| 词条 | Mosher's acid |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 428793132 | Name = Mosher's acid | ImageFileR1 = (R)-Mosher Acid Formula V.1.svg | ImageName = | ImageFileL1 = (S)-Mosher Acid Formula V.1.svg | ImageFileR2 = R-Mosher's-acid-3D-balls.png | ImageFileL2 = S-Mosher's-acid-3D-balls.png | IUPACName =(R)-3,3,3-trifluoro-2- (S)-3,3,3-trifluoro-2- | OtherNames = Methoxy(trifluoromethyl)phenylacetic acid, MTPA |Section1={{Chembox Identifiers | SMILES = COC(C(O)=O)(c1ccccc1)C(F)(F)F | CASNo_Ref = {{cascite|correct|??}} | CASNo = 81655-41-6 | CASNo_Comment = (racemic) | CASNo2_Ref = {{cascite|changed|??}} | CASNo2 = 20445-31-2 | CASNo2_Comment = (R) | CASNo3_Ref = {{cascite|changed|??}} | CASNo3 = 17257-71-5 | CASNo3_Comment = (S) | RTECS = | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 78043 | InChI = 1/C10H9F3O3/c1-16-9(8(14)15,10(11,12)13)7-5-3-2-4-6-7/h2-6H,1H3,(H,14,15) | InChIKey = JJYKJUXBWFATTE-UHFFFAOYAJ | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C10H9F3O3/c1-16-9(8(14)15,10(11,12)13)7-5-3-2-4-6-7/h2-6H,1H3,(H,14,15) | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = JJYKJUXBWFATTE-UHFFFAOYSA-N |Section2={{Chembox Properties | Formula = C10H9F3O3 | MolarMass = 234.17 | Appearance = solid | Density = | Solubility = | MeltingPtC = 46 to 49 | MeltingPt_notes = | BoilingPtC = 105 to 107 | BoilingPt_notes = at 1 torr | pKa = | pKb = | Viscosity = |Section3={{Chembox Structure | Dipole = |Section7={{Chembox Hazards | ExternalSDS = | MainHazards = | FlashPtC = 110 | RPhrases = {{R36/37/38}} | SPhrases = {{S26}}/{{S36}} |Section8={{Chembox Related | OtherFunction_label = acyl chloride | OtherFunction = Mosher's acid chloride | OtherCompounds = }} Mosher's acid, or α-methoxy-α-trifluoromethylphenylacetic acid (MTPA) is a carboxylic acid which was first used by Harry Stone Mosher as a chiral derivatizing agent.[1][2][3][4] It is a chiral molecule, consisting of R and S enantiomers. ApplicationsAs a chiral derivatizing agent, it reacts with an alcohol or amine[5] of unknown stereochemistry to form an ester or amide. The absolute configuration of the ester or amide is then determined by proton and/or 19F NMR spectroscopy. Mosher's acid chloride, the acid chloride form, is sometimes used because it has better reactivity.[6]See also
References1. ^{{cite journal|author1=J. A. Dale |author2=D. L. Dull |author3=H. S. Mosher | title = α-Methoxy-α-trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines| journal = Journal of Organic Chemistry| year = 1969| volume = 34| issue = 9| pages = 2543–2549| doi = 10.1021/jo01261a013}} 2. ^{{cite journal|author1=J. A. Dale |author2=H. S. Mosher | title = Nuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α-trifluoromethylphenylacetate (MTPA) esters| journal = Journal of the American Chemical Society| year = 1973| volume = 95| issue = 2| pages = 512–519| doi = 10.1021/ja00783a034}} 3. ^{{cite journal|author1=Y. Goldberg |author2=H. Alper | title = A new and simple synthesis of Mosher's acid| journal = Journal of Organic Chemistry| year = 1992| volume = 57| issue = 13| pages = 3731–3732| doi = 10.1021/jo00039a043}} 4. ^{{cite journal|author1=D. L. Dull |author2=H. S. Mosher | title = Aberrant rotatory dispersion curves of α-hydroxy- and α-methoxy-α-trifluoromethylphenylacetic acids| journal = Journal of the American Chemical Society| year = 1967| volume = 89| issue = 16| pages = 4230–4230| doi = 10.1021/ja00992a053}} 5. ^See for example: Mosher Amides: Determining the Absolute Stereochemistry of Optically-Active Amines Allen, Damian A.; Tomaso, Anthony E., Jr.; Priest, Owen P.; Hindson, David F.; Hurlburt, Jamie L. J. Chem. Educ. 2008, 85, 698. Abstract 6. ^{{cite journal|author1=D. E. Ward |author2=C. K. Rhee | title = A simple method for the microscale preparation of Mosher's acid chloride| journal = Tetrahedron Letters| year = 1991| volume = 32| issue = 49| pages = 7165–7166| doi = 10.1016/0040-4039(91)80466-J}} 4 : Stereochemistry|Carboxylic acids|Trifluoromethyl compounds|Phenyl compounds |
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