Bicyclo[6.1.0]non-4-ene

Base Information

• Chemical Name: Bicyclo[6.1.0]non-4-ene
• CAS No.: 4729-13-9
• Molecular Formula: C9H14
• Molecular Weight: 122.20700
• Mol file: 4729-13-9.mol

Synonyms:cis-Bicyclo<6.1.0>non-4-en;Bicyclo<6.1.0>nonen-4;Bicyclo<6.1.0>non-4-en;bicyclo<6.1.0>non-4-ene;

Chemical Property of Bicyclo[6.1.0]non-4-ene

Chemical Property:

• PSA: 0.00000
• LogP: 2.75270

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Bicyclo[6.1.0]non-4-ene

There total 6 articles about Bicyclo[6.1.0]non-4-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: 75.0%

9,9-dichlorobicyclo<6.1.0>non-4-ene (4729-12-8) → cis-Bicyclo<6.1.0>non-4-en (4729-13-9)

Guidance literature:

With lithium; tert-butyl alcohol; In diethyl ether; for 2h; Heating;

Reference yield:

1,5-cis,cis-cyclooctadiene (1552-12-1,111-78-4) → cis-Bicyclo<6.1.0>non-4-en (4729-13-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide; benzyltriethylammonium chloride / hexane / 10 - 20 °C

2: lithium / 2-methyl-propan-2-ol

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; lithium; In hexane; tert-butyl alcohol; 1: Cycloaddition / 2: Dehalogenation;

DOI:10.1007/BF02494639

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + 1,5-cis,cis-cyclooctadiene (1552-12-1,111-78-4) → cis-Bicyclo<6.1.0>non-4-en (4729-13-9) + trans-tricyclo<7.1.0.04,6>decane (286-73-7,89955-58-8,89955-59-9) + cis-tricyclo<7.1.0.04,6>decane (286-73-7,89955-58-8,89955-59-9)

Guidance literature:

With bis(benzonitrile)palladium(II) dichloride; In dichloromethane; at -10 - 0 ℃; Product distribution; reactants ratio dependence;

DOI:10.1007/BF00995691

upstream raw materials:

diazomethane

1,5-cis,cis-cyclooctadiene

9,9-dichlorobicyclo<6.1.0>non-4-ene

Downstream raw materials:

hexahydro-indan-1-one

5-Methylcyclooctanon

5,6,7,8-Tetraphenyltricyclo<10.1.0.0^4,9>trideca-4,6,8-trien

Refernces

• 1、 Pinazzi et al.. "". . p. 45,53. Retrieved 1973.
• 2、 Kuznetsova,Kokoreva,Averina,Zefirov,Grishin,Zefirov. "Dehydrohalogenation of adducts of dichlorocarbene with cyclooctene and its peripherally cyclopropanated analogs". . p. 929 - 933. Retrieved 2007/10/03.
• 3、 Lukin, K. A.,Zefirov, N. S.. "REACTION OF CYCLIC OLEFINS CONTAINING CYCLOPROPANE FRAGMENTS WITH DIAZOMETHANE IN THE PRESENCE OF PALLADIUM(II) ACETATE". . p. 1487 - 1490. Retrieved 2007/10/02.