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CAS No.: | 243984-11-4 |
---|---|
Name: | RESATORVID |
Article Data: | 6 |
Molecular Structure: | |
Formula: | C15H17ClFNO4S |
Molecular Weight: | 361.822 |
Synonyms: | Resatorvid;(6R)-6-[[(2-Chloro-4-fluorophenyl)amino]sulfonyl]-1-cyclohexene-1-carboxylic acid ethyl ester; |
Density: | 1.39 g/cm3 |
Melting Point: | 68-69 °C |
Boiling Point: | 461.958 °C at 760 mmHg |
Flash Point: | 233.184 °C |
PSA: | 80.85000 |
LogP: | 4.41660 |
(6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylic acid
ethanol
ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
Conditions | Yield |
---|---|
With sulfuric acid for 19h; Heating; | 72% |
ethyl (6R)-6-{[[(2S)-2-(acetyloxy)-2-phenylacetyl]-(2-chloro-4-fluorophenyl)amino]sulfonyl}cyclohex-1-ene-1-carboxylate
A
ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran at 0℃; for 2h; | A 68% B n/a |
acetoxymethyl (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate
ethanol
ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
Conditions | Yield |
---|---|
With sulfuric acid for 25h; Heating; | 65% |
(1'S)-1'phenylethyl (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate
ethanol
ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
Conditions | Yield |
---|---|
With sulfuric acid for 26h; Heating; | 37% |
ethyl (6RS)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate
A
ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
Conditions | Yield |
---|---|
HPLC-CHIRALPAK AD; | A 634 mg B 681 mg |
A
ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran at 0℃; for 2h; Title compound not separated from byproducts.; |
ethyl 2-(chlorosulfonyl)cyclohex-1-ene-1-carboxylate
ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 78 percent / Et3N / ethyl acetate 2: 634 mg / HPLC-CHIRALPAK AD View Scheme |
2-(ethoxycarbonyl)cyclohex-1-ene-1-sulfonic acid
ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: SOCl2 / 14 h / Heating 2: 78 percent / Et3N / ethyl acetate 3: 634 mg / HPLC-CHIRALPAK AD View Scheme |
(6RS)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylic acid
ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 72 percent / Cs2CO3; tetrabutylammonium iodide / acetonitrile / 2.5 h / 52 - 55 °C 2: Lipase PS-D / acetone; H2O / 17.5 h / 28 °C 3: 72 percent / H2SO4 / 19 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 72 percent / Cs2CO3; tetrabutylammonium iodide / acetonitrile / 2.5 h / 52 - 55 °C 2: 48 percent / Lipase PS-D / acetone; H2O / 17.5 h / 28 °C 3: 65 percent / H2SO4 / 25 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 32 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 7 h 2: 84 percent / H2; AcOH / Pd/C / 2 h / atmospheric pressure 3: 72 percent / H2SO4 / 19 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 32 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 6 h 2: 37 percent / H2SO4 / 26 h / Heating View Scheme |
ethyl (6RS)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate
ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 74 percent / Ba(OH)2*8H2O / acetonitrile / 1 h / 60 °C 2: 72 percent / Cs2CO3; tetrabutylammonium iodide / acetonitrile / 2.5 h / 52 - 55 °C 3: Lipase PS-D / acetone; H2O / 17.5 h / 28 °C 4: 72 percent / H2SO4 / 19 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1: 74 percent / Ba(OH)2*8H2O / acetonitrile / 1 h / 60 °C 2: 72 percent / Cs2CO3; tetrabutylammonium iodide / acetonitrile / 2.5 h / 52 - 55 °C 3: 48 percent / Lipase PS-D / acetone; H2O / 17.5 h / 28 °C 4: 65 percent / H2SO4 / 25 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1: 74 percent / Ba(OH)2*8H2O / acetonitrile / 1 h / 60 °C 2: 32 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 7 h 3: 84 percent / H2; AcOH / Pd/C / 2 h / atmospheric pressure 4: 72 percent / H2SO4 / 19 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 74 percent / Ba(OH)2*8H2O / acetonitrile / 1 h / 60 °C 2: 32 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 6 h 3: 37 percent / H2SO4 / 26 h / Heating View Scheme |
The Resatorvid, with the CAS registry number 243984-11-4, is also known as UNII-H2MZ648C31. This chemical's molecular formula is C15H17ClFNO4S. Its IUPAC name is called ethyl (6R)-6-[(2-chloro-4-fluorophenyl)sulfamoyl]cyclohexene-1-carboxylate.
Physical properties of Resatorvid: (1)ACD/LogP: 3.02; (2)#H bond acceptors: 5; (3)#H bond donors: 1; (4)#Freely Rotating Bonds: 5; (5)Index of Refraction: 1.574; (6)Molar Refractivity: 85.313 cm3; (7)Molar Volume: 258.623 cm3; (8)Surface Tension: 52.008 dyne/cm; (9)Density: 1.399 g/cm3; (10)Flash Point: 233.184 °C; (11)Enthalpy of Vaporization: 72.292 kJ/mol; (12)Boiling Point: 461.958 °C at 760 mmHg; (13)Vapour Pressure: 0 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCOC(=O)C1=CCCCC1S(=O)(=O)NC2=C(C=C(C=C2)F)Cl
(2)Isomeric SMILES: CCOC(=O)C1=CCCC[C@H]1S(=O)(=O)NC2=C(C=C(C=C2)F)Cl
(3)InChI: InChI=1S/C15H17ClFNO4S/c1-2-22-15(19)11-5-3-4-6-14(11)23(20,21)18-13-8-7-10(17)9-12(13)16/h5,7-9,14,18H,2-4,6H2,1H3/t14-/m1/s1
(4)InChIKey: LEEIJTHMHDMWLJ-CQSZACIVSA-N