cis-Bicyclo[3.3.0]oct-2-ene

Base Information

• Chemical Name: cis-Bicyclo[3.3.0]oct-2-ene
• CAS No.: 930-99-4
• Molecular Formula: C8H12
• Molecular Weight: 108.183
• Hs Code.: 2912299000
• European Community (EC) Number: 213-228-2
• Nikkaji Number: J293.402G
• Mol file: 930-99-4.mol

Synonyms:930-99-4;cis-Bicyclo[3.3.0]oct-2-ene;cis-1,2,3,3a,4,6a-Hexahydropentalene;KEHFJHPSOFFXBO-SFYZADRCSA-N;AKOS006275636

Chemical Property of cis-Bicyclo[3.3.0]oct-2-ene

Chemical Property:

• Vapor Pressure: 8.415mmHg at 25°C
• Boiling Point: 138.3 °C at 760 mmHg
• Flash Point: 18.5 °C
• PSA: 0.00000
• Density: 0.93 g/cm³
• LogP: 2.36260
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 108.093900383
• Heavy Atom Count: 8
• Complexity: 113

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2CC=CC2C1
• Isomeric SMILES: C1C[C@@H]2CC=C[C@@H]2C1

Technology Process of cis-Bicyclo[3.3.0]oct-2-ene

There total 36 articles about cis-Bicyclo[3.3.0]oct-2-ene 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: 52.0%

cyclooctyne (1781-78-8) → bicyclo[3.3.0]oct-1(5)-ene (6491-93-6) + (3aS,6aS)-1,2,3,3a,4,6a-Hexahydro-pentalene (930-99-4)

Guidance literature:

cyclooctyne; With sodium sulfate; In chloroform; at 20 ℃; Schlenk technique; Molecular sieve;

With silver hexafluoroantimonate; chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); at 100 ℃; for 3h; Reagent/catalyst; Solvent; Molecular sieve; Sealed tube; Schlenk technique;

DOI:10.1002/ejic.201600021

Reference yield: 46.0%

1,5-cis,cis-cyclooctadiene (1552-12-1,111-78-4) → (3aS,6aS)-1,2,3,3a,4,6a-Hexahydro-pentalene (930-99-4) + dipotassium cyclooctatetraenide (34480-05-2)

Guidance literature:

1,5-cis,cis-cyclooctadiene; With Naphthalene anion ( K⁽¹⁺⁾ is the counterion); In n-heptane; for 17h; Heating;

In tetrahydrofuran; n-heptane; at 20 ℃; for 72h;

DOI:10.1016/S0040-4039(02)00144-2

Reference yield: 45.0%

1,5-cis,cis-cyclooctadiene (1552-12-1,111-78-4) → cis-Cyclooctene (931-88-4,931-87-3,25267-51-0) + (3aS,6aS)-1,2,3,3a,4,6a-Hexahydro-pentalene (930-99-4)

Guidance literature:

With hydrogen; sodium; magnesium oxide; at 249.9 ℃;

upstream raw materials:

(3aRS,6aSR)-hexahydro-2(1H)-pentalenone

(3a'R,6a'S)-5,5-dimethyltetrahydro-1'H-spiro[1,3-dioxane-2,2'-pentalen]-5'(3'H)-one

5,5-dimethylhexahydro-1'H-spiro[1,3-dioxane-2,2'-pentalene]

norbornene

Downstream raw materials:

(3aRS,6aSR)-hexahydro-2(1H)-pentalenone

N-<carbonyl>-cis-bicyclo<3.3.0>-3-oct-endo-2-enesulfinamide

cis-bicyclo[3.3.0]octan-2-one

(1bR,4aR)-Octahydro-1-oxa-cyclopropa[a]pentalene

Refernces

• 1、 Das, Animesh,Hua, Yuanda,Yousufuddin, Muhammed,Cundari, Thomas R.,Jeon, Junha,Dias, H.V. Rasika. "Gold-Mediated Isomerization of Cyclooctyne to Ring Fused Olefinic Bicycles". . p. 995 - 1001. Retrieved 2016/03/15.
• 2、 Simons, Leslie H.,Lagowski. "Cyclooctatetraene dianion from 1,5-cyclooctadiene. A synthesis in the presence of naphthalene radical anion". . p. 1771 - 1773. Retrieved 2007/10/03.