498-15-7

Basic information

• Product Name: (1S)-(+)-3-Carene
• Synonyms: (1S)-(+)-car-3-ene;(1S)-3,7,7-TRIMETHYLBICYCLO[4.1.0]HEPT-3-ENE;(1S)-(+)-3-CARENE;(+)-3-CARENE;(+)-3-CARENE, TERPENE STANDARD;Bicyclo4.1.0hept-3-ene, 3,7,7-trimethyl-, (1S,6R)-;(+)-3-Carene, (1S)-3,7,7-Trimethylbicyclo[4.1.0]hept-3-ene;(1S,6R)-3-Carene
• CAS NO: 498-15-7
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23
• EINECS: 207-856-6
• Mol File: 498-15-7.mol
• Article Data: 8

Chemical Properties

• Melting Point: 25°C (estimate)
• Boiling Point: 170-172 °C(lit.)
• Flash Point: 131 °F
• Appearance: clear very slightly yellow/liquid (clear)
• Density: 0.865 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.86mmHg at 25°C
• Refractive Index: n20/D 1.473
• Storage Temp.: ?20°C
• Solubility: soluble in Acetone,Ethanol,Benzene
• Water Solubility: <0.1 g/100 mL at 22 C
• Merck: 14,1836
• BRN: 1902767
• CAS DataBase Reference: (1S)-(+)-3-Carene(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-(+)-3-Carene(498-15-7)
• EPA Substance Registry System: (1S)-(+)-3-Carene(498-15-7)

Safety Data

• Hazard Codes: Xi,N
• Statements: 10-50/53-43
• Safety Statements: 36/37-60-61
• RIDADR: UN 2319 3/PG 3
• WGK Germany: 2
• RTECS: FH8400000
• F: 10-23
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 498-15-7(Hazardous Substances Data)

Usage

Uses

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.

Definition

ChEBI: A car-3-ene (3,7,7-trimethylbicyclo[4.1.0]hept-3-ene) that has S configuration at position 1 and R configuration at position 6.

General Description

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

InChI:InChI=1/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9+/m1/s1

Upstream product

• 116872-39-0 (+/-)-10-phenylsulfonylcar-3-ene 
• 936-91-4 3-carene epoxide 
• 4497-92-1 2-carene 
• 917-54-4 methyllithium 
• 94806-25-4 (E)-4-(Tri-n-butylstannyl)-3-buten-2-one 
• 78-79-5 isoprene 
• 82470-87-9 α-terpinylphenylsulphide 
• 201230-82-2 carbon monoxide 

Downstream Products

• 140242-08-6 4-methyl-N-(3-caren-10-yl)benzenesulfonamide 
• 140242-07-5 (1S,2S,6R)-4-methyl-N-trans-(3-caren-2-yl)benzenesulfonamide 
• 5208-37-7 8-hydroxy-m-cymene 
• 5208-31-1 (5S)-(-)-5β-(1-Hydroxy-1-methylethyl)-1-methyl-1,3-cyclohexadien 
• 65221-02-5 3-caren-9-ol 
• 498-12-4 3-carene-10-carboxylic acid 
• 74496-72-3 3-carene-9-carboxylic acid 
• 74496-73-4 (-)-3-carene-9-carboxylic acid 
• 57457-02-0 cis-3α,4α-caranediol 
• 10395-46-7 1S,3R,4S,6R-(+)-3β,4β-caranediol 
• 22556-08-7 trans-3,4-caranediol 
• 22327-32-8 4,7,7-trimethylbicyclo[4.1.0]hept-3-en-2-one 
• 2767-18-2 3,6,6-trimethylcyclohepta-2,4-dien-1-one 
• 936-91-4 3-carene epoxide 

Relevant articles and documents

Regioselective and Stereospecific Copper-Catalyzed Deoxygenation of Epoxides to Alkenes

Two copper salts (Cu(CF3CO2)2 and IMesCuCl) were identified as earth-abundant, inexpensive, but effective metal catalysts together with diazo malonate for chemo-/regioselective and stereospecific deoxygenation of various epoxides with tolerance of common functional groups (alkene, ketone, ester, p-methoxybenzyl, benzyl, tert-butyldimethylsilyl, and triisopropylsilyl). In particular, the unprecedented regioselectivity allowed for the first time monodeoxygenation of diepoxides to alkenyl epoxides. Density functional theory mechanistic studies showed that the deoxygenation occurred by collapsing the free ylide, unfavoring the possible intuitive pathway via cycloreversion of possible oxetane.

Syntheses with organoboranes - VIII. Transformation of (1S,6R)-(+)-2- carene into (1S,6R)-(+)-3(10)-carene and (1R,5R)-(-)-α-thujene into (1R,5R)- (+)-sabinene

The transformation of (1S,6R)-(+)-2-carene and (1R,5R)-(-)-α-thujene into (1S,6R)-(+)-3(10)-carene and (1R,5R)-(+)-sabinene, respectively, by metallation-transmetallation-hydrolysis via the corresponding allylic organoborane intermediates is described.

Stereospecific Conversions of (+)-2- and (+)-3-Carenes into Optically active Seven-Membered Ring Systems

The reactions of (+)-2-carene (6b) and (+)-3-carene (15) with iron carbonyls are studied under various conditions.Besides double bond isomerization and interconversion of the two isomeric hydrocarbons, at least two different modes of ring opening leading to six- and seven-membered ring products are observed.Under mild conditions the primary ring opening complex 7b is isolated without loss of sterical information.Carbonylation of 7b under various conditions yields optically active cycloheptene systems 18, 19, and 20 or the bicyclic systems 9b and 10b.