Bicyclo[6.3.1]dodeca-1(12),8,10-triene

Base Information

• Chemical Name: Bicyclo[6.3.1]dodeca-1(12),8,10-triene
• CAS No.: 7125-01-1
• Molecular Formula: C12H16
• Molecular Weight: 0
• DSSTox Substance ID: DTXSID50456093
• Nikkaji Number: J14.089I
• Wikidata: Q82278306
• Mol file: 7125-01-1.mol

Synonyms:[6]Metacyclophane;7125-01-1;Bicyclo[6.3.1]dodeca-1(12),8,10-triene;DTXSID50456093

Chemical Property of Bicyclo[6.3.1]dodeca-1(12),8,10-triene

Chemical Property:

• PSA: 0.00000
• LogP: 3.34560
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 160.125200510
• Heavy Atom Count: 12
• Complexity: 114

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCCC2=CC=CC(=C2)CC1

Technology Process of Bicyclo[6.3.1]dodeca-1(12),8,10-triene

There total 10 articles about Bicyclo[6.3.1]dodeca-1(12),8,10-triene 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: 88.0%

endo-10-exo-12-Dichlorotricyclo[6.3.1.0]dodecane (274688-09-4) → [6]Metacyclophane (7125-01-1)

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide; at 20 ℃; for 18h;

DOI:10.1002/(SICI)1521-3765(20000502)6:9<1537::AID-CHEM1537>3.3.CO;2-5

Reference yield: 70.0%

endo-12-Bromo-endo-10-exo-12-dichlorotricyclo[6.3.1.0]dodecane (274688-08-3) → [6]Metacyclophane (7125-01-1) + 12-Bromo[6]metacyclophane (38262-52-1) + 12-Chloro[6]metacyclophane

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide; at 35 ℃; for 3h; Title compound not separated from byproducts;

DOI:10.1002/(SICI)1521-3765(20000502)6:9<1537::AID-CHEM1537>3.3.CO;2-5

Reference yield: 21.0%

<6>-paracyclophane (53011-74-8) → 5,6,7,8,9,10-hexahydrobenzocyclooctene (1076-69-3) + [6]Metacyclophane (7125-01-1) + (8R,12S)-12-(5,6,7,8,9,10-Hexahydro-benzocycloocten-2-yl)-bicyclo[6.2.2]dodeca-1(11),9-diene (135339-94-5)

Guidance literature:

With sulfuric acid; In dichloromethane; for 1.5h; Yield given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/ja00035a049

upstream raw materials:

12-Bromo[6]metacyclophane

<6>-paracyclophane

1,8-Dibromo-bicyclo[6.2.2]dodeca-9,11-diene

endo-10-exo-12-Dichlorotricyclo[6.3.1.0]dodecane

Refernces

• 1、 Tobe, Yoshito,Takemura, Akihiro,Jimbo, Mamoru,Takahashi, Tohru,Kobiro, Kazuya,Kakiuchi, Kiyomi. "Unusual reactivity of bent acenes: Reactions of [6](1,4)naphthalenophane and [6](1,4)anthracenophane with electrophiles". . p. 3479 - 3491. Retrieved 2007/10/02.
• 2、 Tobe, Yoshito,Ueda, Ken-ichi,Kakiuchi, Kiyomi,Odaira, Yoshinobu,Kai, Yasushi,Kasai, Nobutami. "SYNTHESIS, STRUCTURE AND REACTIVITIES OF PARACYCLOPHANES". . p. 1851 - 1858. Retrieved 2007/10/02.