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204254-96-6

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CAS No.: 204254-96-6
Name: (1S,5R,6S)-Ethyl 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate
Article Data: 7
Molecular Structure:
Molecular Structure of 204254-96-6 ((1S,5R,6S)-Ethyl 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate)
Formula: C14H22O4
Molecular Weight: 254.326
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;
EINECS: 429-020-1
Density: 1.09 g/cm3
Melting Point: 56-57 °C
Boiling Point: 336.495 °C at 760 mmHg
Flash Point: 145.075 °C
Appearance: White to off-white solid
PSA: 48.06000
LogP: 2.22080
Related products
Synthetic route
204254-92-2

ethyl (3R,4R,5R)-3-(1-ethyl-propoxy)-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate

204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
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
204254-90-0

ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate

204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
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;
204254-84-2

ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate

204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
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
204254-81-9

ethyl (3aR,5S,7R,7aR)-5-hydroxy-7-methanesulfonyloxy-2,2-dimethylhexahydrobenzo[1,3]dioxole-5-carboxylate

204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
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
77-95-2

D-(-)-quinic acid

204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
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
77-76-9

2,2-dimethoxy-propane

204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
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
32384-42-2

(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone

204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
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
107-11-9

1-amino-2-propene

204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

312904-11-3

ethyl (3R,4S,5R)-5-N-allyllamino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate

Conditions
ConditionsYield
With magnesium bromide In acetonitrile at 55℃; for 16h;97%
75-64-9

tert-butylamine

204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

A

1151665-78-9

C14H20O3

B

C14H23ClO4

C

651324-04-8

(3R,4S,5R)-[5-(tert-butylamino)-4-hydroxy-3-(pent-3-yloxy)]cyclohex-1-ene-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
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%
...Expand
75-05-8

acetonitrile

204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

1443055-47-7

(3R,4S,5R)-ethyl 5-acetylamino-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

Conditions
ConditionsYield
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%
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Chemistry

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

Specification

 (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 .