percent / 4N HCl / dioxane / 0.25 h / 80 °C 3: 63 percent / p-toluenesulfonic acid / 6 h / Heating 4: 1.) copper(I) iodide / 1.) ether, -30 degC, 10 min; 2.) ether, -20 degC, 2h View Scheme | |
Multi-step reaction with 4 steps 2: 61 percent / 4N HCl / dioxane / 0.25 h / 80 °C 3: 1.) NaH / 1.) ether, 0.5h, room temp.; 2.) ether, 8h, reflux 4: 1.) copper(I) iodide / 1.) ether, -30 degC, 30 min; 2.) -78 degC, 1h View Scheme |
α-Keto-β-Methyl-buttersaeure-isopropylester
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: Et3N / N-(2-hydroxyethyl)-thiazolium bromide / dioxane / 20 h / 95 - 100 °C 2: sodium borohydride / tetrahydrofuran / 1 h / 0 °C 3: pyridine / 24 h / 25 °C 4: potassium t-butoxid, 18-Crown-6 / benzene / 0.5 h / Ambient temperature 5: sodium borohydride / propan-2-ol / 4 h / Heating 6: PBr3, LiBr, 2,4,6-collidine / 3 h / -40 - 0 °C 7: 1.) ZnBr, 2.) DBU / 1.) ether, -40 deg C to 0 deg C, 2 h, 2.) 50 deg C, 2 h View Scheme |
isopropyl 2-hydroxy-3-methylbutyrate
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: MnO2 2: Et3N / N-(2-hydroxyethyl)-thiazolium bromide / dioxane / 20 h / 95 - 100 °C 3: sodium borohydride / tetrahydrofuran / 1 h / 0 °C 4: pyridine / 24 h / 25 °C 5: potassium t-butoxid, 18-Crown-6 / benzene / 0.5 h / Ambient temperature 6: sodium borohydride / propan-2-ol / 4 h / Heating 7: PBr3, LiBr, 2,4,6-collidine / 3 h / -40 - 0 °C 8: 1.) ZnBr, 2.) DBU / 1.) ether, -40 deg C to 0 deg C, 2 h, 2.) 50 deg C, 2 h View Scheme |
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 63 percent / p-toluenesulfonic acid / 6 h / Heating 2: 1.) copper(I) iodide / 1.) ether, -30 degC, 10 min; 2.) ether, -20 degC, 2h View Scheme | |
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) ether, 0.5h, room temp.; 2.) ether, 8h, reflux 2: 1.) copper(I) iodide / 1.) ether, -30 degC, 30 min; 2.) -78 degC, 1h View Scheme |
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 61 percent / 4N HCl / dioxane / 0.25 h / 80 °C 2: 63 percent / p-toluenesulfonic acid / 6 h / Heating 3: 1.) copper(I) iodide / 1.) ether, -30 degC, 10 min; 2.) ether, -20 degC, 2h View Scheme | |
Multi-step reaction with 3 steps 1: 61 percent / 4N HCl / dioxane / 0.25 h / 80 °C 2: 1.) NaH / 1.) ether, 0.5h, room temp.; 2.) ether, 8h, reflux 3: 1.) copper(I) iodide / 1.) ether, -30 degC, 30 min; 2.) -78 degC, 1h View Scheme |
2-(1-Hydroxy-7-methoxy-3,7-dimethyl-octyl)-3-methyl-cyclopropanecarboxylic acid isopropyl ester
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: PBr3, LiBr, 2,4,6-collidine / 3 h / -40 - 0 °C 2: 1.) ZnBr, 2.) DBU / 1.) ether, -40 deg C to 0 deg C, 2 h, 2.) 50 deg C, 2 h View Scheme |
2-Hydroxy-11-methoxy-3,7,11-trimethyl-5-oxo-dodecanoic acid isopropyl ester
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: pyridine / 24 h / 25 °C 2: potassium t-butoxid, 18-Crown-6 / benzene / 0.5 h / Ambient temperature 3: sodium borohydride / propan-2-ol / 4 h / Heating 4: PBr3, LiBr, 2,4,6-collidine / 3 h / -40 - 0 °C 5: 1.) ZnBr, 2.) DBU / 1.) ether, -40 deg C to 0 deg C, 2 h, 2.) 50 deg C, 2 h View Scheme |
11-Methoxy-3,7,11-trimethyl-2,5-dioxo-dodecanoic acid isopropyl ester
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: sodium borohydride / tetrahydrofuran / 1 h / 0 °C 2: pyridine / 24 h / 25 °C 3: potassium t-butoxid, 18-Crown-6 / benzene / 0.5 h / Ambient temperature 4: sodium borohydride / propan-2-ol / 4 h / Heating 5: PBr3, LiBr, 2,4,6-collidine / 3 h / -40 - 0 °C 6: 1.) ZnBr, 2.) DBU / 1.) ether, -40 deg C to 0 deg C, 2 h, 2.) 50 deg C, 2 h View Scheme |
2-(7-Methoxy-3,7-dimethyl-octanoyl)-3-methyl-cyclopropanecarboxylic acid isopropyl ester
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium borohydride / propan-2-ol / 4 h / Heating 2: PBr3, LiBr, 2,4,6-collidine / 3 h / -40 - 0 °C 3: 1.) ZnBr, 2.) DBU / 1.) ether, -40 deg C to 0 deg C, 2 h, 2.) 50 deg C, 2 h View Scheme |
11-Methoxy-3,7,11-trimethyl-5-oxo-2-(toluene-4-sulfonyloxy)-dodecanoic acid isopropyl ester
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: potassium t-butoxid, 18-Crown-6 / benzene / 0.5 h / Ambient temperature 2: sodium borohydride / propan-2-ol / 4 h / Heating 3: PBr3, LiBr, 2,4,6-collidine / 3 h / -40 - 0 °C 4: 1.) ZnBr, 2.) DBU / 1.) ether, -40 deg C to 0 deg C, 2 h, 2.) 50 deg C, 2 h View Scheme |
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