| Revision as of 13:29, 11 November 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI->StdInChI InChI1->InChI SMILES.← Previous edit |
Latest revision as of 17:44, 17 September 2024 edit undoCitation bot (talk | contribs)Bots5,459,887 edits Removed parameters. | Use this bot. Report bugs. | Suggested by Neko-chan | Category:CS1 maint: DOI inactive as of February 2024 | #UCB_Category 22/293 |
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| verifiedrevid = 340121275 |
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| verifiedrevid = 460015608 |
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| ImageFile = 10-camphorsulfonic acid.svg |
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| ImageFileL1 = 10-camphorsulfonic acid.svg |
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| ImageSize = 100px |
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| ImageSizeL1 = 100px |
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| ImageName = Wireframe model of camphorsulfonic acid |
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| ImageNameL1 = Wireframe model of camphorsulfonic acid |
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| ImageFileR1 = Camphorsulfonic-acid-from-xtal-3D-bs-17-view-5.png |
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| PIN = 4,7,7-Trimethyl-3-oxo-norbornane-2-sulfonic acid |
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| ImageSizeR1 = 125px |
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| SystematicName = {7,7-Dimethyl-2-oxobicycloheptan-1-yl}methanesulfonic acid |
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| PIN = (7,7-dimethyl-2-oxobicycloheptan-1-yl)methanesulfonic acid |
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| OtherNames = Reychler's acid |
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| OtherNames = Reychler's acid; 2-Oxobornane-10-sulfonic acid |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 5872-08-2 |
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| CASNo_Ref = {{Cascite|correct|??}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo1 = 35963-20-3 |
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| CASNo = 5872-08-2 |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| CASNo1_Comment = (1''R'') |
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| CASNo1 = 35963-20-3 |
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| CASNo1_Ref = {{Cascite|correct|??}} |
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| CASNo1_Comment = (1''R'') |
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| PubChem = 18462 |
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| PubChem_Ref = {{Pubchemcite|correct|PubChem}} |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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| PubChem1 = 131278 |
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| CASNo2 = 3144-16-9 |
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| PubChem1_Comment = (1''R'') |
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| CASNo2_Comment = (1''S'') |
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| PubChem1_Ref = {{Pubchemcite|correct|PubChem}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem2 = 218580 |
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| UNII = D8D049375Q |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| PubChem2_Comment = (1''S'') |
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| UNII1 = Y6075I4FXE |
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| PubChem2_Ref = {{Pubchemcite|correct|PubChem}} |
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| UNII1_Comment = (1''R'') |
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| PubChem3 = 43833349 |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| PubChem3_Comment = (4''R'') |
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| UNII2 = 9TLZ01S15L |
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| PubChem3_Ref = {{Pubchemcite|correct|PubChem}} |
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| UNII2_Comment = (1''S'') |
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| PubChem4 = 3057042 |
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| PubChem4_Comment = (4''S'') |
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| PubChem = 18462 |
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| PubChem4_Ref = {{Pubchemcite|correct|PubChem}} |
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| ChemSpiderID = 17438 |
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| PubChem1 = 131278 |
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| PubChem1_Comment = (1''R'') |
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| ChemSpiderID_Ref = {{Chemspidercite|correct|ChemSpider}} |
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| PubChem2 = 218580 |
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| ChemSpiderID1 = 116050 |
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| ChemSpiderID1_Comment = (1''R'') |
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| PubChem2_Comment = (1''S'') |
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| PubChem3 = 43833349 |
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| ChemSpiderID1_Ref = {{Chemspidercite|correct|ChemSpider}} |
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| PubChem3_Comment = (4''R'') |
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| ChemSpiderID2 = 189449 |
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| PubChem4 = 3057042 |
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| ChemSpiderID2_Comment = (1''S'') |
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| PubChem4_Comment = (4''S'') |
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| ChemSpiderID2_Ref = {{Chemspidercite|correct|ChemSpider}} |
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| ChemSpiderID = 17438 |
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| ChemSpiderID3 = 2318313 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID3_Comment = (4''S'') |
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| ChemSpiderID1 = 116050 |
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| ChemSpiderID3_Ref = {{Chemspidercite|correct|ChemSpider}} |
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| ChemSpiderID1_Comment = (1''R'') |
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| EINECS = 227-527-0 |
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| ChemSpiderID1_Ref = {{chemspidercite|correct|ChemSpider}} |
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| UNNumber = 1759 |
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| ChemSpiderID2 = 189449 |
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| MeSHName = 10-Camphorsulfonic+acid |
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| ChemSpiderID2_Comment = (1''S'') |
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| ChEBI = 55379 |
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| ChemSpiderID2_Ref = {{chemspidercite|correct|ChemSpider}} |
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| SMILES = CC1(C2CCC1(C(=O)C2)CS(=O)(=O)O)C |
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| ChemSpiderID3 = 2318313 |
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| SMILES1 = O=S(=O)(O)CC12C(=O)CC(CC1)C2(C)C |
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| ChemSpiderID3_Comment = (4''S'') |
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| StdInChI = 1S/C10H16O4S/c1-9(2)7-3-4-10(9,8(11)5-7)6-15(12,13)14/h7H,3-6H2,1-2H3,(H,12,13,14) |
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| ChemSpiderID3_Ref = {{chemspidercite|correct|ChemSpider}} |
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| StdInChI1 = 1/C10H16O4S/c1-9(2)7-3-4-10(9,8(11)5-7)6-15(12,13)14/h7H,3-6H2,1-2H3,(H,12,13,14) |
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| EINECS = 227-527-0 |
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| StdInChIKey = MIOPJNTWMNEORI-UHFFFAOYSA-N |
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| UNNumber = 1759 |
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| StdInChIKey = MIOPJNTWMNEORI-UHFFFAOYAN |
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| MeSHName = 10-Camphorsulfonic+acid |
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| Beilstein = 2216194}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| Section2 = {{Chembox Properties |
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| ChEBI = 55379 |
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| C = 10 | H = 16 | O = 4 | S = 1 |
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| SMILES = CC1(C2CCC1(C(=O)C2)CS(=O)(=O)O)C |
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| Appearance = |
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| SMILES1 = O=S(=O)(O)CC12C(=O)CC(CC1)C2(C)C |
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| Density = |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| MeltingPt = |
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| StdInChI = 1S/C10H16O4S/c1-9(2)7-3-4-10(9,8(11)5-7)6-15(12,13)14/h7H,3-6H2,1-2H3,(H,12,13,14) |
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| BoilingPt = |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| Solubility = |
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| StdInChIKey = MIOPJNTWMNEORI-UHFFFAOYSA-N |
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| pKa = 1.2 |
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}} |
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| Beilstein = 2216194 |
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| Section3 = {{Chembox Hazards |
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}} |
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| ExternalMSDS = |
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|Section2={{Chembox Properties |
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| FlashPt = |
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| C=10 | H=16 | O=4 | S=1 |
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| Autoignition = |
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| Appearance = |
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}} |
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| Density = |
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| MeltingPt = 195 °C (decomposes) |
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| BoilingPt = |
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| Solubility = |
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| pKa = 1.2 |
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}} |
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|Section3={{Chembox Hazards |
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| ExternalSDS = |
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| FlashPt = |
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| AutoignitionPt = |
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}} |
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}} |
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}} |
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'''Camphorsulfonic acid''', sometimes abbreviated '''CSA''' or '''10-CSA''' is a ]. Like typical ]s, it is a relatively strong acid that exists as a colourless solid that is soluble in organic solvents. |
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'''Camphorsulfonic acid''', sometimes abbreviated '''CSA''' or '''10-CSA''' is an ]. Like typical ]s, it is a relatively strong acid that is a colorless solid at room temperature and is soluble in water and a wide variety of organic substances. |
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This compound is commercially available. It can be prepared by sulfonation ] with ] and ]:<ref>{{OrgSynth | title = D,L-10-Camphorsulfonic acid (Reychler's Acid) | author = Paul D. Bartlett and L. H. Knox | prep = cv5p0194 | year = 1973 | collvol = 5 | collvolpages = 194}}</ref> |
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:] |
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This compound is commercially available. It can be prepared by sulfonation of ] with ] and ]:<ref>{{OrgSynth | title = D,L-10-Camphorsulfonic acid (Reychler's Acid) | first1 = Paul D.| last1= Bartlett | first2= L. H.| last2= Knox | doi = 10.15227/orgsyn.045.0012 | year = 1965 | volume = 45 | pages = 12}}</ref> |
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:] |
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Although this reaction appears to be a sulfonation of an unactivated methyl group, the actual mechanism is believed to involve a retro-], deprotonation next to the tertiary carbocation to form an alkene, sulfonation of the alkene intermediate, and finally, semipinacol rearrangement to re-establish the ketone function.<ref>{{Cite book|title=Advanced organic chemistry : reaction mechanisms|last=Brückner|first=Reinhard|date=2002|publisher=Harcourt/Academic Press |isbn= 9780080498805 |location= San Diego |oclc=269472848}}</ref> |
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In ], CSA and its derivatives can be used as ]s for chiral amines and other cations.<ref>{{cite journal | journal = Heterocycles | volume = 31 | pages = 353 | year = 1990 | doi = 10.3987/COM-89-5250 | title = Preparation of Enatiomerically Pure Decahydro-6H-isoquinonaphthyridines Utilizing the Openshaw-Whittaker Hexahydrobenzoquinolizinone Resolution | last1 = Clark | first1 = Robin D. | last2 = Kern | first2 = John R. | last3 = Kurz | first3 = Lilia J. | last4 = Nelson | first4 = Janis T. | issue = 2| doi-access = free }}</ref><ref>{{cite encyclopedia| first1= André B.| last1= Charette |title= 3-Bromocamphor-8-sulfonic Acid| encyclopedia= Encyclopedia of Reagents for Organic Synthesis |year= 2001| publisher= John Wiley & Sons| doi= 10.1002/047084289X.rb283| isbn= 0471936235}}</ref> The synthesis of ] was an example of this. 3-bromocamphor-8-sulfonic acid was used in the synthesis of enantiopure ].<ref>{{cite journal | journal = ] | doi = 10.1021/jo00381a052 | title = Crystallization-induced asymmetric transformation: Stereospecific synthesis of a potent peripheral CCK antagonist | year = 1987 | last1 = Reider | first1 = Paul J. | last2 = Davis | first2 = Paul | last3 = Hughes | first3 = David L. | last4 = Grabowski | first4 = Edward J. J. | volume = 52 | issue = 5 | pages = 955–957}}</ref> |
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Camphorsulfonic acid is also being used for the synthesis of ].<ref>{{cite journal | journal = ] | doi = 10.1002/ejoc.201900325 | title = Microwave-Assisted Metal-Free Rapid Synthesis of C4-Arylated Quinolines via Povarov Type Multicomponent Reactiont | year = 2019 | last1 = Chandra | first1 = Devesh | last2 = Dhiman | first2 = Ankit K | last3 = Kumar | first3 = Rakesh | last4 = Sharma | first4 = Upendra | volume = 2019 | issue = 16 | pages = 2753–2758| s2cid = 107383202 }}</ref> Camphorsulfonic acid is used in some pharmaceutical formulations, where is it referred to as '''camsilate''' or '''camsylate''', including ] and ]. Some studies (c.f. Lednicer) support that D-CSA was used for the resolution of ]. |
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A related derivative is 3-bromocamphor-8-sulfonic acid. Both sulfonic acids are useful ]s (as their sulfonate salts) for chiral amines and other cations.<ref>André B. Charette "3-Bromocamphor-8-sulfonic Acid" Encyclopedia of Reagents for Organic Synthesis 2001, John Wiley & Sons. {{DOI|10.1002/047084289X.rb283}}</ref> |
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==References== |
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==References== |
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{{reflist}} |
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<References/> |
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