2a,4a,6a,6b-tetrahydrocyclopenta[cd]pentalene

Base Information

• Chemical Name: 2a,4a,6a,6b-tetrahydrocyclopenta[cd]pentalene
• CAS No.: 6053-74-3
• Molecular Formula: C10H10
• Molecular Weight: 130.1864
• Mol file: 6053-74-3.mol

Synonyms:Triquinacen;

Chemical Property of 2a,4a,6a,6b-tetrahydrocyclopenta[cd]pentalene

Chemical Property:

• Vapor Pressure: 0.686mmHg at 25°C
• Melting Point: 20 °C
• Boiling Point: 192.3°Cat760mmHg
• Flash Point: 46.5°C
• PSA: 0.00000
• Density: 1.091g/cm³
• LogP: 2.16060

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2a,4a,6a,6b-tetrahydrocyclopenta[cd]pentalene

There total 33 articles about 2a,4a,6a,6b-tetrahydrocyclopenta[cd]pentalene 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: 80.0%

(2aR,3S,4aS,6R,6aS,6bR)-Decahydro-cyclopenta[cd]pentalene-1,3,6-triol (78168-46-4,102130-88-1,119241-54-2,119241-55-3) → All-cis-tricyclo(5.2.1.04,10and)deca-2,5,8-trien (6053-74-3)

Guidance literature:

In N,N,N,N,N,N-hexamethylphosphoric triamide; for 48h; Yields of byproduct given; Heating;

DOI:10.1021/ja00188a035

Reference yield: 63.8%

cis-3,5,8-tris(mesyloxy)tricyclo<5.2.1.04,10>decane → All-cis-tricyclo(5.2.1.04,10and)deca-2,5,8-trien (6053-74-3) + isotriquinacene (89032-66-6)

Guidance literature:

With aluminum oxide; In dichloromethane; for 10h; Ambient temperature;

DOI:10.1021/ja00188a035

Reference yield:

Phosphoric acid diethyl ester (2aS,4aR,6aS,6bR)-6-(tetrahydro-pyran-2-yloxy)-2a,4a,5,6,6a,6b-hexahydro-cyclopenta[cd]pentalen-1-yl ester → All-cis-tricyclo(5.2.1.04,10and)deca-2,5,8-trien (6053-74-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) lithium / 1.) liquid ammonia

3: activated alumina

With aluminum oxide; lithium;

DOI:10.1021/ja00286a029

upstream raw materials:

pentacyclo<3.3.2.0^2,4.0^3,7.0^6,8>dec-9-ene

hexacyclo[4.4.0.0^2,4.0^3,9.0^5,7.0^8,10]decane

tert.-butyl lithium

1-Bromtriquinacen

Downstream raw materials:

Barettan

Refernces

• 1、 Paquette, Leo A.,Kramer, James D.. "Isotriquinacene". . p. 1445 - 1446. Retrieved 1984.
• 2、 Verevkin, Sergei P.,Kuemmerlin, Martin,Hickl, Ernst,Beckhaus, Hans-Dieter,Ruechardt, Christoph,Kozhushkov, Sergei I.,Haag, Rainer,Boese, Roland,Benet-Bucholz, Jordi,Nordhoff, Karsten,De Meijere, Armin. "Thermochemical and x-ray crystallographic investigations of some (CH)10 hydrocarbons: Basketene, Nenitzescu's hydrocarbon, and snoutene". . p. 2280 - 2287. Retrieved 2007/10/03.
• 3、 Gupta, Ashok K.,Fu, Xiaoyong,Snydert, James P.,Cook, James M.. "General approach for the synthesis of polyquinenes via the Weiss reaction". . p. 3665 - 3710. Retrieved 2007/10/02.