441619

(1S)-(+)-3-Caren

99%

• Synonym(e): (+)-3-Caren, (1S)-3,7,7-Trimethyl-bicyclo[4.1.0]hept-3-en
• Empirische Formel (Hill-System): C₁₀H₁₆
• CAS-Nummer: 498-15-7
• Molekulargewicht: 136.23
• Beilstein: 1902767
• EG-Nummer: 207-856-6
• MDL-Nummer: MFCD00066417
• UNSPSC-Code: 12352205
• PubChem Substanz-ID: 24867688
• NACRES: NA.22

Eigenschaften

• Assay: 99%
• Form: liquid
• Optische Aktivität: [α]20/D +17°, neat
• Brechungsindex: n20/D 1.472 (lit.)
• bp: 170-172 °C (lit.)
• Dichte: 0.865 g/mL at 25 °C (lit.)
• SMILES String: [H][C@@]12CC=C(C)C[C@]1([H])C2(C)C
• InChI: 1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9+/m1/s1
• InChIKey: BQOFWKZOCNGFEC-BDAKNGLRSA-N

Beschreibung

Allgemeine Beschreibung

(1S)-(+)-3-Carene is a monoterpene.

Anwendung

Chiral building block for the preparation of bicyclo[3.2.0]heptenes that are useful intermediates in the synthesis of (+)-lineatin and both enantiomers of capnellene. Has been converted to its corresponding allenyl allylic ether for studies of its thermal isomerization chemistry. Precursor to di(4-isocaranyl)borane, an asymmetric hydroboration reagent for olefins.

(1S)-(+)-3-Carene has been used as a standard during the quantification of components in Lavandula stoechas essential oils by fast gas chromatography-mass spectrometry (FGC-EI/MS). It may be used as a starting material in the total synthesis of (+)-ingenol. It may also be used to synthesize (1S,3S,4S,6R)-3,7,7-trimethyl-4-morpholino-4-yl-bicyclo(4.1.0)heptano-3-ol, which can catalyze the addition of diethylzinc to different aldehydes with high enantioselectivity.

Sicherheitshinweise

• Piktogramme: GHS02,GHS08,GHS07,GHS09
• Signalwort: Danger
• H-Sätze: H226,H304,H315,H317,H410
• P-Sätze: P210 - P273 - P280 - P301 + P310 - P303 + P361 + P353 - P331
• Gefahreneinstufungen: Aquatic Acute 1 - Aquatic Chronic 1 - Asp. Tox. 1 - Flam. Liq. 3 - Skin Irrit. 2 - Skin Sens. 1
• Lagerklassenschlüssel: 3 - Flammable liquids
• WGK: WGK 3
• Flammpunkt (°F): 116.6 °F - closed cup
• Flammpunkt (°C): 47 °C - closed cup
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter