methyl 7-<3(R)-(acetyloxy)-5-oxo-1-cyclopenten-1-yl>heptanoate
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
With guanidine nitrate | 98% |
With guanidine nitrate In methanol at 0℃; |
7-{5-oxo-3-[(tetrahydro-2H-pyran-2-yl)oxy]cyclopent-1-en-1-yl}heptanoic acid methyl ester
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
With acetic acid In tetrahydrofuran; water for 24h; Ambient temperature; | 88% |
Benzoic acid (R)-4-hydroxy-2-(6-methoxycarbonyl-hexyl)-3-oxo-cyclopent-1-enyl ester
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
(i) Al, (ii) AcOH; Multistep reaction; |
7-((R)-4-Hydroxy-2-isopropoxy-5-oxo-cyclopent-1-enyl)-heptanoic acid methyl ester
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
(i) Al, (ii) AcOH; Multistep reaction; |
7-{3-[(tert-butyldimethylsilanyl)oxy]-5-oxocyclopent-1-en-1-yl}heptanoic acid methyl ester
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran |
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
With acetic acid |
7-((S)-3-Methanesulfonyloxy-5-oxo-cyclopent-1-enyl)-heptanoic acid methyl ester
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
With guanidine nitrate In methanol at 0℃; for 0.25h; Substitution; Mitsunobu inversion; |
8-(furan-2-yl)-8-oxooctanoic acid methyl ester
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: aq. phosphate buffer; dioxane / 30 h / pH 8 / Heating 2: 46 percent / PPL 3: 98 percent / guanidine View Scheme |
suberic acid monomethyl ester
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: aq. phosphate buffer; dioxane / 30 h / pH 8 / Heating 2: 46 percent / PPL 3: 98 percent / guanidine View Scheme |
methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)heptanoate
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 46 percent / PPL 2: 98 percent / guanidine View Scheme | |
Multi-step reaction with 2 steps 1: lipase (PPL) 2: quanidine / methanol / 0 °C View Scheme |
methyl 7-(2-hydroxy-5-oxocyclopent-3-enyl)heptanoate
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aq. phosphate buffer; dioxane / 30 h / pH 8 / Heating 2: 46 percent / PPL 3: 98 percent / guanidine View Scheme |
methyl 8-(2-furyl)-8-hydroxy-octanoate
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: aq. phosphate buffer; dioxane / 30 h / pH 8 / Heating 2: 46 percent / PPL 3: 98 percent / guanidine View Scheme |
methyl 7-<3(S)-(hydroxy)-5-oxo-1-cyclopenten-1-yl>heptanoate
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 / -10 °C 2: guanidine / methanol / 0.25 h / 0 °C View Scheme |
C7H13IO2Zn
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1) CuCN / 2) THF, -78 deg C up to r.t. 2: n-Bu4NF / tetrahydrofuran View Scheme |
(3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-2-methylene-cyclopentanone
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1) CuCN / 2) THF, -78 deg C up to r.t. 2: n-Bu4NF / tetrahydrofuran View Scheme |
2-(6-Methoxycarbonylhexyl)-cyclopentan-1,3,4-trion
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: (microbiological transformation) 2: Et3N 3: (i) Al, (ii) AcOH View Scheme | |
Multi-step reaction with 3 steps 1: (microbiological transformation) 2: K2CO3 3: (i) Al, (ii) AcOH View Scheme |
2-(6'-carbomethoxyhexyl)-4(R)-hydroxy-cyclopentane-1,3-dione
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Et3N 2: (i) Al, (ii) AcOH View Scheme | |
Multi-step reaction with 2 steps 1: K2CO3 2: (i) Al, (ii) AcOH View Scheme |
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
tert-butyldimethylsilyl chloride
7-{3-[(tert-butyldimethylsilanyl)oxy]-5-oxocyclopent-1-en-1-yl}heptanoic acid methyl ester
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide | 98% |
With 1H-imidazole In N,N-dimethyl-formamide for 0.5h; Ambient temperature; | 95% |
With 1H-imidazole; triethylamine In N,N-dimethyl-formamide | 84% |
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
t-butyldimethylsiyl triflate
7-{3-[(tert-butyldimethylsilanyl)oxy]-5-oxocyclopent-1-en-1-yl}heptanoic acid methyl ester
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine In dichloromethane at -78 - 20℃; for 15h; silylation; | 89% |
With 2,6-dimethylpyridine In dichloromethane at -78 - 20℃; for 15.5h; |
triethylsilyl chloride
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
methyl-7-[5-oxo-3(R)-[(triethylsilyl)oxy]-1-cyclopenten-1yl]-heptanoate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; Etherification; | 88% |
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
(-)-1-mercapto-2(S)-heptanol
A
5-(6-methoxycarbonylhexyl)-3-<2(S)-hydroxyheptylthio>-2-cyclopentenone
B
13,14-dihydro-13-thia-prostaglandin-E1 methylester
Conditions | Yield |
---|---|
With triethylamine In methanol for 48h; Ambient temperature; | A 7.9% B 12.3% C n/a |
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
n-hexylmagnesium bromide
(-)-methyl 7-[(1S,2R)-2-hexyl-5-oxocyclopent-3-enyl]heptanoate
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether at 0 - 30℃; for 36h; |
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether / 36 h / 0 - 30 °C 2: L-selectride / tetrahydrofuran; 2-methyl-propan-2-ol / 1 h / -78 °C View Scheme |
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
methyl 7-(5-but-3-enyl-2-hydroxy-4-(1,1,2,2-tetramethyl-1-silapropoxy)cyclopentyl)heptanoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 89 percent / 2,6-lutidine / CH2Cl2 / 15 h / -78 - 20 °C 2.1: Mg; I2 / tetrahydrofuran / 3 h / Heating 2.2: 71 percent / CuBr*DMS / tetrahydrofuran / 2.25 h / -78 - 20 °C View Scheme |
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
7-[(1R,2R,3R,5S)-2-But-3-enyl-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-cyclopentyl]-heptanoic acid methyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 89 percent / 2,6-lutidine / CH2Cl2 / 15 h / -78 - 20 °C 2.1: Mg; I2 / tetrahydrofuran / 3 h / Heating 2.2: 71 percent / CuBr*DMS / tetrahydrofuran / 2.25 h / -78 - 20 °C 3.1: 61 percent / NaBH4 / methanol / 25 h / -78 - -40 °C View Scheme |
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
methyl 7-(2-hydroxy-5-(2-(2-oxiranyl)ethyl)-4-(1,1,2,2-tetramethyl-1-silapropoxy)cyclopentyl)heptanoate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 89 percent / 2,6-lutidine / CH2Cl2 / 15 h / -78 - 20 °C 2.1: Mg; I2 / tetrahydrofuran / 3 h / Heating 2.2: 71 percent / CuBr*DMS / tetrahydrofuran / 2.25 h / -78 - 20 °C 3.1: 61 percent / NaBH4 / methanol / 25 h / -78 - -40 °C 4.1: 73 percent / m-CPBA; sodium bicarbonate / CH2Cl2 / 20 h / 20 °C View Scheme |
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[3-hydroxy-4-(thiazol-2-ylsulfanyl)-butyl]-cyclopentyl}-heptanoic acid methyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: 89 percent / 2,6-lutidine / CH2Cl2 / 15 h / -78 - 20 °C 2.1: Mg; I2 / tetrahydrofuran / 3 h / Heating 2.2: 71 percent / CuBr*DMS / tetrahydrofuran / 2.25 h / -78 - 20 °C 3.1: 61 percent / NaBH4 / methanol / 25 h / -78 - -40 °C 4.1: 73 percent / m-CPBA; sodium bicarbonate / CH2Cl2 / 20 h / 20 °C 5.1: triethylamine / benzene / 20 h / 0 - 20 °C 6.1: HF/pyridine / acetonitrile / 3 h / 0 °C View Scheme |
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: 89 percent / 2,6-lutidine / CH2Cl2 / 15 h / -78 - 20 °C 2.1: Mg; I2 / tetrahydrofuran / 3 h / Heating 2.2: 71 percent / CuBr*DMS / tetrahydrofuran / 2.25 h / -78 - 20 °C 3.1: 61 percent / NaBH4 / methanol / 25 h / -78 - -40 °C 4.1: 73 percent / m-CPBA; sodium bicarbonate / CH2Cl2 / 20 h / 20 °C 5.1: triethylamine / benzene / 20 h / 0 - 20 °C 6.1: HF/pyridine / acetonitrile / 3 h / 0 °C View Scheme |
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-(3-hydroxy-4-phenylsulfanyl-butyl)-cyclopentyl]-heptanoic acid methyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: 89 percent / 2,6-lutidine / CH2Cl2 / 15 h / -78 - 20 °C 2.1: Mg; I2 / tetrahydrofuran / 3 h / Heating 2.2: 71 percent / CuBr*DMS / tetrahydrofuran / 2.25 h / -78 - 20 °C 3.1: 61 percent / NaBH4 / methanol / 25 h / -78 - -40 °C 4.1: 73 percent / m-CPBA; sodium bicarbonate / CH2Cl2 / 20 h / 20 °C 5.1: triethylamine / benzene / 20 h / 0 - 20 °C 6.1: HF/pyridine / acetonitrile / 3 h / 0 °C View Scheme |
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: 89 percent / 2,6-lutidine / CH2Cl2 / 15 h / -78 - 20 °C 2.1: Mg; I2 / tetrahydrofuran / 3 h / Heating 2.2: 71 percent / CuBr*DMS / tetrahydrofuran / 2.25 h / -78 - 20 °C 3.1: 61 percent / NaBH4 / methanol / 25 h / -78 - -40 °C 4.1: 73 percent / m-CPBA; sodium bicarbonate / CH2Cl2 / 20 h / 20 °C 5.1: triethylamine / benzene / 20 h / 0 - 20 °C 6.1: HF/pyridine / acetonitrile / 3 h / 0 °C 7.1: LiOH / tetrahydrofuran; H2O / 20 °C View Scheme |
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: 89 percent / 2,6-lutidine / CH2Cl2 / 15 h / -78 - 20 °C 2.1: Mg; I2 / tetrahydrofuran / 3 h / Heating 2.2: 71 percent / CuBr*DMS / tetrahydrofuran / 2.25 h / -78 - 20 °C 3.1: 61 percent / NaBH4 / methanol / 25 h / -78 - -40 °C 4.1: 73 percent / m-CPBA; sodium bicarbonate / CH2Cl2 / 20 h / 20 °C 5.1: magnesium perchlorate / tetrahydrofuran / 3 h / Heating 6.1: HF/pyridine / acetonitrile / 5 h / 0 °C 7.1: 57 percent / LiOH / tetrahydrofuran; H2O / 20 °C View Scheme |
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-(3-hydroxy-4-phenylamino-butyl)-cyclopentyl]-heptanoic acid methyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: 89 percent / 2,6-lutidine / CH2Cl2 / 15 h / -78 - 20 °C 2.1: Mg; I2 / tetrahydrofuran / 3 h / Heating 2.2: 71 percent / CuBr*DMS / tetrahydrofuran / 2.25 h / -78 - 20 °C 3.1: 61 percent / NaBH4 / methanol / 25 h / -78 - -40 °C 4.1: 73 percent / m-CPBA; sodium bicarbonate / CH2Cl2 / 20 h / 20 °C 5.1: magnesium perchlorate / tetrahydrofuran / 3 h / Heating 6.1: HF/pyridine / acetonitrile / 5 h / 0 °C View Scheme |
(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: 89 percent / 2,6-lutidine / CH2Cl2 / 15 h / -78 - 20 °C 2.1: Mg; I2 / tetrahydrofuran / 3 h / Heating 2.2: 71 percent / CuBr*DMS / tetrahydrofuran / 2.25 h / -78 - 20 °C 3.1: 61 percent / NaBH4 / methanol / 25 h / -78 - -40 °C 4.1: 73 percent / m-CPBA; sodium bicarbonate / CH2Cl2 / 20 h / 20 °C 5.1: triethylamine / benzene / 20 h / 0 - 20 °C 6.1: HF/pyridine / acetonitrile / 3 h / 0 °C 7.1: LiOH / tetrahydrofuran; H2O / 20 °C View Scheme |
The Methyl (R)-(+)-3-hydroxy-5-oxo-1-cyclopentene-1-heptanoate ,its cas register number is 41138-61-8.It also can be called as 1-Cyclopentene-1-heptanoicacid, 3-hydroxy-5-oxo-, methyl ester, (3R)- and the Systematic name about this chemicals is methyl 7-[(3R)-3-hydroxy-5-oxocyclopent-1-en-1-yl]heptanoate .It belongs to the following product categories, such as Chiral Building Blocks, Esters, Organic Building Blocks and so on.
Following are the chemical properties about Methyl (R)-(+)-3-hydroxy-5-oxo-1-cyclopentene-1-heptanoate :(1)#H bond acceptors: 4; (2)#H bond donors: 1; (3)#Freely Rotating Bonds: 9; (4)Polar Surface Area: 63.6Å2; (5)Index of Refraction: 1.504; (6)Molar Refractivity: 63.278 cm3; (7)Molar Volume: 213.581 cm3; (8)Polarizability: 25.085x10-24cm3; (9)Surface Tension: 44.208 dyne/cm; (10)Enthalpy of Vaporization: 72.454 kJ/mol; (11)Vapour Pressure: 0 mmHg at 25°C
This chemicals can be described computed from structure:
(1)SMILES: O=C1\C(=C/[C@H](O)C1)CCCCCCC(=O)OC
(2)InChI: InChI=1/C13H20O4/c1-17-13(16)7-5-3-2-4-6-10-8-11(14)9-12(10)15/h8,11,14H,2-7,9H2,1H3/t11-/m0/s1
(3)InChIKey: PQKUWAVOSCVDCT-NSHDSACABK
(4)Std. InChI: InChI=1S/C13H20O4/c1-17-13(16)7-5-3-2-4-6-10-8-11(14)9-12(10)15/h8,11,14H,2-7,9H2,1H3/t11-/m0/s1
(5)Std. InChIKey: PQKUWAVOSCVDCT-NSHDSACASA-N
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