Bicyclo[4.1.0]hept-2-ene-3-carboxaldehyde, 7,7-dimethyl-, (1R,6S)- CAS:14917-83-0 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermedia
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inquiryBicyclo[4.1.0]hept-2-ene-3-carboxaldehyde, 7,7-dimethyl-, (1R,6S)-Appearance:Off white to slight yellow solid Storage:Store in dry and cool condition Package:25kg or according to cutomer's demand Application:Chemical research/Pharmaceutical intermedi
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inquiry(4S)-4-(1-chloro-1-methylethyl)-1-cyclohexenecarboxaldehyde
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 0℃; | 94% |
With potassium tert-butylate In tetrahydrofuran at 0℃; Yield given; |
(S)-(-)-perillaldehyde
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
Conditions | Yield |
---|---|
Stage #1: (S)-(-)-perillaldehyde With hydrogen bromide; acetic acid at 0 - 25℃; for 2.5h; Stage #2: With tert-Amyl alcohol; potassium tert-butylate at 0 - 25℃; for 3h; | 45% |
(i) HBr, AcOH, (ii) KOtBu, t-amyl alcohol; Multistep reaction; | |
With potassium tert-butylate; hydrogen bromide; acetic acid Multistep reaction; |
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
(S)-1-phenyl-ethylamine
Conditions | Yield |
---|---|
Stage #1: (1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde; (S)-1-phenyl-ethylamine In ethanol for 2h; Reflux; Stage #2: With sodium tetrahydroborate In ethanol for 2h; Reflux; | 75% |
methylthiol
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
(1R,6S)-7,7-dimethyl-3-(bis(methylthio)methyl)bicyclo<4.1.0>hept-2-ene
Conditions | Yield |
---|---|
With titanium tetrachloride at -78℃; for 0.166667h; | 70% |
1.3-propanedithiol
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
(1R,6S)-7,7-dimethyl-3-(1,3-dithia-2-cyclohexyl)bicyclo<4.1.0>hept-2-ene
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane | 68% |
With boron trifluoride diethyl etherate In dichloromethane at 0℃; for 2.5h; | 46% |
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
Stage #1: (1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde; (R)-1-phenyl-ethyl-amine In ethanol for 2h; Reflux; Stage #2: With sodium tetrahydroborate In ethanol for 2h; Reflux; | 66% |
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
benzylamine
Conditions | Yield |
---|---|
Stage #1: (1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde; benzylamine In ethanol at 20℃; for 2h; Stage #2: With sodium tetrahydroborate In ethanol at 20℃; for 2h; | 62% |
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
Conditions | Yield |
---|---|
With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; tert-butyl alcohol In water Solvent; Reagent/catalyst; | 60% |
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
2-(triphenylphosphoranylidene)succinic acid 1-ethyl ester
Conditions | Yield |
---|---|
In benzene at 50℃; for 48h; | 47% |
trimethylsilyl cyanide
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
Conditions | Yield |
---|---|
With potassium cyanide; 18-crown-6 ether at 0℃; for 0.25h; |
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: KCN, 18-crown-6 / 0.25 h / 0 °C 2: aq. HCl / 5 h / Ambient temperature 3: 45 percent / methanesulfonyl chloride, triethylamine / tetrahydrofuran / -78 °C View Scheme |
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
2-<(1R,4S)-1-acetyl-1-hydroxy-4-methyl-2-cyclopenten-2-yl>-2-<(1R,6S)-7,7-dimethylbicyclo<4.1.0>hept-2-en-3-yl>-1,3-dithiacyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 46 percent / boron trifluoride etherate / CH2Cl2 / 2.5 h / 0 °C 3: 92 percent / dimethyl sulfoxide, trifluoroacetic anhydride / CH2Cl2 / 0.5 h / -78 °C 4: 11.1 g / sodium hydroxide / CH2Cl2 / 2 h / Ambient temperature 5: tetrahydrofuran / 0.5 h / -60 - 0 °C 6: aq. HCl View Scheme |
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
(1R,4S)-2-[2-((1R,6S)-7,7-Dimethyl-bicyclo[4.1.0]hept-2-en-3-yl)-[1,3]dithian-2-yl]-1-(1-ethoxy-vinyl)-4-methyl-cyclopent-2-enol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 46 percent / boron trifluoride etherate / CH2Cl2 / 2.5 h / 0 °C 3: 92 percent / dimethyl sulfoxide, trifluoroacetic anhydride / CH2Cl2 / 0.5 h / -78 °C 4: 11.1 g / sodium hydroxide / CH2Cl2 / 2 h / Ambient temperature 5: tetrahydrofuran / 0.5 h / -60 - 0 °C View Scheme |
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
(5S,7R,10R,11S,13S)-2-(methylthio)-5,12,12-trimethyl-8-oxo-7-((tert-butyldimethylsilyl)oxy)tetracyclo-<8.5.03,7.011,13>pentadeca-1,3-diene
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 70 percent / TiCl4 / 0.17 h / -78 °C 3: tetra-n-butylammonium fluoride / tetrahydrofuran / 48 h / Ambient temperature 4: DMSO, trifluoroacetic anhydride / CH2Cl2 / 4 h / -78 °C 5: DBU / diethyl ether / 3 h / 0 °C 6: 1.) CeCl3, t-BuLi / 1.) THF, -78 deg C, 5 min 7: 100 percent / KH, 18-crown-6 / tetrahydrofuran / 0.17 h 8: Et3N / CH2Cl2 / 0 °C 9: dimethyl(methylthio)sulfonium tetrafluoroborate / CH2Cl2 / -78 °C View Scheme |
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
2-<(1R,4S)-1-acetyl-4-methyl-1-(trimethylsiloxy)-2-cyclopenten-2-yl>-2-<(1R,6S)-7,7-dimethylbicyclo<4.1.0>-hept-2-en-3-yl>-1,3-dithiacyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 46 percent / boron trifluoride etherate / CH2Cl2 / 2.5 h / 0 °C 3: 92 percent / dimethyl sulfoxide, trifluoroacetic anhydride / CH2Cl2 / 0.5 h / -78 °C 4: 11.1 g / sodium hydroxide / CH2Cl2 / 2 h / Ambient temperature 5: tetrahydrofuran / 0.5 h / -60 - 0 °C 6: aq. HCl 7: 1.) potassium diisopropylamide / 1.) THF, -78 deg C, 5 min , 2.) 0 deg C, 1 h View Scheme |
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
1-{(1R,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-[((1R,6S)-7,7-dimethyl-bicyclo[4.1.0]hept-2-en-3-yl)-bis-methylsulfanyl-methyl]-4-methyl-cyclopent-2-enyl}-ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 70 percent / TiCl4 / 0.17 h / -78 °C 3: tetra-n-butylammonium fluoride / tetrahydrofuran / 48 h / Ambient temperature 4: DMSO, trifluoroacetic anhydride / CH2Cl2 / 4 h / -78 °C 5: DBU / diethyl ether / 3 h / 0 °C 6: 1.) CeCl3, t-BuLi / 1.) THF, -78 deg C, 5 min 7: 100 percent / KH, 18-crown-6 / tetrahydrofuran / 0.17 h View Scheme |
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
(5S,7R,10R,11S,13S)-2-(1,5,6-trithia-1-heptyl)-5,12,12-trimethyl-8-oxo-7-(trimethylsiloxy)tetracyclo<8.5.0.03,7.011,13>pentadeca-1,3-diene
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 46 percent / boron trifluoride etherate / CH2Cl2 / 2.5 h / 0 °C 3: 92 percent / dimethyl sulfoxide, trifluoroacetic anhydride / CH2Cl2 / 0.5 h / -78 °C 4: 11.1 g / sodium hydroxide / CH2Cl2 / 2 h / Ambient temperature 5: tetrahydrofuran / 0.5 h / -60 - 0 °C 6: aq. HCl 7: 1.) potassium tert-butoxide, LDA / 1.) THF, 0 deg C, 15 min, 2.) from -78 deg C to 0 deg C, 1 h 8: 1 percent / CH2Cl2 / 1.5 h / -78 °C View Scheme |
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
<(1'S,2'R,3'S,4'S)-1'-hydroxy-3'-(phenylsulfonyl)-4'-methylcyclopent-2'-yl><(1"R,6"S)-7",7"-dimethylbicyclo<4.1.0>hept-2"-en-3"-yl>bis(methylthio)methane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 70 percent / TiCl4 / 0.17 h / -78 °C 3: tetra-n-butylammonium fluoride / tetrahydrofuran / 48 h / Ambient temperature View Scheme |
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
(2R,3S,4S)-3-Benzenesulfonyl-2-[((1R,6S)-7,7-dimethyl-bicyclo[4.1.0]hept-2-en-3-yl)-bis-methylsulfanyl-methyl]-4-methyl-cyclopentanone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 70 percent / TiCl4 / 0.17 h / -78 °C 3: tetra-n-butylammonium fluoride / tetrahydrofuran / 48 h / Ambient temperature 4: DMSO, trifluoroacetic anhydride / CH2Cl2 / 4 h / -78 °C View Scheme |
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
2-<(1R,4S)-1-acetyl-4-methyl-1-(tertbutyldimethylsiloxy)-2-cyclopenten-2-yl>-2-<(1R,6S)-7,7-dimethylbicyclo<4.1.0>hept-2-en-3-yl>-1,3-dithiacyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 46 percent / boron trifluoride etherate / CH2Cl2 / 2.5 h / 0 °C 3: 92 percent / dimethyl sulfoxide, trifluoroacetic anhydride / CH2Cl2 / 0.5 h / -78 °C 4: 11.1 g / sodium hydroxide / CH2Cl2 / 2 h / Ambient temperature 5: tetrahydrofuran / 0.5 h / -60 - 0 °C 6: aq. HCl 7: 39 percent / pyridine / CH2Cl2 / 12 h / Ambient temperature View Scheme |
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
2-<(1R,4S)-4-methyl-1-(trimethylsiloxy)-1-(1-(trimetylsiloxy)vinyl)-2-cyclopenten-2-yl>-2-<(1R,6S)-7,7-dimethylbicyclo<4.1.0>hept-2-yl>-1,3-dithiacyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 46 percent / boron trifluoride etherate / CH2Cl2 / 2.5 h / 0 °C 3: 92 percent / dimethyl sulfoxide, trifluoroacetic anhydride / CH2Cl2 / 0.5 h / -78 °C 4: 11.1 g / sodium hydroxide / CH2Cl2 / 2 h / Ambient temperature 5: tetrahydrofuran / 0.5 h / -60 - 0 °C 6: aq. HCl 7: 1.) potassium tert-butoxide, LDA / 1.) THF, 0 deg C, 15 min, 2.) from -78 deg C to 0 deg C, 1 h View Scheme |
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
(1R,6S)-3-{[(3S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-5-(1-trimethylsilanyloxy-vinyl)-cyclopent-1-enyl]-bis-methylsulfanyl-methyl}-7,7-dimethyl-bicyclo[4.1.0]hept-2-ene
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 70 percent / TiCl4 / 0.17 h / -78 °C 3: tetra-n-butylammonium fluoride / tetrahydrofuran / 48 h / Ambient temperature 4: DMSO, trifluoroacetic anhydride / CH2Cl2 / 4 h / -78 °C 5: DBU / diethyl ether / 3 h / 0 °C 6: 1.) CeCl3, t-BuLi / 1.) THF, -78 deg C, 5 min 7: 100 percent / KH, 18-crown-6 / tetrahydrofuran / 0.17 h 8: Et3N / CH2Cl2 / 0 °C View Scheme |
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
2-<(2R,3S,4S)-4-methyl-1-oxo-3-(phenylsulfonyl)-2-cyclopentyl>-2-<(1R,6S)-7,7-dimethylbicyclo<4.1.0>hept-2-en-3-yl>-1,3-dithiacyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 46 percent / boron trifluoride etherate / CH2Cl2 / 2.5 h / 0 °C 3: 92 percent / dimethyl sulfoxide, trifluoroacetic anhydride / CH2Cl2 / 0.5 h / -78 °C View Scheme |
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
2-<(1'S,2'R,3'R,4'S')-1'-((tert-butyldimethylsilyl)oxy)-4'-methyl-3'-(phenylsulfonyl)cyclopent-2'-yl>-3-(bis(methylthio)methyl)-(1R,6S)-7,7-dimethylbicyclo<4.1.0>hept-3-ene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 70 percent / TiCl4 / 0.17 h / -78 °C 2: 1.) lithium diisopropylamide (LDA), HMPA / 1.) THF, 30 min, 2.) 15 min View Scheme | |
Multi-step reaction with 2 steps 1: 70 percent / TiCl4 / 0.17 h / -78 °C View Scheme |
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
{(1S,2R,3S,4S)-3-Benzenesulfonyl-2-[((1R,6S)-7,7-dimethyl-bicyclo[4.1.0]hept-2-en-3-yl)-bis-methylsulfanyl-methyl]-4-methyl-cyclopentyloxy}-tert-butyl-dimethyl-silane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 70 percent / TiCl4 / 0.17 h / -78 °C View Scheme |
(1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde
2-<(4S)-4-methyl-1-oxo-2-cyclopenten-2-yl>-2-<(1R,6S)-7,7-dimethylbicyclo<4.1.0>hept-2-en-3-yl>-1,3-dithiacyclohexane
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 46 percent / boron trifluoride etherate / CH2Cl2 / 2.5 h / 0 °C 3: 92 percent / dimethyl sulfoxide, trifluoroacetic anhydride / CH2Cl2 / 0.5 h / -78 °C 4: 11.1 g / sodium hydroxide / CH2Cl2 / 2 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1: 68 percent / boron trifluoride etherate / CH2Cl2 2: 65 percent / methyllithium, n-butyllithium / tetrahydrofuran / -78 °C 3: 1.) Me2SO/TFAA, 2.) (C2H5)3N, 3.) NaOH View Scheme | |
Multi-step reaction with 2 steps 1: 68 percent / boron trifluoride etherate / CH2Cl2 View Scheme |
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