Tricyclo[3.3.2.02,8]deca-6,9-dien-3-one

Base Information

• Chemical Name: Tricyclo[3.3.2.02,8]deca-6,9-dien-3-one
• CAS No.: 15719-09-2
• Molecular Formula: C₁₀H₁₀O
• Molecular Weight: 146.189
• Mol file: 15719-09-2.mol

Synonyms:Bullvalone

Chemical Property of Tricyclo[3.3.2.02,8]deca-6,9-dien-3-one

Chemical Property:

• Boiling Point: 265.1±9.0 °C(Predicted)
• PSA: 17.07000
• Density: 1.193±0.06 g/cm3(Predicted)
• LogP: 1.56360

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Tricyclo[3.3.2.02,8]deca-6,9-dien-3-one

There total 8 articles about Tricyclo[3.3.2.02,8]deca-6,9-dien-3-one 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: 37.0%

tricyclo<3.3.1.02,8>nona-3,6-dien-9-one (6006-24-2) + diazomethyl-trimethyl-silane (18107-18-1) → tricyclo[3.3.2.02,8]deca-6,9-dien-4-one (15719-09-2)

Guidance literature:

tricyclo<3.3.1.0^2,8>nona-3,6-dien-9-one; With n-butyllithium; In diethyl ether; at -78 ℃; Inert atmosphere; Schlenk technique;

diazomethyl-trimethyl-silane; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.5h; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201606101

Reference yield:

bicyclo[4.2.1]nona-2,4,7-trien-9-one (34733-74-9) → tricyclo[3.3.2.02,8]deca-6,9-dien-4-one (15719-09-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 4,4'-bis-dimethylamino-benzophenone / Irradiation

2: methanol

With bis(p-dimethylaminophenyl)methanone; In methanol;

DOI:10.1021/jo00905a007

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + tricyclo<3.3.1.02,8>nona-3,6-dien-9-one (6006-24-2) → tricyclo[3.3.2.02,8]deca-6,9-dien-4-one (15719-09-2)

Guidance literature:

In methanol; diethyl ether;

DOI:10.1016/S0040-4020(01)97904-9

upstream raw materials:

diazomethane

tricyclo<3.3.1.0^2,8>nona-3,6-dien-9-one

Bicyclo<4.2.2>deca-2,4,7-trien-9-on

bicyclo[4.2.1]nona-2,4,7-trien-9-one

Downstream raw materials:

Bicyclo<3.3.2>decane

Bicyclo[4.2.2]deca-2.4.9-trien-7-on-tosylhydrazon

Bicyclo<4.2.2>deca-2,4,7,9-tetraen

9-Phenyl-9-hydroxy-tricyclo<3.3.2.0^2,8>decadien-(3,6)

Refernces