Dibenzo[a,e]cycloocten-5(6H)-one

Base Information

• Chemical Name: Dibenzo[a,e]cycloocten-5(6H)-one
• CAS No.: 3111-86-2
• Molecular Formula: C₁₆H₁₂O
• Molecular Weight: 220.271
• NSC Number: 139237
• DSSTox Substance ID: DTXSID50419244
• Mol file: 3111-86-2.mol

Synonyms:3111-86-2;Dibenzo[a,e]cycloocten-5(6H)-one;NSC139237;SCHEMBL269837;SCHEMBL9212613;DTXSID50419244;AKOS015969536;NSC-139237;(10Z)-tricyclo[10.4.0.0?,?]hexadeca-1(12),4,6,8,10,13,15-heptaen-2-one;(10Z)-Tricyclo[10.4.0.04,9]hexadeca-1(16),4,6,8,10,12,14-heptaen-2-one

Chemical Property of Dibenzo[a,e]cycloocten-5(6H)-one

Chemical Property:

• Vapor Pressure: 2.02E-06mmHg at 25°C
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 220.088815002
• Heavy Atom Count: 17
• Complexity: 318

Purity/Quality:

DIBENZO[A,E]CYCLOOCTEN-5(6H)-ONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=CC=CC=C2C=CC3=CC=CC=C3C1=O
• Isomeric SMILES: C1C2=CC=CC=C2/C=C\C3=CC=CC=C3C1=O

Technology Process of Dibenzo[a,e]cycloocten-5(6H)-one

There total 7 articles about Dibenzo[a,e]cycloocten-5(6H)-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: 72.0%

dibenzosuberenon (2222-33-5) + diazomethyl-trimethyl-silane (18107-18-1) → 6H-dibenzo[a,e]cyclooctatrien-5-one (3111-86-2)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -10 ℃; for 3h;

Reference yield: 72.0%

dibenzosuberenon (2222-33-5) + diazomethyl-trimethyl-silane (18107-18-1) → 5-oxo-5,6-dihydrodibenzocyclooctene (3111-86-2)

Guidance literature:

With boron trifluoride diethyl ether complex; In dichloromethane; at -10 ℃; for 3h; Inert atmosphere;

DOI:10.1002/cbic.201100117

Reference yield:

5,6,11,12-tetrahydro-dibenzo[a,e]cyclooctene (1460-59-9) → 5-oxo-5,6-dihydrodibenzocyclooctene (3111-86-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NBS

2: (i) collidine, DMSO, (ii) H₂O

With N-Bromosuccinimide;

DOI:10.1139/v70-128

upstream raw materials:

dibenzosuberenon

diazomethyl-trimethyl-silane

3-hydroxy-1,2:5,6-dibenzocycloocta-1,5,7-triene

5,6,11,12-tetrahydro-dibenzo[a,e]cyclooctene

Downstream raw materials:

Dibenzocycloocten-5,6-dion

4-dibenzocyclooctynol

11,12-didehydro-5,6-dihydrodibenzo[a,e]cycloocten-5-yl carbonic acid 4-nitrophenyl ester

1-benzyl-8,9-dihydro-1H-dibenzo[3,4:7,8]cycloocta[1,2-d][1,2,3]triazol-8-ol