(1S)-(+)-3-Carene

Base Information

• Chemical Name: (1S)-(+)-3-Carene
• CAS No.: 498-15-7
• Molecular Formula: C10H16
• Molecular Weight: 136.237
• European Community (EC) Number: 207-856-6
• Nikkaji Number: J2.417.458A
• Mol file: 498-15-7.mol

Synonyms:(1S)-(+)-3-Carene;(1S)-3,7,7-Trimethylbicyclo(4.1.0)hept-3-ene;(S)-(+)-3-Carene;(1S)-3,7,7-trimethylbicyclo[4.1.0]hept-3-ene;(+)-3-delta-Carene;BQOFWKZOCNGFEC-GKAPJAKFSA-N;AKOS015890254

Chemical Property of (1S)-(+)-3-Carene

Chemical Property:

• Vapor Pressure: 1.86mmHg at 25°C
• Melting Point: 25°C (estimate)
• Refractive Index: n20/D 1.473
• Boiling Point: 170-172 ºC
• Flash Point: 55 ºC
• PSA: 0.00000
• Density: 0.865
• LogP: 2.99870
• Storage Temp.: ?20°C
• Solubility.: soluble in Acetone,Ethanol,Benzene
• Water Solubility.: <0.1 g/100 mL at 22 C
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 136.125200510
• Heavy Atom Count: 10
• Complexity: 186

Purity/Quality:

99.9% ^*data from raw suppliers

(1S)-(+)-3-Carene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,N
• Statements: 10-50/53-43
• Safety Statements: 36/37-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Terpenes
• Canonical SMILES: CC1=CCC2C(C1)C2(C)C
• Isomeric SMILES: CC1=CCC2[C@H](C1)C2(C)C
• 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.

Technology Process of (1S)-(+)-3-Carene

There total 13 articles about (1S)-(+)-3-Carene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

C30H45BO → (+)-Δ3-carene (498-15-7,19079-29-9) + (S)-1-Phenyl-3-buten-1-ol (77118-87-7,936-58-3)

Guidance literature:

With boron trifluoride diethyl etherate; isobutyraldehyde; at 65 ℃; for 48h;

DOI:10.1021/jo00050a044

Reference yield: 76.5%

(+/-)-10-phenylsulfonylcar-3-ene (116872-39-0) → Δ3-carene (498-15-7,13466-78-9,20296-50-8,116783-27-8,19079-29-9)

Guidance literature:

With ammonia; lithium; In diethyl ether; at -50 ℃; for 1h;

DOI:10.1007/BF01455479

Reference yield: 65.0%

3-carene epoxide (936-91-4) → (+)-Δ3-carene (498-15-7,19079-29-9)

Guidance literature:

With dimethyl diazomalonate; chloro[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene]copper(I); In toluene; for 4h; Reagent/catalyst; stereospecific reaction; Sealed tube; Reflux;

DOI:10.1021/acs.orglett.6b02405

upstream raw materials:

2-carene

carbon monoxide

α-terpinylphenylsulphide

methyllithium

Downstream raw materials:

m-mentha-1,3(8)-diene

4-isocaranol

2-carene

(-)-(1R,3R,6S)-4-methylene-7,7-dimethylbicyclo[4.1.0]heptan-3-ol

Refernces

• 1、 Il'Ina, Irina V.,Volcho, Konstantin P.,Korchagina, Dina V.,Salnikov, Georgi E.,Genaev, Alexander M.,Karpova, Elena V.,Salakhutdinov, Nariman F.. "Unusual reactions of (+)-Car-2-ene and (+)-Car-3-ene with aldehydes on K10 clay". experimental part. p. 2135 - 2150. Retrieved 2011/02/16.
• 2、 Brown, Herbert C.,Racherla, Uday S.,Liao, Y.,Khanna, Vijay V.. "Chiral Synthesis via Organoboranes. 35. Simple Procedures for the Efficient Recycling of the Terpenyl Chiral Auxiliaries and Convenient Isolation of the Homoallylic Alcohols in Asymmetric Allyl- and Crotylboration of Aldehydes". . p. 6608 - 6614. Retrieved 2007/10/02.