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CAS No.: | 77087-34-4 |
---|---|
Name: | (4S)-4-hydroxy-3-methyl-2-prop-2-ynyl-cyclopent-2-en-1-one |
Article Data: | 3 |
Molecular Structure: | |
Formula: | C9H10 O2 |
Molecular Weight: | 150.177 |
Synonyms: | 2-Cyclopenten-1-one,4-hydroxy-3-methyl-2-(2-propynyl)-, (4S)- (9CI); 2-Cyclopenten-1-one, 4-hydroxy-3-methyl-2-(2-propynyl)-,(S)-; (S)-4-Hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one;(S)-Propargylone |
Density: | 1.161g/cm3 |
Boiling Point: | 284.6°C at 760 mmHg |
Flash Point: | 119.4°C |
PSA: | 37.30000 |
LogP: | 0.65990 |
C9H11BO4
A
(R)-4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one
B
(S)-4-hydroxy-3-methyl-2-(2-propynyl)-cyclopent-2-ene-1-one
Conditions | Yield |
---|---|
With water; calcium carbonate at 85℃; for 4h; Yield given. Yields of byproduct given; |
(+/-)-4-acetoxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one
A
(R)-4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one
B
(S)-4-hydroxy-3-methyl-2-(2-propynyl)-cyclopent-2-ene-1-one
Conditions | Yield |
---|---|
With Arthrobacter lipase; water; methanesulfonyl chloride Product distribution; Multistep reaction; methodology for preparation of secondary (S)-alcohol from the corresponding racemic acetate; further acetates; |
(S)-4-acetoxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one
A
(R)-4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one
B
(S)-4-hydroxy-3-methyl-2-(2-propynyl)-cyclopent-2-ene-1-one
Conditions | Yield |
---|---|
With water; nitric acid at 80℃; |
(S)-4-acetoxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one
(S)-4-hydroxy-3-methyl-2-(2-propynyl)-cyclopent-2-ene-1-one
Conditions | Yield |
---|---|
With sulfuric acid at 80℃; for 3h; or 2.5percent aq. HNO3; | 96 % Chromat. |
Multi-step reaction with 3 steps 1: H2O, 2,5percent HNO3 / 80 °C 2: 97 percent Chromat. / fuming HNO3 3: H2O, CaCO3 / 4 h / 85 °C View Scheme | |
Multi-step reaction with 3 steps 1: H2O, 2,5percent HNO3 / 80 °C 2: 97 percent Chromat. 3: H2O, CaCO3 / 4 h / 85 °C View Scheme |
(R)-2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl nitrate
A
(R)-4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one
B
(S)-4-hydroxy-3-methyl-2-(2-propynyl)-cyclopent-2-ene-1-one
Conditions | Yield |
---|---|
With water; calcium carbonate at 85℃; for 4h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With water; calcium carbonate at 85℃; for 4h; Yield given. Yields of byproduct given; | |
With water; calcium carbonate at 85℃; for 4h; Product distribution; different amounts of CaCO3; or mesylate instead of nitrate; |
(R)-2-methyl-4-oxo-3-(2-propynyl)-2-cyclopentenyl methanesulfonate
A
(R)-4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one
B
(S)-4-hydroxy-3-methyl-2-(2-propynyl)-cyclopent-2-ene-1-one
Conditions | Yield |
---|---|
With water; calcium carbonate at 85℃; for 4h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With water; calcium carbonate at 85℃; for 4h; Yield given. Yields of byproduct given; |
C9H11BO4
(S)-4-hydroxy-3-methyl-2-(2-propynyl)-cyclopent-2-ene-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: H2O, CaCO3 / 4 h / 85 °C 2: fuming HNO3 3: H2O, 2,5percent HNO3 / 80 °C View Scheme | |
Multi-step reaction with 3 steps 1: H2O, CaCO3 / 4 h / 85 °C 2: 97 percent Chromat. / fuming HNO3 3: H2O, CaCO3 / 4 h / 85 °C View Scheme | |
Multi-step reaction with 3 steps 1: H2O, CaCO3 / 4 h / 85 °C 3: H2O, 2,5percent HNO3 / 80 °C View Scheme | |
Multi-step reaction with 3 steps 1: H2O, CaCO3 / 4 h / 85 °C 2: 97 percent Chromat. 3: H2O, CaCO3 / 4 h / 85 °C View Scheme |
(R)-4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one
(S)-4-hydroxy-3-methyl-2-(2-propynyl)-cyclopent-2-ene-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: fuming HNO3 2: H2O, 2,5percent HNO3 / 80 °C View Scheme | |
Multi-step reaction with 2 steps 1: 97 percent Chromat. / fuming HNO3 2: H2O, CaCO3 / 4 h / 85 °C View Scheme | |
Multi-step reaction with 2 steps 2: H2O, 2,5percent HNO3 / 80 °C View Scheme |
(+/-)-4-acetoxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one
(S)-4-hydroxy-3-methyl-2-(2-propynyl)-cyclopent-2-ene-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 46 percent / arthrobacter lipase 2: fuming HNO3 3: H2O, 2,5percent HNO3 / 80 °C View Scheme | |
Multi-step reaction with 3 steps 1: 46 percent / arthrobacter lipase 2: 97 percent Chromat. / fuming HNO3 3: H2O, CaCO3 / 4 h / 85 °C View Scheme | |
Multi-step reaction with 4 steps 1: 46 percent / arthrobacter lipase 2: H2O, 2,5percent HNO3 / 80 °C 3: 97 percent Chromat. / fuming HNO3 4: H2O, CaCO3 / 4 h / 85 °C View Scheme |
(R)-2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl nitrate
(S)-4-hydroxy-3-methyl-2-(2-propynyl)-cyclopent-2-ene-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: H2O, CaCO3 / 4 h / 85 °C 3: H2O, 2,5percent HNO3 / 80 °C View Scheme | |
Multi-step reaction with 3 steps 1: H2O, CaCO3 / 4 h / 85 °C 2: 97 percent Chromat. 3: H2O, CaCO3 / 4 h / 85 °C View Scheme | |
Multi-step reaction with 3 steps 1: H2O, CaCO3 / 4 h / 85 °C / different amounts of CaCO3; or mesylate instead of nitrate 2: triethylamine / acetone / 2 h / -15 °C 3: H2O, CaCO3 / 4 h / 85 °C View Scheme |