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Name |
(1S,5R,6S)-Ethyl 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate |
EINECS | 429-020-1 |
CAS No. | 204254-96-6 | Density | 1.09 g/cm3 |
PSA | 48.06000 | LogP | 2.22080 |
Solubility | N/A | Melting Point |
56-57 °C |
Formula | C14H22O4 | Boiling Point | 336.495 °C at 760 mmHg |
Molecular Weight | 254.326 | Flash Point | 145.075 °C |
Transport Information | N/A | Appearance | White to off-white solid |
Safety | Risk Codes | N/A | |
Molecular Structure | Hazard Symbols | N/A | |
Synonyms |
[1S-(1a,5b,6a)]-5-(1-Ethylpropoxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester;Ethyl(3r,4s,5s)-4,5-Epoxy-3-(1-Ethyl-Propoxy)-Cyclohex-1-Ene-1-Carboxylate; |
Article Data | 7 |
ethyl (3R,4R,5R)-3-(1-ethyl-propoxy)-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethanol; water at 60℃; for 2h; | |
With potassium hydrogencarbonate In ethanol at 60℃; for 1h; | 2 g |
With sodium hydrogencarbonate In ethanol at 60 - 65℃; for 1.5h; Inert atmosphere; Industrial scale; Large scale; | 1.55 kg |
ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; potassium hydrogencarbonate 1.) dichloromethane, -20 - -10 deg C, 0.2 h, 2.) ethanol, water, 55-65 deg C, 1 h; Yield given. Multistep reaction; | |
Stage #1: ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate With trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex In dichloromethane at -30 - -20℃; for 1h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water at 20℃; for 12h; Stage #3: With potassium hydrogencarbonate In ethanol; water at 55 - 65℃; for 2h; |
ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / perchloric acid 2: 1.) BH3-SMe2, trimethylsilyl trifluoromethanesulfonate, 2.) potassium hydroden carbonate / 1.) dichloromethane, -20 - -10 deg C, 0.2 h, 2.) ethanol, water, 55-65 deg C, 1 h View Scheme | |
Multi-step reaction with 2 steps 1.1: perchloric acid / 18 h 2.1: dimethylsulfide borane complex; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -30 - -20 °C 2.2: 12 h / 20 °C 2.3: 2 h / 55 - 65 °C View Scheme |
ethyl (3aR,5S,7R,7aR)-5-hydroxy-7-methanesulfonyloxy-2,2-dimethylhexahydrobenzo[1,3]dioxole-5-carboxylate
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: pyridine; sulfuryl dichloride / dichloromethane / -30 - -20 °C 2.1: perchloric acid / 18 h 3.1: dimethylsulfide borane complex; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -30 - -20 °C 3.2: 12 h / 20 °C 3.3: 2 h / 55 - 65 °C View Scheme |
D-(-)-quinic acid
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / acetone / 2 h / Reflux; Large scale 2.1: ethanol / 2 h / 20 °C 2.2: 1 h / 0 - 10 °C 3.1: pyridine; sulfuryl dichloride / dichloromethane / -30 - -20 °C 4.1: perchloric acid / 18 h 5.1: dimethylsulfide borane complex; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -30 - -20 °C 5.2: 12 h / 20 °C 5.3: 2 h / 55 - 65 °C View Scheme |
2,2-dimethoxy-propane
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / acetone / 2 h / Reflux; Large scale 2.1: ethanol / 2 h / 20 °C 2.2: 1 h / 0 - 10 °C 3.1: pyridine; sulfuryl dichloride / dichloromethane / -30 - -20 °C 4.1: perchloric acid / 18 h 5.1: dimethylsulfide borane complex; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -30 - -20 °C 5.2: 12 h / 20 °C 5.3: 2 h / 55 - 65 °C View Scheme |
(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: ethanol / 2 h / 20 °C 1.2: 1 h / 0 - 10 °C 2.1: pyridine; sulfuryl dichloride / dichloromethane / -30 - -20 °C 3.1: perchloric acid / 18 h 4.1: dimethylsulfide borane complex; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -30 - -20 °C 4.2: 12 h / 20 °C 4.3: 2 h / 55 - 65 °C View Scheme |
1-amino-2-propene
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
ethyl (3R,4S,5R)-5-N-allyllamino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate
Conditions | Yield |
---|---|
With magnesium bromide In acetonitrile at 55℃; for 16h; | 97% |
tert-butylamine
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
A
C14H20O3
C
(3R,4S,5R)-[5-(tert-butylamino)-4-hydroxy-3-(pent-3-yloxy)]cyclohex-1-ene-1-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: tert-butylamine With magnesium chloride In toluene at 10℃; for 1h; Stage #2: (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester In toluene at 60℃; for 48h; Temperature; Time; | A 1.65% B 0.83% C 95.8% |
acetonitrile
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
(3R,4S,5R)-ethyl 5-acetylamino-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate
Conditions | Yield |
---|---|
Stage #1: acetonitrile; (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester With boron trifluoride diethyl etherate at 0℃; for 1.16667h; Stage #2: With water In acetonitrile at 0 - 20℃; for 4h; Stage #3: With potassium carbonate In acetonitrile at 20℃; for 36h; diastereoselective reaction; | 95% |
Molecular structure of 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate (CAS NO.204254-96-6) is:
Product Name: 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate
CAS Registry Number: 204254-96-6
Systematic Name: ethyl 5-(1-ethylpropoxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylate
Empirical Formula: C14H22O4
Molecular Weight: 254.3221
Index of Refraction: 1.491
Molar Refractivity: 67.71 cm3
Molar Volume: 233.4 cm3
Surface Tension: 36.4 dyne/cm
Density: 1.08 g/cm3
Flash Point: 145.1 °C
Enthalpy of Vaporization: 57.97 kJ/mol
Boiling Point: 336.5 °C at 760 mmHg
Vapour Pressure: 0.000112 mmHg at 25°C
(1S,5R,6S)-Ethyl 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate , its cas register number is 204254-96-6. It also can be called [1S-(1a,5b,6a)]-5-(1-Ethylpropoxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester ; Ethyl(3r,4s,5s)-4,5-Epoxy-3-(1-Ethyl-Propoxy)-Cyclohex-1-Ene-1-Carboxylate .