4-(Trimethylsilyl)but-3-yn-2-ol
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Grundinformationen
- CAS
6999-19-5- Standard-SMILES
CC(O)C#C[Si](C)(C)C- InChIKey
HJJSDJHRTMFJLP-UHFFFAOYSA-N- Summenformel
- C7H14OSi
- Durchschnittliche Molmasse
- 142,274 g/mol
- Monoisotopische Masse
- 142,0813916
Namen und Bezeichner
- Bevorzugter Name
- 4-(Trimethylsilyl)but-3-yn-2-ol
- IUPAC
- 4-(Trimethylsilyl)but-3-yn-2-ol
- Englischer Name
- 4-Trimethylsilyl-3-butyn-2-ol
- Summenformel
- C7H14OSi
- Molmasse
- 142.27
Namen und Synonyme
DK369TIMTEC-BB SBB0090274-Trimethylsilyl-3-butyn-2-ol1-TRIMETHYLSILYLBUT-1-YNE-3-OL4-(Trimethysilyl)-3-butyn-2-ol4-Trimethylsilyl-3-butynol, t4-(triMethylsilyl)but-3-yn-2-ol3-Butyn-2-ol, 4-(trimethylsilyl)-4-TRIMETHYLSILYL-3-BUTYN-2-OL (+/-)(+/-) 4-TRIMETHYLSILYL-3-BUTYN-2-OL
Datenbank-Bezeichner
- CAS
6999-19-5- PubChem CID
- 2760828
- DTXSID
DTXSID00990235- EC Number
- 628-368-3
- Nikkaji
- J846.033G
Eigenschaften
Physikochemische Eigenschaften
- Siedepunkt
- 76 °C · 76 °C
- Dichte
- 0.847 g/mL · 0.847 g/mL at 25 °C
- Brechungsindex
- 20 · n 20/D 1.446
- Flammpunkt
- 143 °F · 143 °F
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- highly soluble in all standard organic solvents (hexanes, toluene, CH2Cl2, EtOAc, alcohols, ethers). Partially soluble in water.
- Aggregatzustand
- clear liquid
- pka
- 13.78 · 13.78±0.20(Predicted)
- Farbe
- Colorless to Light orange to Yellow
- Wichte
- 0.846 · 0.846
- BRN
- 1923632 · 1923632
- InChI
- InChI=1S/C7H14OSi/c1-7(8)5-6-9(2,3)4/h7-8H,1-4H3
- InChIKey
- HJJSDJHRTMFJLP-UHFFFAOYSA-N
- SMILES
- CC(O)C#C[Si](C)(C)C
- CAS Datenbank
- 6999 · 6999-19-5(CAS DataBase Reference)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- 3
- tsca
- No
- ridadr
- 1993
- hs_code
- 29319090
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26
- hazard_class
- 3
- packing_group
- III
- Speicherklasse
- 10 - Combustible liquids
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
Chemie und Industrie
Anwendungen
VerwendenMore recently, Mulzer has reported use of the corresponding allenylsilane derived from 4-TMS-3-butyn-2-ol for use in the synthesis of the C13–C18 fragment of branimycin (eq 2).
Darstellung
synthetischeracemic 4-trimethylsilyl-3-butyn-2-ol can be prepared by deprotonation with strong bases (BuLi, LDA, Grignards reagents) of trimethylsilylacetylene followed by addition to acetaldehyde.Deprotonation of 3-butyn-2- ol followed by quenching with excess trimethylsilyl chloride followed by concomitant hydrolysis of the trimethylsilyl ether is generally the most straightforward route.Enzymatic reduction of 4-TMS-3-butyn-2-one has also been used to prepare the reagent using alcohol dehydrogenase.Preparation of nonracemic 4-TMS-3-butyn-2-ol has been accomplished by asymmetric addition of dimethylzinc to acetaldehyde promoted by TADDOL or addition of a trimethylsilylvinylsulfoxide to acetaldehyde followed by thermal elimination of the sulfoxide.Asymmetric reduction of 4- TMS-3-butyn-2-one using stoichiometric reducing reagents, catalytic transfer hydrodrogenation,and enzymatic reduction with isolated protein or whole cells afford the 4-TMS-3-butyn- 2-ol with varying degrees of enantioenrichment.Enzymatic resolution by esterification of the racemic alcohol is the method of choice for the large-scale preparation.
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