(-)-trans-Pinane

Base Information

• Chemical Name: (-)-trans-Pinane
• CAS No.: 10281-53-5
• Molecular Formula: C10H18
• Molecular Weight: 138.253
• Hs Code.: 2902199090
• European Community (EC) Number: 800-188-1,233-629-6
• UNII: 6603788013,26MVP5V1AP
• DSSTox Substance ID: DTXSID30858758,DTXSID801037317
• Nikkaji Number: J236.740H
• Wikidata: Q81986178
• ChEMBL ID: CHEMBL3109298
• Mol file: 10281-53-5.mol

Synonyms:(-)-cis-pinane;(1alpha,2alpha,5alpha)-isomer of pinane;pinane;pinane, (1alpha,3beta,5alpha)-(cis)-isomer;pinane, (1R-(1alpha,2beta,5alpha))-isomer;pinane, (1S-(1alpha,2beta,5alpha))-((-)-cis)-isomer;pinane, cis-;pinane, cis-(+)-;pinane, cis-(-)-;pinane, trans-

Chemical Property of (-)-trans-Pinane

Chemical Property:

• Vapor Pressure: 3.626mmHg at 25°C
• Melting Point: -53oC
• Refractive Index: n20/D 1.461
• Boiling Point: 157°Cat760mmHg
• Flash Point: 36°C
• PSA: 0.00000
• Density: 0.844g/cm³
• LogP: 3.07860
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 138.140850574
• Heavy Atom Count: 10
• Complexity: 146

Purity/Quality:

98%,99%, ^*data from raw suppliers

(1S)-(?)-trans-Pinane analytical standard ^*data from reagent suppliers

Safty Information:

• Statements: 10
• Safety Statements: 16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC2CC1C2(C)C
• Isomeric SMILES: C[C@H]1CC[C@H]2C[C@@H]1C2(C)C

Technology Process of (-)-trans-Pinane

There total 63 articles about (-)-trans-Pinane 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: 99.6%

Pinene (80-56-8,177698-18-9,25766-18-1) → pinane (4755-33-3,4795-86-2,4863-59-6,6876-13-7,10281-53-5,33626-25-4,112456-46-9,112456-47-0,473-55-2)

Guidance literature:

With hydrogen; at 130 ℃; Reagent/catalyst;

DOI:10.1134/S1070363219100013

Reference yield: 95.0%

Beta-pinene (177698-19-0,25719-60-2) → pinane (4755-33-3,4795-86-2,4863-59-6,6876-13-7,10281-53-5,33626-25-4,112456-46-9,112456-47-0,473-55-2)

Guidance literature:

With nickel(II) bis(octanoate); hydrogen; 1,4-bis(2,6-diisopropylphenyl)-2,3-dimethyl-1,4-diazabuta-1,3-diene; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In benzene-d6; at 50 ℃; for 12h; under 3040.2 Torr;

DOI:10.1021/acscatal.7b03909

Reference yield: 11.0%

Pinene (80-56-8,177698-18-9,25766-18-1) → pinane (4755-33-3,4795-86-2,4863-59-6,6876-13-7,10281-53-5,33626-25-4,112456-46-9,112456-47-0,473-55-2) + Isopinocampheol (27779-29-9) + (2S,3R)-2,6,6-Trimethyl-bicyclo[3.1.1]heptan-3-ol

Guidance literature:

With benzyltriethylammonium borohydride; chloro-trimethyl-silane; In dichloromethane; at 0 ℃; for 3h; Yields of byproduct given;

DOI:10.1039/c39890000903

upstream raw materials:

beta-pinene

(+)-α-pinene

(+)-pinocamphone

(1R,2R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one

Downstream raw materials:

1,1,2,3-tetramethylcyclohexane

2-methylisopropylbenzene

4-methylisopropylbenzene

1,2,4,5-tetramethylbenzene

Refernces

• 1、 Nebykov,Popov, Yu. V.,Mokhov,Latyshova,Shcherbakova,Nemtseva,Shishkin. "Colloid and Nanosized Catalysts in Organic Synthesis: XXII. Hydrogenation of Cycloolefins Catalyzed by Immobilized Transition Metals Nanoparticles in a Three-Phase System". . p. 1985 - 1989. Retrieved 2019.
• 2、 Cocker,W. et al.. "-". . p. 41 - 47. Retrieved 1966.
• 3、 Chapuis, Christian,Barthe, Michel,Muller, Bernard L.,Schulte-Elte, Karl H.. "Preparation and Absolute Configuration of (-)-(E)-α-trans-Bergamotenone". . p. 153 - 162. Retrieved 1998.
• 4、 Barros, Humberto J. V.,Ospina, Maria L.,Arguello, Eduardo,Rocha, William R.,Gusevskaya, Elena V.,Santos, Eduardo N. dos. "Rhodium catalyzed hydroformylation of β-pinene and camphene: effect of phosphorous ligands and reaction conditions on stereoselectivity". . p. 150 - 157. Retrieved 2003.
• 5、 Hu, Shunyou,Wang, Linlin,Chen, Xiaopeng,Wei, Xiaojie,Tong, Zhangfa,Yin, Lijiang. "The conversion of α-pinene to: Cis-pinane using a nickel catalyst supported on a discarded fluid catalytic cracking catalyst with an ionic liquid layer". . p. 5978 - 5986. Retrieved 2019.
• 6、 Lin, Yingrui,Ma, Dawei,Lu, Xiyan. "SELECTIVE CONVERSION OF PINANE INTO β-PINENE CATALYZED BY AN IRIDIUM PENTAHYDRIDE COMPLEX". . p. 407 - 410. Retrieved 1987.
• 7、 Li, Kaoxue,Wang, Kang,Liu, Chuanchao,Yang, Xuhao,Chen, Xia,Ren, Yang,Cao, Shuhua,Liu, Meifang,Tai, Xishi,Li, Fahui. "Efficient and selective reduction of α-pinene to cis-pinane by NaBH4 using NiCl2?6H2O/PEG-800/ethanol as the catalytic system". . p. 672 - 678. Retrieved 2019.
• 8、 Fischli, Albert,Mueller, Peter Michael. "Cob(I)alamin als Katalysator. Retention der Konfiguration bei der reduktiv-protonenuebertragenden Spaltung der Co,C-Bindung eines Alkylcobalamins". . p. 1619 - 1627. Retrieved 1980.
• 9、 Jenke, Thomas,Suess-Fink, Georg. "Kinetische Enantiomerendifferenzierung bei der katalytischen Hydrierung nicht funktionalisierter Terpenolefine mit chiral modifizierten Rutheniumclustern". . p. 383 - 391. Retrieved 1991.
• 10、 Dembitskii,A.D. et al.. "". . . Retrieved 1979.